All 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. (online). 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.