Chemical synthesis of α-D-mannosylphosphate serine derivatives: A new class of synthetic glycopeptides

Galal A. Elsayed; Geert J. Boons

Chemical synthesis of α-D-mannosylphosphate serine derivatives: A new class of synthetic glycopeptides

^*Corresponding author for this work

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

Abstract

α-D-Mannosylphosphate serine derivatives were conveniently synthesized by reaction of benzyl or cyanoethyl phosphochloroamidites with 2,3,4,6-tetra-O-acetyl-D-mannose to give intermediate α-mannosyl phosphoramidites, which were successfully reacted with properly protected serine derivatives in the presence of 1H-tetrazole to give phosphite triesters which could be oxidized to phosphotriesters using t-BuOOH.

Original language	English
Pages (from-to)	1373-1375
Number of pages	3
Journal	Synlett
Issue number	9 SPEC. ISS.
Publication status	Published - 28 Jul 2003
Externally published	Yes

Keywords

Carbohydrates
Glycopeptides
Glycosyl phosphates
Phosphochloroamidites
Phosphoglycosylation

Cite this

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title = "Chemical synthesis of α-D-mannosylphosphate serine derivatives: A new class of synthetic glycopeptides",

abstract = "α-D-Mannosylphosphate serine derivatives were conveniently synthesized by reaction of benzyl or cyanoethyl phosphochloroamidites with 2,3,4,6-tetra-O-acetyl-D-mannose to give intermediate α-mannosyl phosphoramidites, which were successfully reacted with properly protected serine derivatives in the presence of 1H-tetrazole to give phosphite triesters which could be oxidized to phosphotriesters using t-BuOOH.",

keywords = "Carbohydrates, Glycopeptides, Glycosyl phosphates, Phosphochloroamidites, Phosphoglycosylation",

author = "Elsayed, {Galal A.} and Boons, {Geert J.}",

year = "2003",

month = jul,

day = "28",

language = "English",

pages = "1373--1375",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "9 SPEC. ISS.",

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T1 - Chemical synthesis of α-D-mannosylphosphate serine derivatives

T2 - A new class of synthetic glycopeptides

AU - Elsayed, Galal A.

AU - Boons, Geert J.

PY - 2003/7/28

Y1 - 2003/7/28

N2 - α-D-Mannosylphosphate serine derivatives were conveniently synthesized by reaction of benzyl or cyanoethyl phosphochloroamidites with 2,3,4,6-tetra-O-acetyl-D-mannose to give intermediate α-mannosyl phosphoramidites, which were successfully reacted with properly protected serine derivatives in the presence of 1H-tetrazole to give phosphite triesters which could be oxidized to phosphotriesters using t-BuOOH.

AB - α-D-Mannosylphosphate serine derivatives were conveniently synthesized by reaction of benzyl or cyanoethyl phosphochloroamidites with 2,3,4,6-tetra-O-acetyl-D-mannose to give intermediate α-mannosyl phosphoramidites, which were successfully reacted with properly protected serine derivatives in the presence of 1H-tetrazole to give phosphite triesters which could be oxidized to phosphotriesters using t-BuOOH.

KW - Carbohydrates

KW - Glycopeptides

KW - Glycosyl phosphates

KW - Phosphochloroamidites

KW - Phosphoglycosylation

UR - http://www.scopus.com/inward/record.url?scp=0037765465&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0037765465

SN - 0936-5214

SP - 1373

EP - 1375

JO - Synlett

JF - Synlett

IS - 9 SPEC. ISS.

ER -

Chemical synthesis of α-D-mannosylphosphate serine derivatives: A new class of synthetic glycopeptides

Abstract

Keywords

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