Stereoselective synthesis of O-serinyl/threoninyl-2-acetamido-2-deoxy-α- or β-glycosides

Lajos Szabó, Jan Ramza, Courtney Langdon, Robin L Polt

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

General glycosidation methodology has been developed which can selectively provide 2-acetamido-2-deoxy-α- or β-glycosides of β-hydroxy-α-amino acid derivatives [glucopyranoside-(8, 43), galactopyranoside- (9, 13), mannopyranoside- (10), lactoside analogs (11, 38) and 3-O-β-galactopyranosyl-mannopyranoside (12)] stereoselectively in excellent yield from the highly nucleophilic α-imino esters (Schiff bases) of l-serine and l-threonine. Various glycosides were converted via their amino and acetamido derivatives to Fmoc-protected serinyl- or threoninyl-glycosides (24-28, 37, 41, 46) which are all suitable building blocks for the solid-phase synthesis of O-glycopeptides. Complete 1H- and 13C-NMR data are provided for all compounds.

Original languageEnglish (US)
Pages (from-to)11-28
Number of pages18
JournalCarbohydrate Research
Volume274
Issue numberC
DOIs
StatePublished - Sep 8 1995

Fingerprint

Glycosides
Mannose
Derivatives
Solid-Phase Synthesis Techniques
Hydroxy Acids
Schiff Bases
Glycopeptides
Threonine
Galactose
Serine
Esters
Nuclear magnetic resonance
Amino Acids

Keywords

  • 2-Acetamido-2-deoxy-glycosides
  • Stereoselective synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry
  • Molecular Biology

Cite this

Stereoselective synthesis of O-serinyl/threoninyl-2-acetamido-2-deoxy-α- or β-glycosides. / Szabó, Lajos; Ramza, Jan; Langdon, Courtney; Polt, Robin L.

In: Carbohydrate Research, Vol. 274, No. C, 08.09.1995, p. 11-28.

Research output: Contribution to journalArticle

Szabó, Lajos ; Ramza, Jan ; Langdon, Courtney ; Polt, Robin L. / Stereoselective synthesis of O-serinyl/threoninyl-2-acetamido-2-deoxy-α- or β-glycosides. In: Carbohydrate Research. 1995 ; Vol. 274, No. C. pp. 11-28.
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