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 …

Nonclassical routes for amide bond formation

RM De Figueiredo, JS Suppo, JM Campagne - Chemical reviews, 2016 - ACS Publications
The present review offers an overview of nonclassical (eg, with no pre-or in situ activation of
a carboxylic acid partner) approaches for the construction of amide bonds. The review aims …

Drug delivery systems, CNS protection, and the blood brain barrier

RK Upadhyay - BioMed research international, 2014 - Wiley Online Library
Present review highlights various drug delivery systems used for delivery of pharmaceutical
agents mainly antibiotics, antineoplastic agents, neuropeptides, and other therapeutic …

Developments in peptide and amide synthesis

F Albericio - Current opinion in chemical biology, 2004 - Elsevier
The solid-phase methodology is key for an effective synthesis of peptides, from a milligram
scale for research to a multi-kilo scale for drug production. Indeed, small peptides containing …

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 …

N-Alkyl cysteine-assisted thioesterification of peptides

H Hojo, Y Onuma, Y Akimoto, Y Nakahara… - Tetrahedron …, 2007 - Elsevier
A new method for the preparation of peptide thioester by the post-solid phase peptide
synthesis (SPPS) approach was developed. A series of N-alkyl cysteine derivatives were …

Glycopeptides as versatile tools for glycobiology

T Buskas, S Ingale, GJ Boons - Glycobiology, 2006 - academic.oup.com
This review describes the recent advances in the field of glycopeptide and small
glycoprotein synthesis. The strategies covered include chemical and chemoenzymatic …

Native chemical ligation through in situ O to S acyl shift

P Botti, M Villain, S Manganiello, H Gaertner - Organic letters, 2004 - ACS Publications
A novel strategy to generate thioester peptides compatible with Fmoc chemistry is
presented. Peptide-Cαoxy-(2-mercapto-1-carboxyamide) ethyl ester undergoes an O to S …

Peptidyl N,N-Bis(2-mercaptoethyl)-amides as Thioester Precursors for Native Chemical Ligation

W Hou, X Zhang, F Li, CF Liu - Organic letters, 2011 - ACS Publications
With two β-mercaptoethyl groups on the N, a tertiary amide of structure 1 is always poised for
intramolecular thioesterification however it flips about the C− N bond. It is shown that a …

NS Acyl-Transfer-Mediated Synthesis of Peptide Thioesters Using Anilide Derivatives

S Tsuda, A Shigenaga, K Bando, A Otaka - Organic Letters, 2009 - ACS Publications
N→ S acyl-transfer-mediated synthesis of peptide thioesters utilizing an N-aminoacyl-N-
sulfanylethylaminobenzoic acid derivative has been examined. The developed synthetic …