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Journal Article

The tetrabenzylglucosyloxycarbonyl(BGloc)-group-A carbohydrate-derived enzyme-labile urethane protecting group

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons98735

Waldmann,  Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

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Citation

Kappes, T., & Waldmann, H. (1997). The tetrabenzylglucosyloxycarbonyl(BGloc)-group-A carbohydrate-derived enzyme-labile urethane protecting group. CARBOHYDRATE RESEARCH, 305(3-4), 341-349. doi:10.1016/S0008-6215(97)00224-3.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-71BC-5
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.