Outputs (50)

Salivary Antimicrobial Peptide Histatin-5 Does Not Display Zn(II)-Dependent or -Independent Activity against Streptococci (2023)
Journal Article
Stewart, L. J., Hong, Y., Holmes, I. R., Firth, S. J., Ahmed, Y., Quinn, J., …Djoko, K. Y. (2023). Salivary Antimicrobial Peptide Histatin-5 Does Not Display Zn(II)-Dependent or -Independent Activity against Streptococci. ACS Infectious Diseases, 9(3), 631-642. https://doi.org/10.1021/acsinfecdis.2c00578

Histatin-5 (Hst5) is a member of the histatin superfamily of cationic, His-rich, Zn(II)-binding peptides in human saliva. Hst5 displays antimicrobial activity against fungal and bacterial pathogens, often in a Zn(II)-dependent manner. In contrast, he... Read More about Salivary Antimicrobial Peptide Histatin-5 Does Not Display Zn(II)-Dependent or -Independent Activity against Streptococci.

One-pot ester and thioester formation mediated by pentafluoropyridine (PFP) (2022)
Journal Article
Beardmore, L. N., Cobb, S. L., & Brittain, W. D. (2022). One-pot ester and thioester formation mediated by pentafluoropyridine (PFP). Organic and Biomolecular Chemistry, 20(41), 8059-8064. https://doi.org/10.1039/d2ob01268e

Acyl fluorides are valuable synthetic intermediates, but in some cases they can be challenging to handle and difficult to isolate given their susceptibility to degradation. In addition, many reagents utilised to prepare acyl fluorides are incompatibl... Read More about One-pot ester and thioester formation mediated by pentafluoropyridine (PFP).

Aminoacyl chain translocation catalysed by a type II thioesterase domain in an unusual non-ribosomal peptide synthetase (2022)
Journal Article
Wang, S., Brittain, W. D., Zhang, Q., Lu, Z., Tong, M. H., Wu, K., …Deng, H. (2022). Aminoacyl chain translocation catalysed by a type II thioesterase domain in an unusual non-ribosomal peptide synthetase. Nature Communications, 13(1), https://doi.org/10.1038/s41467-021-27512-0

Non-Ribosomal Peptide Synthetases (NRPSs) assemble a diverse range of natural products with important applications in both medicine and agriculture. They consist of several multienzyme subunits that must interact with each other in a highly controlle... Read More about Aminoacyl chain translocation catalysed by a type II thioesterase domain in an unusual non-ribosomal peptide synthetase.

Preparation and thermally-induced self-assembly behaviour of elastin-like peptide side-chain polymer-gold nanoparticle (ESP-GNP) hybrids (2021)
Journal Article
Zong, J., Cobb, S. L., & Cameron, N. R. (2021). Preparation and thermally-induced self-assembly behaviour of elastin-like peptide side-chain polymer-gold nanoparticle (ESP-GNP) hybrids. ARKIVOC, 2021(6), 131 - 147. https://doi.org/10.24820/ark.5550190.p011.589

Thermoresponsive gold nanoparticles were prepared by conjugation of short pentapeptide sequences, containing the elastin-like peptide (ELP) repeat unit Val-Pro-Gly-Val-Gly (VPGVG), to a well-defined active ester prepolymer, poly(pentafluorophenyl acr... Read More about Preparation and thermally-induced self-assembly behaviour of elastin-like peptide side-chain polymer-gold nanoparticle (ESP-GNP) hybrids.

Peptoids with Antibiofilm Activity against the Gram Negative Obligate Anaerobe, Fusobacterium nucleatum (2021)
Journal Article
Toole, J., Bolt, H. L., Marley, J. J., Patrick, S., Cobb, S. L., & Lundy, F. T. (2021). Peptoids with Antibiofilm Activity against the Gram Negative Obligate Anaerobe, Fusobacterium nucleatum. Molecules, 26(16), Article 4741. https://doi.org/10.3390/molecules26164741

Peptoids (oligo N-substituted glycines) are peptide analogues, which can be designed to mimic host antimicrobial peptides, with the advantage that they are resistant to proteolytic degradation. Few studies on the antimicrobial efficacy of peptoids ha... Read More about Peptoids with Antibiofilm Activity against the Gram Negative Obligate Anaerobe, Fusobacterium nucleatum.

Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP) (2021)
Journal Article
Brittain, W. D., & Cobb, S. L. (2021). Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP). Organic Letters, 23(15), https://doi.org/10.1021/acs.orglett.1c01953

This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We... Read More about Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP).

Fengycin A Analogues with Enhanced Chemical Stability and Antifungal Properties (2021)
Journal Article
Gimenez, D., Phelan, A., Murphy, C. D., & Cobb, S. L. (2021). Fengycin A Analogues with Enhanced Chemical Stability and Antifungal Properties. Organic Letters, 23(12), 4672-4676. https://doi.org/10.1021/acs.orglett.1c01387

Fengycins are cyclic lipo-depsipeptides produced by Bacillus spp. that display potent antifungal properties but are chemically unstable. This instability has meant that no total synthesis of any fengycin has been published. Here we report the synthes... Read More about Fengycin A Analogues with Enhanced Chemical Stability and Antifungal Properties.

Quantitative Proteomics Reveals that Hsp90 Inhibition Dynamically Regulates Global Protein Synthesis in Leishmania mexicana (2021)
Journal Article
Karunakaran, K., Sundriyal, S., Perera, H., Cobb, S. L., & Denny, P. W. (2021). Quantitative Proteomics Reveals that Hsp90 Inhibition Dynamically Regulates Global Protein Synthesis in Leishmania mexicana. mSystems, https://doi.org/10.1128/msystems.00089-21

Heat shock protein 90 (Hsp90) is a conserved molecular chaperone responsible for the folding and maturation of nascent proteins. Hsp90 is regarded as a master regulator of protein homeostasis in the cell, and its inhibition affects the functions of a... Read More about Quantitative Proteomics Reveals that Hsp90 Inhibition Dynamically Regulates Global Protein Synthesis in Leishmania mexicana.

Current Synthetic Routes to Peptidyl Mono-Fluoromethyl Ketones (FMKs) and Their Applications (2020)
Journal Article
Lloyd, C. M., Colgin, N., & Cobb, S. L. (2020). Current Synthetic Routes to Peptidyl Mono-Fluoromethyl Ketones (FMKs) and Their Applications. Molecules, 25(23), Article 5601. https://doi.org/10.3390/molecules25235601

Peptidyl mono-fluoromethyl ketones (FMKs) are a class of biologically active molecules that show potential as both protease inhibitors for the treatment of a range of diseases and as chemical probes for the interrogation of cellular processes. This r... Read More about Current Synthetic Routes to Peptidyl Mono-Fluoromethyl Ketones (FMKs) and Their Applications.

Unusual Magnetic Field Responsive Circularly Polarized Luminescence Probes with Highly Emissive Chiral Eu(III) Complexes (2020)
Journal Article
Zhang, J., Dai, L., Webster, A. M., Chan, W. T. K., Cobb, S. L., & Law, G. (2020). Unusual Magnetic Field Responsive Circularly Polarized Luminescence Probes with Highly Emissive Chiral Eu(III) Complexes. Angewandte Chemie International Edition, 60(2), 1004-1010. https://doi.org/10.1002/anie.202012133

Chirality is ubiquitous within biological systems where many of the roles and functions are still undetermined. Given this, there is a clear need to design and develop sensitive chiral optical probes that can function within a biological setting. Her... Read More about Unusual Magnetic Field Responsive Circularly Polarized Luminescence Probes with Highly Emissive Chiral Eu(III) Complexes.

Synthesis of Complex Unnatural Fluorine-Containing Amino Acids (2020)
Journal Article
Brittain, W. D., Lloyd, C. M., & Cobb, S. L. (2020). Synthesis of Complex Unnatural Fluorine-Containing Amino Acids. Journal of Fluorine Chemistry, 239, Article 109630. https://doi.org/10.1016/j.jfluchem.2020.109630

The area of fluorinated amino acid synthesis has seen rapid growth over the past decade. As reports of singly fluorinated natural amino acid derivatives have grown, researchers have turned their attention to develop methodology to access complex prot... Read More about Synthesis of Complex Unnatural Fluorine-Containing Amino Acids.

Recent advances in the development of anti-infective peptoids (2020)
Journal Article
Bicker, K. L., & Cobb, S. L. (2020). Recent advances in the development of anti-infective peptoids. Chemical Communications, 56(76), 11158-11168. https://doi.org/10.1039/d0cc04704j

In the search for new sources of antimicrobials many researchers have investigated antimicrobial peptides (AMPs) as templates for the design of innovative therapeutics. However, efforts to develop AMPs in this area has been severely hampered by their... Read More about Recent advances in the development of anti-infective peptoids.

Unusually high α-proton acidity of prolyl residues in cyclic peptides (2020)
Journal Article
Maguire, O. R., Taylor, B., Higgins, E. M., Rees, M., Cobb, S. L., Simpkins, N. S., …O'Donoghue, A. C. (2020). Unusually high α-proton acidity of prolyl residues in cyclic peptides. Chemical Science, 11(29), 7722-7729. https://doi.org/10.1039/d0sc02508a

The acidity of the α-proton in peptides has an essential role in numerous biochemical reactions and underpins their stereochemical integrity, which is critical to their biological function. We report a detailed kinetic and computational study of the... Read More about Unusually high α-proton acidity of prolyl residues in cyclic peptides.

Protecting Group Controlled Remote Regioselective Electrophilic Aromatic Halogenation Reactions (2020)
Journal Article
Brittain, W. D. G., & Cobb, S. L. (2020). Protecting Group Controlled Remote Regioselective Electrophilic Aromatic Halogenation Reactions. Journal of Organic Chemistry, 85(11), 6862-6871. https://doi.org/10.1021/acs.joc.9b03322

Being able to utilise a protecting group to influence remote regiocontrol offers a simple alternative approach to direct late-stage functionalisation of complex organic molecules. However, protecting groups that have the ability to influence reaction... Read More about Protecting Group Controlled Remote Regioselective Electrophilic Aromatic Halogenation Reactions.

N-Terminal speciation for native chemical ligation (2020)
Journal Article
Maguire, O. R., Zhu, J., Brittain, W. D., Hudson, A. S., Cobb, S. L., & O’Donoghue, A. C. (2020). N-Terminal speciation for native chemical ligation. Chemical Communications, 56(45), 6114-6117. https://doi.org/10.1039/d0cc01604g

Native chemical ligation (NCL) enables the chemical synthesis of peptides via reactions between N-terminal thiolates and C-terminal thioesters under mild, aqueous conditions at pH 7–8. Here we demonstrate quantitatively how thiol speciation at N-term... Read More about N-Terminal speciation for native chemical ligation.

Reactivation of Epstein–Barr virus by a dual-responsive fluorescent EBNA1-targeting agent with Zn2+-chelating function (2019)
Journal Article
Jiang, L., Lung, H. L., Huang, T., Lan, R., Zha, S., Chan, L. S., …Wong, K. (2019). Reactivation of Epstein–Barr virus by a dual-responsive fluorescent EBNA1-targeting agent with Zn2+-chelating function. Proceedings of the National Academy of Sciences, 116(52), 26614-26624. https://doi.org/10.1073/pnas.1915372116

EBNA1 is the only Epstein–Barr virus (EBV) latent protein responsible for viral genome maintenance and is expressed in all EBV-infected cells. Zn2+ is essential for oligomerization of the functional EBNA1. We constructed an EBNA1 binding peptide with... Read More about Reactivation of Epstein–Barr virus by a dual-responsive fluorescent EBNA1-targeting agent with Zn2+-chelating function.

Fluorinated Aromatic Monomers as Building Blocks To Control α-Peptoid Conformation and Structure (2019)
Journal Article
Gimenez, D., Zhou, G., Hurley, M. F., Aguilar, J. A., Voelz, V. A., & Cobb, S. L. (2019). Fluorinated Aromatic Monomers as Building Blocks To Control α-Peptoid Conformation and Structure. Journal of the American Chemical Society, 141(8), 3430-3434. https://doi.org/10.1021/jacs.8b13498

Peptoids are peptidomimetics of interest in the fields of drug development and biomaterials. However, obtaining stable secondary structures is challenging, and designing these requires effective control of the peptoid tertiary amide cis/trans equilib... Read More about Fluorinated Aromatic Monomers as Building Blocks To Control α-Peptoid Conformation and Structure.

Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions (2019)
Journal Article
Brittain, W. D., & Cobb, S. L. (2019). Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions. Organic and Biomolecular Chemistry, 17(8), 2110-2115. https://doi.org/10.1039/c8ob02899k

Phenols are extremely valuable building blocks in the areas of pharmaceuticals, natural products, materials and catalysts. In order to carry out modifications on phenols, the phenolic oxygen is routinely protected to prevent unwanted side reactions.... Read More about Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions.

Synthesis of Antibacterial Nisin–Peptoid Hybrids Using Click Methodology (2018)
Journal Article
Bolt, H., Kleijn, L., Martin, N., & Cobb, S. (2018). Synthesis of Antibacterial Nisin–Peptoid Hybrids Using Click Methodology. Molecules, 23(7), Article 1566. https://doi.org/10.3390/molecules23071566

Antimicrobial peptides and structurally related peptoids offer potential for the development of new antibiotics. However, progress has been hindered by challenges presented by poor in vivo stability (peptides) or lack of selectivity (peptoids). Herei... Read More about Synthesis of Antibacterial Nisin–Peptoid Hybrids Using Click Methodology.

Stabilising Peptoid Helices Using Non‐Chiral Fluoroalkyl Monomers (2018)
Journal Article
Gimenez, D., Aguilar, J., Bromley, E., & Cobb, S. (2018). Stabilising Peptoid Helices Using Non‐Chiral Fluoroalkyl Monomers. Angewandte Chemie International Edition, 57(33), 10549-10553. https://doi.org/10.1002/anie.201804488

Stability towards protease degradation combined with modular synthesis has made peptoids of considerable interest in the fields of chemical biology, medicine, and biomaterials. Given their tertiary amide backbone, peptoids lack the capacity to hydrog... Read More about Stabilising Peptoid Helices Using Non‐Chiral Fluoroalkyl Monomers.

Synthesis of pentafluorosulfanyl (SF5) containing aromatic amino acids (2018)
Journal Article
Grigolato, L., Brittain, W., Hudson, A., Czyzewska, M., & Cobb, S. (2018). Synthesis of pentafluorosulfanyl (SF5) containing aromatic amino acids. Journal of Fluorine Chemistry, 212, 166-170. https://doi.org/10.1016/j.jfluchem.2018.06.006

Herein, a series of aromatic pentafluorosulfanyl (SF5) containing amino acids are reported. A Negishi cross-coupling strategy utilising a catalyst system of Pd(dba)2 and SPhos afforded the aforementioned SF5 amino acids in yields between 32% and 42%.... Read More about Synthesis of pentafluorosulfanyl (SF5) containing aromatic amino acids.

A Direct Route for the Preparation of Fmoc/OtBu Protected Iodotyrosine (2018)
Journal Article
Steer, A., Bolt, H., Brittain, W., & Cobb, S. (2018). A Direct Route for the Preparation of Fmoc/OtBu Protected Iodotyrosine. Tetrahedron Letters, 59(27), 2644-2646. https://doi.org/10.1016/j.tetlet.2018.05.061

Herein the synthesis of an Fmoc/OtBu orthogonally protected iodotyrosine derivative is reported. This has been achieved via a simple two-step process in an overall 58% yield from commercially available Fmoc-Tyr(tBu)-OH. The Fmoc/OtBu orthogonally pro... Read More about A Direct Route for the Preparation of Fmoc/OtBu Protected Iodotyrosine.

Recent Advances in the Synthesis of Peptoid Macrocycles (2018)
Journal Article
Webster, A., & Cobb, S. (2018). Recent Advances in the Synthesis of Peptoid Macrocycles. Chemistry - A European Journal, 24(30), 7560-7573. https://doi.org/10.1002/chem.201705340

Over the past two decades, developing medical applications for peptides has, and continues to be a highly active area of research. At present there are over 60 peptide-based drugs on the market and more than 140 in various stages of clinical trials.... Read More about Recent Advances in the Synthesis of Peptoid Macrocycles.

Negishi cross-couplings in the synthesis of amino acids (2017)
Journal Article
Brittain, W., & Cobb, S. (2018). Negishi cross-couplings in the synthesis of amino acids. Organic and Biomolecular Chemistry, 16(1), 10-20. https://doi.org/10.1039/c7ob02682j

The Negishi cross-coupling is a powerful C–C bond-forming reaction widely utilised in many areas of organic synthesis. This review details the use of Negishi cross-couplings in the synthesis of unnatural amino acids. The application of this reaction... Read More about Negishi cross-couplings in the synthesis of amino acids.

2,2,2-Trifluoroethanol as a Tool to Control Nucleophilic Peptide Arylation (2017)
Journal Article
Gimenez, D., Dose, A., Robson, N., Sandford, G., Cobb, S., & Coxon, C. (2017). 2,2,2-Trifluoroethanol as a Tool to Control Nucleophilic Peptide Arylation. Organic and Biomolecular Chemistry, 15(19), 4081-4085. https://doi.org/10.1039/c7ob00295e

The SNAr arylation of peptides with perfluoroaromatics provides a route by which to install a useful chemical handle that enables both 19F-NMR analysis and further chemical modification. However, chemo-selective arylation in peptides containing multi... Read More about 2,2,2-Trifluoroethanol as a Tool to Control Nucleophilic Peptide Arylation.

The Application of Perfluoroheteroaromatic Reagents in the Preparation of Modified Peptide Systems (2017)
Journal Article
Gimenez, D., Mooney, C., Dose, A., Sandford, G., Coxon, C., & Cobb, S. (2017). The Application of Perfluoroheteroaromatic Reagents in the Preparation of Modified Peptide Systems. Organic and Biomolecular Chemistry, 15(19), 4086-4095. https://doi.org/10.1039/c7ob00283a

The perfluoroheteroaromatic reagent pentafluoropyridine has proved to be a highly reactive electrophile, undergoing SNAr arylation reactions in the presence of a range of nucleophilic peptide side chains (i.e. cysteine, tyrosine, serine and lysine) u... Read More about The Application of Perfluoroheteroaromatic Reagents in the Preparation of Modified Peptide Systems.

EBNA1-targeted probe for the imaging and growth inhibition of tumours associated with the Epstein–Barr virus (2017)
Journal Article
Jiang, L., Lan, R., Huang, T., Chan, C., Li, H., Lear, S., …Wong, K. (2017). EBNA1-targeted probe for the imaging and growth inhibition of tumours associated with the Epstein–Barr virus. Nature Biomedical Engineering, 1, Article 0042. https://doi.org/10.1038/s41551-017-0042

Epstein–Barr nuclear antigen 1 (EBNA1), a dimeric oncoprotein of the Epstein–Barr virus (EBV), is essential for both viral-genome maintenance and the survival of infected cells. Despite EBNA1’s potential as a therapeutic target, tools for the direct... Read More about EBNA1-targeted probe for the imaging and growth inhibition of tumours associated with the Epstein–Barr virus.

Exploring the links between peptoid antibacterial activity and toxicity (2017)
Journal Article
Bolt, H. L., Eggimann, G. A., Jahoda, C. A., Zuckermann, R. N., Sharples, G. J., & Cobb, S. L. (2017). Exploring the links between peptoid antibacterial activity and toxicity. MedChemComm, 8(5), 886-896. https://doi.org/10.1039/c6md00648e

Peptoids are a promising class of antimicrobial agents with reported activities against a range of both Gram-positive and Gram-negative bacteria, fungi and most recently parasites. However, at present the available toxicty data is somewhat limited an... Read More about Exploring the links between peptoid antibacterial activity and toxicity.

Synthesis of Biaryl-Linked Cyclic Peptoids (2017)
Journal Article
Webster, A. M., & Cobb, S. L. (2017). Synthesis of Biaryl-Linked Cyclic Peptoids. Tetrahedron Letters, 58(10), 1010-1014. https://doi.org/10.1016/j.tetlet.2017.01.097

Peptoids, a class of peptidomimetic, have gained considerable attention as potential therapeutic agents due to properties such as biocompatibility and resistance to enzymatic degradation. In linear peptoids, conformational heterogeneity can arise due... Read More about Synthesis of Biaryl-Linked Cyclic Peptoids.

Log D versus HPLC derived hydrophobicity: The development of predictive tools to aid in the rational design of bioactive peptoids (2017)
Journal Article
Bolt, H., Williams, C., Brooks, R., Zuckermann, R., Cobb, S., & Bromley, E. (2017). Log D versus HPLC derived hydrophobicity: The development of predictive tools to aid in the rational design of bioactive peptoids. Biopolymers, 108(4), Article e23014. https://doi.org/10.1002/bip.23014

Hydrophobicity has proven to be an extremely useful parameter in small molecule drug discovery programmes given that it can be used as a predictive tool to enable rational design. For larger molecules, including peptoids, where folding is possible, t... Read More about Log D versus HPLC derived hydrophobicity: The development of predictive tools to aid in the rational design of bioactive peptoids.

Peptoid efficacy against polymicrobial biofilms determined using propidium monoazide-modified quantitative PCR (2016)
Journal Article
Luoa, Y., Bolt, H., Eggimann, G., McAuley, D., McMullan, R., Curran, T., …Lundy, F. (2017). Peptoid efficacy against polymicrobial biofilms determined using propidium monoazide-modified quantitative PCR. ChemBioChem, 18(1), 111-118. https://doi.org/10.1002/cbic.201600381

Biofilms containing C. albicans are responsible for a wide variety of clinical infections. The protective effects of the biofilm matrix, the low metabolic activity of microorganisms within a biofilm and their high mutation rate, significantly enhance... Read More about Peptoid efficacy against polymicrobial biofilms determined using propidium monoazide-modified quantitative PCR.

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity (2016)
Journal Article
Bolt, H., Denny, P., & Cobb, S. (2016). An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity. Journal of Visualized Experiments, 117, Article e54750. https://doi.org/10.3791/54750

This protocol describes the manual solid-phase synthesis of linear peptoids that contain two differently functionalized cationic monomers. In this procedure amino functionalized 'lysine' and guanido functionalized 'arginine' peptoid monomers can be i... Read More about An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity.

Total Chemical Synthesis of Lassomycin and Lassomycin-Amide (2016)
Journal Article
Lear, S., Munshi, T., Hudson, A., Hatton, C., Clardy, J., Mosely, J., …Cobb, S. (2016). Total Chemical Synthesis of Lassomycin and Lassomycin-Amide. Organic and Biomolecular Chemistry, 14(19), 4534-4541. https://doi.org/10.1039/c6ob00631k

Herein we report a practical synthetic route to the lasso peptide lassomycin (1) and C-terminal variant lassomycin-amide (2). The biological evaluation of peptides 1 and 2 against Mycobacterium tuberculosis revealed that neither had any activity agai... Read More about Total Chemical Synthesis of Lassomycin and Lassomycin-Amide.

Enlarging the chemical space of anti-leishmanials: a structure-activity relationship study of peptoids against Leishmania mexicana, a causative agent of cutaneous leishmaniasis (2016)
Journal Article
Bolt, H., Eggimann, G., Denny, P., & Cobb, S. (2016). Enlarging the chemical space of anti-leishmanials: a structure-activity relationship study of peptoids against Leishmania mexicana, a causative agent of cutaneous leishmaniasis. MedChemComm, 7(5), 799-805. https://doi.org/10.1039/c6md00060f

Peptoids, a class of peptide mimetics, have emerged as promising anti-infective agents against a range of bacterial and fungal infections. Recently we have shown peptoids to be novel anti-parasitic and, specifically, anti-leishmanial, compounds. In t... Read More about Enlarging the chemical space of anti-leishmanials: a structure-activity relationship study of peptoids against Leishmania mexicana, a causative agent of cutaneous leishmaniasis.

Pep-Calc.com: a set of web utilities for the calculation of peptide and peptoid properties and automatic mass spectral peak assignment (2016)
Journal Article
Lear, S., & Cobb, S. (2016). Pep-Calc.com: a set of web utilities for the calculation of peptide and peptoid properties and automatic mass spectral peak assignment. Journal of Computer-Aided Molecular Design, 30(3), 271-277. https://doi.org/10.1007/s10822-016-9902-7

The ability to calculate molecular properties such as molecular weights, isoelectric points, and extinction coefficients is vital for scientists using and/or synthesizing peptides and peptoids for research. A suite of two web utilities: Peptide Calcu... Read More about Pep-Calc.com: a set of web utilities for the calculation of peptide and peptoid properties and automatic mass spectral peak assignment.

A practical method for the synthesis of peptoids containing both lysine-type and arginine-type monomers (2015)
Journal Article
Bolt, H., & Cobb, S. (2016). A practical method for the synthesis of peptoids containing both lysine-type and arginine-type monomers. Organic and Biomolecular Chemistry, 14(4), 1211-1215. https://doi.org/10.1039/c5ob02279g

Peptoids are a promising class of peptidomimetics that exhibit the key chemical and physical properties of peptides but without being hampered by susceptibility towards enzymatic degradation. Biologically active peptoids are often designed to be amph... Read More about A practical method for the synthesis of peptoids containing both lysine-type and arginine-type monomers.

Synthesis, Ni(II) Schiff base complexation and structural analysis of fluorinated analogs of the ligand (S)-2-[N-(N′-benzylprolyl)amino]benzophenone (BPB) (2015)
Journal Article
Tatum, N., Yufit, D., Cobb, S., & Coxon, C. (2015). Synthesis, Ni(II) Schiff base complexation and structural analysis of fluorinated analogs of the ligand (S)-2-[N-(N′-benzylprolyl)amino]benzophenone (BPB). Journal of Fluorine Chemistry, 173, 77-83. https://doi.org/10.1016/j.jfluchem.2015.02.007

Herein we report the first X-ray crystal structure of the well-known (S)-l-ala-Ni-BPB complex (1) and compare this with the X-ray crystal structures obtained for two novel fluorinated (S)-l-ala-Ni-BPB complexes (8 and 12) that contain either an S- or... Read More about Synthesis, Ni(II) Schiff base complexation and structural analysis of fluorinated analogs of the ligand (S)-2-[N-(N′-benzylprolyl)amino]benzophenone (BPB).

The Role of Phosphoglycans in the Susceptibility of Leishmania mexicana to the Temporin Family of Anti-Microbial Peptides (2015)
Journal Article
Eggimann, G., Sweeney, K., Bolt, H., Rozatian, N., Cobb, S., & Denny, P. (2015). The Role of Phosphoglycans in the Susceptibility of Leishmania mexicana to the Temporin Family of Anti-Microbial Peptides. Molecules, 20(2), 2775-2785. https://doi.org/10.3390/molecules20022775

Natural product antimicrobial peptides (AMPs) have been proposed as promising agents against the Leishmania species, insect vector borne protozoan parasites causing the neglected tropical disease leishmaniasis. However, recent studies have shown that... Read More about The Role of Phosphoglycans in the Susceptibility of Leishmania mexicana to the Temporin Family of Anti-Microbial Peptides.

Investigating the Anti-leishmanial Effects of Linear Peptoids (2014)
Journal Article
Eggimann, G., Bolt, H., Denny, P., & Cobb, S. (2015). Investigating the Anti-leishmanial Effects of Linear Peptoids. ChemMedChem, 10(3), 233-237. https://doi.org/10.1002/cmdc.201402416

Peptoids, a class of peptide mimetics, have emerged as promising anti-infective agents against a range of bacterial infections. Herein we present the first study of the antiparasitic and specifically the anti-leishmanial properties of linear peptoids... Read More about Investigating the Anti-leishmanial Effects of Linear Peptoids.

Novel fluorinated lipopeptides from Bacillus sp. CS93 via precursor-directed biosynthesis (2014)
Journal Article
O’Connor, N., Hudson, A., Cobb, S., O’Neil, D., Robertson, J., Duncan, V., & Murphy, C. (2014). Novel fluorinated lipopeptides from Bacillus sp. CS93 via precursor-directed biosynthesis. Amino Acids, 46(12), 2745-2752. https://doi.org/10.1007/s00726-014-1830-z

While attempting to improve production of fluoro-iturin A in Bacillus sp. CS93 new mono- and di-fluorinated fengycins were detected in culture supernatants by 19F NMR and tandem mass spectrometry, after incubation of the bacterium with 3-fluoro-l-tyr... Read More about Novel fluorinated lipopeptides from Bacillus sp. CS93 via precursor-directed biosynthesis.

A mild method for the synthesis of a novel dehydrobutyrine-containing amino acid (2014)
Journal Article
Webster, A. M., Coxon, C. R., Kenwright, A. M., Sandford, G., & Cobb, S. L. (2014). A mild method for the synthesis of a novel dehydrobutyrine-containing amino acid. Tetrahedron, 70(31), 4661-4667. https://doi.org/10.1016/j.tet.2014.05.031

Dehydrobutyrine is an amino acid that is present in a range of peptide natural products. Reaction of pentafluoropyridine with threonine and subsequent E1cb-type elimination allowed the preparation of novel dehydrobutyrine-containing amino acids under... Read More about A mild method for the synthesis of a novel dehydrobutyrine-containing amino acid.

Blending gelators to tune gel properties and probe anion-induced disassembly (2014)
Journal Article
Foster, J., Edkins, R., Cameron, G., Colgin, N., Fucke, K., Ridgeway, S., …Steed, J. (2014). Blending gelators to tune gel properties and probe anion-induced disassembly. Chemistry - A European Journal, 20(1), 279-291. https://doi.org/10.1002/chem.201303153

Blending different low molecular weight gelators (LMWGs) provides a convenient route to tune the properties of a gel and incorporate functionalities such as fluorescence. Blending a series of gelators having a common bis-urea motif, and functionalise... Read More about Blending gelators to tune gel properties and probe anion-induced disassembly.

Communication: Autodetachment versus internal conversion from the S1 state of the isolated GFP chromophore anion (2013)
Journal Article
West, C., Hudson, A., Cobb, S., & Verlet, J. (2013). Communication: Autodetachment versus internal conversion from the S1 state of the isolated GFP chromophore anion. The Journal of Chemical Physics, 139(7), https://doi.org/10.1063/1.4819078

The anionic form of p-hydroxybenzylidene-2,3-dimethylimidazolinone (HBDI) has been extensively employed as a model of the chromophore of the green fluorescence protein. The bright S1 excited state HBDI− has a measured lifetime of 1.4 ps in the gas-ph... Read More about Communication: Autodetachment versus internal conversion from the S1 state of the isolated GFP chromophore anion.

Evaluation of two cyclic di-peptides as inhibitors of CCL2 induced chemotaxis (2013)
Journal Article
Saleki, M., Colgin, N., Kirby, J., Cobb, S., & Ali, S. (2013). Evaluation of two cyclic di-peptides as inhibitors of CCL2 induced chemotaxis. MedChemComm, 4(5), 860-864. https://doi.org/10.1039/c3md00043e

Monocyte chemoattractant protein (CCL2) plays a major role in the recruitment of monocytes during inflammation. In this study we analysed properties of synthetic CCL2 inhibitors in inhibiting CCL2 mediated monocyte migration. Using trans-endothelial... Read More about Evaluation of two cyclic di-peptides as inhibitors of CCL2 induced chemotaxis.

Aqueous synthesis of N,S,-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing (2013)
Journal Article
Trmčić, M., Chadbourne, F., Brear, P., Denny, P., Cobb, S., & Hodgson, D. (2013). Aqueous synthesis of N,S,-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing. Organic and Biomolecular Chemistry, 11(16), 2660-2675. https://doi.org/10.1039/c3ob27448a

We recently reported the use of PSCl3 for the thiophosphorylation of alkylamines where the resulting N-thiophosphoramidate ions could be readily S-alkylated (Chem. Commun., 2011, 47, 6156–6158.). Herein we report the development of this methodology u... Read More about Aqueous synthesis of N,S,-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing.

Synthesis and molecular structure of a perfluorinated pyridyl carbanion (2012)
Journal Article
Colgin, N., Tatum, N., Pohl, E., Cobb, S., & Sandford, G. (2012). Synthesis and molecular structure of a perfluorinated pyridyl carbanion. Journal of Fluorine Chemistry, 133, 33-37. https://doi.org/10.1016/j.jfluchem.2011.09.013

Reaction of pentafluoropyridine with sodium nitromethanide allowed the isolation and characterisation of the first perfluorinated pyridyl carbanion system, sodium nitrobis(perfluoropyridin-4-yl)methanide, by X-ray crystallography.

Studies on the antileishmanial properties of the antimicrobial peptides temporin A, B and 1Sa (2011)
Journal Article
Chadbourne, F., Raleigh, C., Ali, H., Denny, P., & Cobb, S. (2011). Studies on the antileishmanial properties of the antimicrobial peptides temporin A, B and 1Sa. Journal of Peptide Science, 17(11), 751-755. https://doi.org/10.1002/psc.1398

Given the paucity and toxicity of available drugs for leishmaniasis, coupled with the advent of drug resistance, the discovery of new therapies for this neglected tropical disease is recognised as being of the utmost urgency. As such antimicrobial pe... Read More about Studies on the antileishmanial properties of the antimicrobial peptides temporin A, B and 1Sa.

Two-photon induced responsive f–f emissive detection of Cyclin A with a europium-chelating peptide. (2011)
Journal Article
Kong, H., Chadbourne, F., Law, G., Li, H., Tam, H., Cobb, S., …Wong, K. (2011). Two-photon induced responsive f–f emissive detection of Cyclin A with a europium-chelating peptide. Chemical Communications, 47(28), 8052-8054. https://doi.org/10.1039/c1cc12811f

Responsive linear and two-photon induced europium emissive probes have been synthesised with a tailor made peptide for the detection of Cyclin A, the hypersensitive Eu emission (Eu-2) gave the real time signalling and also enhanced the two-photon abs... Read More about Two-photon induced responsive f–f emissive detection of Cyclin A with a europium-chelating peptide..

Synthesis and properties of MIDA boronate containing aromatic amino acids: New peptide building blocks (2011)
Journal Article
Colgin, N., Flinn, T., & Cobb, S. (2011). Synthesis and properties of MIDA boronate containing aromatic amino acids: New peptide building blocks. Organic and Biomolecular Chemistry, 9(6), 1864-1870. https://doi.org/10.1039/c0ob00847h

Herein, we report the synthesis of novel phenylalanine and tyrosine derivatives containing a N-methyliminodiacetic acid boronate group. These compounds can be prepared enantiomerically pure, they are stable to column chromatography and they can be st... Read More about Synthesis and properties of MIDA boronate containing aromatic amino acids: New peptide building blocks.

Antimicrobial peptides for leishmaniasis (2010)
Journal Article
Cobb, S., & Denny, P. (2010). Antimicrobial peptides for leishmaniasis. Current opinion in investigational drugs, 11(8), 868-875

Leishmaniasis is a parasitic disease that is endemic to American, African, Asian and southern European countries. More than 350 million individuals in 88 countries are at risk of infection from this neglected tropical disease. No effective vaccinatio... Read More about Antimicrobial peptides for leishmaniasis.