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1: Bioorg Med Chem Lett. 2002 Aug 5;12(15):1963-5.Click here to read Links

Synthesis and application of an auxiliary group for chemical ligation at the X-gly site.

Vizzavona J, Dick F, Vorherr T.

BACHEM AG, Hauptstrasse 144, CH-4416 Bubendorf, Switzerland.

An efficient synthesis of an auxiliary group, the 2-mercapto-4,5-dimethoxybenzyl (Dmmb) moiety, to form a Gly-building block is presented. The building block was incorporated into peptides to study the reaction with thiobenzyl-activated derivatives. The target peptides have been obtained by standard chemical ligation reaction, followed by TMSBr-assisted cleavage to remove the auxiliary group. Prior to Dmmb removal, under acidic conditions an unexpected rearrangement was observed and evidence for a mechanism is provided.

PMID: 12113819 [PubMed - indexed for MEDLINE]