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

Lajos Szabó; Jan Ramza; Courtney Langdon; Robin Polt

doi:10.1016/0008-6215(95)00016-M

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

Lajos Szabó, Jan Ramza, Courtney Langdon, Robin Polt

Research output: Contribution to journal › Article › peer-review

32 Scopus citations

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 language	English (US)
Pages (from-to)	11-28
Number of pages	18
Journal	Carbohydrate Research
Volume	274
Issue number	C
DOIs	https://doi.org/10.1016/0008-6215(95)00016-M
State	Published - Sep 8 1995

Keywords

2-Acetamido-2-deoxy-glycosides
Stereoselective synthesis

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

Access to Document

10.1016/0008-6215(95)00016-M

Cite this

@article{8f5c0fd6eebc4a3ea05fed76a5f42b15,

title = "Stereoselective synthesis of O-serinyl/threoninyl-2-acetamido-2-deoxy-α- or β-glycosides",

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.",

keywords = "2-Acetamido-2-deoxy-glycosides, Stereoselective synthesis",

author = "Lajos Szab{\'o} and Jan Ramza and Courtney Langdon and Robin Polt",

note = "Funding Information: We would like to thank the National Science Foundation (CHE-9201112) and Selectide Corporation,Tucson, Arizona for the support of this work.",

year = "1995",

month = sep,

day = "8",

doi = "10.1016/0008-6215(95)00016-M",

language = "English (US)",

volume = "274",

pages = "11--28",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier Ltd",

number = "C",

}

TY - JOUR

T1 - Stereoselective synthesis of O-serinyl/threoninyl-2-acetamido-2-deoxy-α- or β-glycosides

AU - Szabó, Lajos

AU - Ramza, Jan

AU - Langdon, Courtney

AU - Polt, Robin

N1 - Funding Information: We would like to thank the National Science Foundation (CHE-9201112) and Selectide Corporation,Tucson, Arizona for the support of this work.

PY - 1995/9/8

Y1 - 1995/9/8

N2 - 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.

AB - 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.

KW - 2-Acetamido-2-deoxy-glycosides

KW - Stereoselective synthesis

UR - http://www.scopus.com/inward/record.url?scp=0029093071&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0029093071&partnerID=8YFLogxK

U2 - 10.1016/0008-6215(95)00016-M

DO - 10.1016/0008-6215(95)00016-M

M3 - Article

C2 - 7585702

AN - SCOPUS:0029093071

SN - 0008-6215

VL - 274

SP - 11

EP - 28

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - C

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this