New methods for side-chain protection of cysteine.
[reaction: see text]. Cysteine sulfhydryl protection with either the Fmoc or the Fm group was accomplished in one step and in high yield using commercially available FmocCl or FmocOSu, respectively. Mechanisms for the Fmoc to Fm transformations are discussed. Additionally, Fmoc-Cys(Fmoc)-OH (7) was synthesized and used in amide bond forming reactions. The S-Fmoc group is cleaved selectively from peptides containing the N-Fmoc group.
West
C W
CW
Department of Chemistry and School of Pharmacy, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA.
Estiarte
M A
MA
Rich
D H
DH
D002625:Chemistry, Organic / Q000379:methods*; D003545:Cysteine / Q000737:chemistry*; D008956:Models, Chemical; D010455:Peptides / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry
D010455:Peptides; D013438:Sulfhydryl Compounds; D003545:Cysteine