An insight into the radical thiol/yne coupling: the emergence of arylalkyne-tagged sugars for the direct photoinduced glycosylation of cysteine-containing peptides

…, A Monesi, D Nanni, P Spagnolo…

Index: Benati, Luisa; Bencivenni, Giorgio; Leardini, Rino; Minozzi, Matteo; Nanni, Daniele; Scialpi, Rosanna; Spagnolo, Piero; Zanardi, Giuseppe Journal of Organic Chemistry, 2006 , vol. 71, # 8 p. 3192 - 3197

Full Text: HTML

Citation Number: 51

Abstract

An explorative study of the Thiol− Yne Coupling (TYC) reaction has been carried out using an aliphatic (1-octyne) and an aromatic alkyne (phenylacetylene) and two alkanethiols (methyl thioglycolate and N-acetyl-l-cysteine methyl ester). The outcomes of the TYC reactions strongly depend on the experimental conditions (eg, temperature, solvent, and alkyne/thiol ratio), but these can be properly adjusted to achieve selective production of ...