127605-76-9Relevant articles and documents
The Use of Crown Ethers in Peptide Chemistry. Part 2. Syntheses of Dipeptide Complexes with Cyclic Polyether 18-Crown-6 and their Derivatisation with DMSO
Hyde, Carolyn B.,Welham, Kevin J.,Mascagni, Paolo
, p. 2011 - 2016 (2007/10/02)
As part of a study the aim of which is to use crown compounds as non-covalent protecting groups in peptide synthesis, we have explored the reactivity of 18-crown-6-ether-dipeptide complexes with dicyclohexylcarbodi-imide (DCC) in dimethyl sulphoxide (DMSO).At a reactant concentration of ca. 0.02 mol dm-3 the DCC did not activate the dipeptide, and the N-acylurea derivative slowly formed.At concentrations of ca. 0.2 mol dm-3 the complexes proved to be unstable and reacted with the solvent to form a DMSO-peptide adduct.The reaction mechanism leading to the latter was elucidated and shown to involve an initial acid-catalysed addition of DMSO to DCC.The presence in solution of nucleophiles gave the peptide ester thus indicating DCC-mediated activation of the peptide carboxylic acid group.The results from this study were used to design the conditions necessary for an effective non-covalent protection of the amino group during peptide synthesis.