Abstract
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.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Acetylglucosamine / chemistry*
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Carbohydrate Conformation
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Cysteine / analogs & derivatives*
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Cysteine / chemical synthesis
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Cysteine / chemistry
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Molecular Probes / chemical synthesis*
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Molecular Probes / chemistry*
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Thioglucosides / chemical synthesis*
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Thioglucosides / chemistry
Substances
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2-(benzyloxycarbonyl)-2-(fluorenylmethoxyamino)ethyl N-acetyl-3,4,5-tri-O-acetyl-2-acetamido-2-deoxy-1-thioglucopyranoside
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Molecular Probes
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Thioglucosides
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Cysteine
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Acetylglucosamine