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 …

Rapid and efficient protein synthesis through expansion of the native chemical ligation concept

SS Kulkarni, J Sayers, B Premdjee… - Nature Reviews …, 2018 - nature.com
The growing interest in proteins, both in fundamental research and in drug discovery, has
fuelled demand for efficient synthetic methods to access these biomolecules. Although solid …

Desulfurative Borylation of Small Molecules, Peptides, and Proteins

R **g, WC Powell, KJ Fisch… - Journal of the American …, 2023 - ACS Publications
We introduce a direct conversion of alkyl thiols into boronic acids, facilitated by a water-
soluble phosphine, 1, 3, 5-triaza-7-phosphaadamantane (PTA), in conjunction with …

Biocompatible strategies for peptide macrocyclisation

J He, P Ghosh, C Nitsche - Chemical Science, 2024 - pubs.rsc.org
Peptides are increasingly important drug candidates, offering numerous advantages over
conventional small molecules. However, they face significant challenges related to stability …

Enabling Peptide Ligation at Aromatic Junction Mimics via Native Chemical Ligation and Palladium-Mediated S-Arylation

X Lin, RV Nithun, R Samanta, O Harel, M Jbara - Organic Letters, 2023 - ACS Publications
Synthetic strategies to assemble peptide fragments are in high demand to access
homogeneous proteins for various applications. Here, we combined native chemical ligation …

Synthesis of l‐ and d‐Ubiquitin by One‐Pot Ligation and Metal‐Free Desulfurization

YC Huang, CC Chen, S Gao, YH Wang… - … A European Journal, 2016 - Wiley Online Library
Native chemical ligation combined with desulfurization has become a powerful strategy for
the chemical synthesis of proteins. Here we describe the use of a new thiol additive, methyl …

Oxidative deselenization of selenocysteine: applications for programmed ligation at serine

LR Malins, NJ Mitchell, S McGowan… - Angewandte …, 2015 - Wiley Online Library
Despite the unique chemical properties of selenocysteine (Sec), ligation at Sec is an under‐
utilized methodology for protein synthesis. We describe herein an unprecedented protocol …

Visible-light-induced specific desulfurization of cysteinyl peptide and glycopeptide in aqueous solution

XF Gao, JJ Du, Z Liu, J Guo - Organic letters, 2016 - ACS Publications
Visible-light-induced specific desulfurization of cysteinyl peptides has been explored. The
photocatalytic desulfurization catalyzed by Ru (bpy) 32+ can proceed efficiently at room …

Internal activation of peptidyl prolyl thioesters in native chemical ligation

Y Gui, L Qiu, Y Li, H Li, S Dong - Journal of the American …, 2016 - ACS Publications
Prolyl thioesters have shown significantly lower reactivities in native chemical ligation (NCL)
in comparison to that of the alanyl thioester. This report describes a mild and efficient …

Synthesis and utility of β-selenophenylalanine and β-selenoleucine in diselenide–selenoester ligation

X Wang, L Corcilius, B Premdjee… - The Journal of Organic …, 2019 - ACS Publications
The synthesis of suitably protected β-selenophenylalanine and β-selenoleucine amino acids
was accomplished from Garner's aldehyde as a common starting point. These selenoamino …