English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
Add to Basket
  Local TagsRelease HistoryDetailsSummary

Released
Journal Article

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

MPS-Authors
/persons/resource/persons98735

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

External Resource
No external resources are shared
Fulltext (restricted access)
There are currently no full texts shared for your IP range.
Fulltext (public)
There are no public fulltexts stored in PuRe
Supplementary Material (public)
There is no public supplementary material available
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: https://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.