Native chemical ligation and extended methods: mechanisms, catalysis, scope, and limitations

V Agouridas, O El Mahdi, V Diemer, M Cargoet… - Chemical …, 2019 - ACS Publications
The native chemical ligation reaction (NCL) involves reacting a C-terminal peptide thioester
with an N-terminal cysteinyl peptide to produce a native peptide bond between the two …

Advances in Fmoc solid‐phase peptide synthesis

R Behrendt, P White, J Offer - Journal of Peptide Science, 2016 - Wiley Online Library
Today, Fmoc SPPS is the method of choice for peptide synthesis. Very‐high‐quality Fmoc
building blocks are available at low cost because of the economies of scale arising from …

Rapid labelling and covalent inhibition of intracellular native proteins using ligand-directed N-acyl-N-alkyl sulfonamide

T Tamura, T Ueda, T Goto, T Tsukidate… - Nature …, 2018 - nature.com
Selective modification of native proteins in live cells is one of the central challenges in recent
chemical biology. As a unique bioorthogonal approach, ligand-directed chemistry recently …

Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water

SH Cho, EJ Yoo, I Bae, S Chang - Journal of the American …, 2005 - ACS Publications
It is shown for the first time that N-sulfonyl amides can be efficiently prepared by an
unconventional approach of the hydrative reaction between terminal alkynes, sulfonyl …

Lysine-Reactive N-Acyl-N-aryl Sulfonamide Warheads: Improved Reaction Properties and Application in the Covalent Inhibition of an Ibrutinib-Resistant BTK Mutant

M Kawano, S Murakawa, K Higashiguchi… - Journal of the …, 2023 - ACS Publications
The covalent inhibition of a target protein has gained widespread attention in the field of
drug discovery. Most of the current covalent drugs utilize the high reactivity of cysteines …

9‐Fluorenylmethoxycarbonyl‐based solid‐phase synthesis of peptide α‐thioesters

F Mende, O Seitz - Angewandte Chemie International Edition, 2011 - Wiley Online Library
Peptide thioesters play a key role in convergent protein synthesis strategies such as native
chemical ligation, traceless Staudinger ligation, and Ag+‐mediated thioester ligation. The …

Chemical and biomimetic total syntheses of natural and engineered MCoTI cyclotides

P Thongyoo, N Roqué-Rosell… - Organic & …, 2008 - pubs.rsc.org
The naturally-occurring cyclic cystine-knot microprotein trypsin inhibitors MCoTI-I and MCoTI-
II have been synthesised using both thia-zip native chemical ligation and a biomimetic …

Affinity-guided oxime chemistry for selective protein acylation in live tissue systems

T Tamura, Z Song, K Amaike, S Lee, S Yin… - Journal of the …, 2017 - ACS Publications
Catalyst-mediated protein modification is a powerful approach for the imaging and
engineering of natural proteins. We have previously developed affinity-guided 4 …

Solid phase protein chemical synthesis

L Raibaut, O El Mahdi, O Melnyk - Protein Ligation and Total Synthesis II, 2015 - Springer
The chemical synthesis of peptides or small proteins is often an important step in many
research projects and has stimulated the development of numerous chemical …

N-Acyl-N-alkyl/aryl Sulfonamide Chemistry Assisted by Proximity for Modification and Covalent Inhibition of Endogenous Proteins in Living Systems

T Tamura, I Hamachi - Accounts of Chemical Research, 2024 - ACS Publications
Conspectus Selective chemical modification of endogenous proteins in living systems with
synthetic small molecular probes is a central challenge in chemical biology. Such …