Recent Development of Peptide Coupling Reagents in Organic Synthesis

Abstract

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Porous polymer particles—A comprehensive guide to synthesis, characterization, functionalization and applications

“…Coupling of an amino acid on a resin carrying -NH 2 groups (Scheme 1) can be completed in less than 1h at room temperature [370] thanks to various efficient catalysts [371] developed over decades. This chemistry is certainly as efficient as any well accepted click reaction.…”

Novel cinnamic acid/4-aminoquinoline conjugates bearing non-proteinogenic amino acids: Towards the development of potential dual action antimalarials

“…Global synthesis yields were modest, due to the low nucleophilicity of the aniline group in 4-amino-7-chloroquinoline (3), a problem that persisted even when using highly effective coupling agents such as PyBroP, PyClocK, PyAOP or PyOxim [26] in step (ii) of Scheme 1. Interestingly, even though the use of 7-aza-1-hydroxybenzotriazole derivatives as PyAOP has been reported to improve yields in couplings involving poor nucleophiles [27], the best yields in step (ii) were achieved when using the most common 1-hydroxybenzotriazole derivative, TBTU, as a coupling agent. The low nucleophilicity of the aniline 4-amino-7-chloroquinoline (3) was also likely responsible for the low yields obtained in the direct coupling of this heterocycle to cinnamic acid derivatives, step (vii) in Scheme 1.…”

Synthesis, Characterization, X-Ray Crystallography, and Antileishmanial Activities of N-Linked and O-Linked Glycopyranosides

“…One major class of glycoprotein oligosaccharides consists ofoligosaccharides linked to asparagine by an amide bond [11,12]. Amides are usually prepared by thermolysis of carboxylic acids with amines, by coupling of carboxylic acids and amines in the presence of a coupling reagent [13] or by prior conversion of the carboxylic acid into a more electrophilic derivative [14]. The concept to add a chiral aglycone moiety such as tartaric acid to prepare glycosides is an active area…”