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Dr Will Brittain's Outputs (22)

Synthesis of metal-binding amino acids (2024)
Journal Article
Deck, K. E. V., & Brittain, W. D. G. (online). Synthesis of metal-binding amino acids. Organic and Biomolecular Chemistry, https://doi.org/10.1039/d4ob01326c

The ability for amino acid residues to bind metals underpins the functions of metalloproteins to conduct a plethora of critical processes in living organisms as well as unnatural applications in the fields of catalysis, sensing and medicinal chemistr... Read More about Synthesis of metal-binding amino acids.

Synthesis of atropisomeric phosphino-triazoles and their corresponding gold(i) complexes (2023)
Journal Article
Zhao, Y., Meloni, F., Male, L., Le Duff, C. S., Brittain, W. D. G., Buckley, B. R., & Fossey, J. S. (2023). Synthesis of atropisomeric phosphino-triazoles and their corresponding gold(i) complexes. Organic Chemistry Frontiers, 10(14), 3460-3466. https://doi.org/10.1039/d3qo00322a

The synthesis of atropisomeric phoshino-triazoles is disclosed. It was found that the introduction of a phosphine functionality onto the 5-position of a 1,2,3-triazole ring could be highly restrictive towards the rotation around a triazole-aryl bond.... Read More about Synthesis of atropisomeric phosphino-triazoles and their corresponding gold(i) complexes.

HFO‐1234yf as a CF3 Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones (2023)
Journal Article
Marsh, T. G., Santambrogio, A., Murray, B. J., Boulton, L. T., Aguilar, J. A., Yufit, D. S., Sandford, G., & Brittain, W. D. (2023). HFO‐1234yf as a CF3 Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones. European Journal of Organic Chemistry, 26(11), Article e202300058. https://doi.org/10.1002/ejoc.202300058

Trifluoromethyl ynones derived from the refrigerant gas HFO-1234yf (2,3,3,3-tetrafluoropropene) react with nucleophiles via a Michael-type addition process and the allenolate intermediate formed reacts intramolecularly with a carbonyl group to form h... Read More about HFO‐1234yf as a CF3 Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones.

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., Kyeremeh, K., Jenner, M., Yu, Y., Cobb, S. L., & 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.

Perfluoroaryl and Perfluoroheteroaryl Reagents as Emerging New Tools for Peptide Synthesis, Modification and Bioconjugation (2021)
Journal Article
Brittain, W. D., & Coxon, C. R. (2022). Perfluoroaryl and Perfluoroheteroaryl Reagents as Emerging New Tools for Peptide Synthesis, Modification and Bioconjugation. Chemistry - A European Journal, 28(7), 10-23. https://doi.org/10.1002/chem.202103305

Perfluoroaromatic and perfluoroheteroaromatic reagents have emerged in recent years as powerful reagents for peptide and protein modification. Dominated by their regio- and chemoselective nucleophilic aromatic substitution chemistry under mild condit... Read More about Perfluoroaryl and Perfluoroheteroaryl Reagents as Emerging New Tools for Peptide Synthesis, Modification and Bioconjugation.

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).

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.

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.

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 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.

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.