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Free keywords:
ISOCYANATES; ESTERS; DEPROTECTION; PEPTIDES
Biochemistry & Molecular Biology; Chemistry; protecting groups; enzymatic deprotection; peptides; glucosyloxycarbonyl group;
Abstract:
The development of the tetrabenzylglucosyloxycarbonyl (BGloc)-protecting group as an enzymatically removable urethane protecting function for peptide synthesis is described. BGloc-protected amino acids are readily synthesized by conversion of amino acid allyl esters into the respective isocyanates, subsequent treatment with 2,3,4,6-tetrabenzylglucose and C-terminal allyl ester cleavage. From BGloc masked dipeptide esters, which are accessible by standard methods of peptide chemistry, the N-terminal urethane is selectively cleaved off in high yield via removal of the benzyl ethers by hydrogenation followed by hydrolysis of the urethane by means of alpha- and beta-glucosidase under very mild reaction conditions. (C) 1998 Elsevier Science Ltd.
