Facile synthesis of N-Fmoc-serine-S-GlcNAc: a potential molecular probe for the functional study of O-GlcNAc.
A metabolically stable beta-N-acetylglucosaminyl-1-thio-N-Fmoc-serine (S-GlcNAc-Ser) derivative was synthesized in two procedures: one involving a coupling of a readily obtainable 1-pseudo-thiourea of GlcNAc (S-GlcNAc) and iodo-N-Boc-L-alanine benzyl ester, and the other utilizing a modified Mitsunobu reaction of GlcNAc-SH and a serine derivative.
Ohnishi
Y
Y
Department of Pharmacology and Molecular Sciences, Johns Hopkins University School of Medicine, Baltimore, MD 21205, USA.
Ichikawa
M
M
Ichikawa
Y
Y
D000117:Acetylglucosamine / Q000737:chemistry*; D002236:Carbohydrate Conformation; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015335:Molecular Probes / Q000138:chemical synthesis* / Q000737:chemistry*; D013863:Thioglucosides / Q000138:chemical synthesis* / Q000737:chemistry
C414947:2-(benzyloxycarbonyl)-2-(fluorenylmethoxyamino)ethyl N-acetyl-3,4,5-tri-O-acetyl-2-acetamido-2-deoxy-1-thioglucopyranoside; D015335:Molecular Probes; D013863:Thioglucosides; D003545:Cysteine; D000117:Acetylglucosamine