de.mpg.escidoc.pubman.appbase.FacesBean
Deutsch
 
Hilfe Wegweiser Impressum Kontakt Einloggen
  DetailsucheBrowse

Datensatz

DATENSATZ AKTIONENEXPORT

Freigegeben

Zeitschriftenartikel

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

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

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

Externe Ressourcen
Es sind keine Externen Ressourcen verfügbar
Volltexte (frei zugänglich)
Es sind keine frei zugänglichen Volltexte verfügbar
Ergänzendes Material (frei zugänglich)
Es sind keine frei zugänglichen Ergänzenden Materialien verfügbar
Zitation

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.


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