C-linked glycosyl azido acid in novel solid-phase C-glycopeptide synthesis

Ulf Tedebark; Morten Meldal; Luigi Panza; Klaus Bock

doi:10.1016/S0040-4039(98)00095-1

C-linked glycosyl azido acid in novel solid-phase C-glycopeptide synthesis

Ulf Tedebark
, Morten Meldal
, Luigi Panza
, Klaus Bock

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

Abstract

A C-linked gylosyl decapeptide was synthesized on solid-phase by a combination of the Fmoc-method and a novel method of using azido acids with reductive deprotection. The unprotected C-glycosyl azido acid building block was incorparated by a TBTU coupling, subsequently reduced using DTT in DMF and followed by further Fmoc-amino acid-OPfp ester couplings. Mouse hemoglobin(67-76) carrying the C-linked glycoside in position 72 was prepared as a metabolically stable T-cell glycopeptide antigen.

Original language	English
Pages (from-to)	1815-1818
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	13
DOIs	https://doi.org/10.1016/S0040-4039(98)00095-1
Publication status	Published - 26 Mar 1998
Externally published	Yes

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10.1016/S0040-4039(98)00095-1

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title = "C-linked glycosyl azido acid in novel solid-phase C-glycopeptide synthesis",

abstract = "A C-linked gylosyl decapeptide was synthesized on solid-phase by a combination of the Fmoc-method and a novel method of using azido acids with reductive deprotection. The unprotected C-glycosyl azido acid building block was incorparated by a TBTU coupling, subsequently reduced using DTT in DMF and followed by further Fmoc-amino acid-OPfp ester couplings. Mouse hemoglobin(67-76) carrying the C-linked glycoside in position 72 was prepared as a metabolically stable T-cell glycopeptide antigen.",

author = "Ulf Tedebark and Morten Meldal and Luigi Panza and Klaus Bock",

year = "1998",

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doi = "10.1016/S0040-4039(98)00095-1",

language = "English",

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TY - JOUR

T1 - C-linked glycosyl azido acid in novel solid-phase C-glycopeptide synthesis

AU - Tedebark, Ulf

AU - Meldal, Morten

AU - Panza, Luigi

AU - Bock, Klaus

PY - 1998/3/26

Y1 - 1998/3/26

N2 - A C-linked gylosyl decapeptide was synthesized on solid-phase by a combination of the Fmoc-method and a novel method of using azido acids with reductive deprotection. The unprotected C-glycosyl azido acid building block was incorparated by a TBTU coupling, subsequently reduced using DTT in DMF and followed by further Fmoc-amino acid-OPfp ester couplings. Mouse hemoglobin(67-76) carrying the C-linked glycoside in position 72 was prepared as a metabolically stable T-cell glycopeptide antigen.

AB - A C-linked gylosyl decapeptide was synthesized on solid-phase by a combination of the Fmoc-method and a novel method of using azido acids with reductive deprotection. The unprotected C-glycosyl azido acid building block was incorparated by a TBTU coupling, subsequently reduced using DTT in DMF and followed by further Fmoc-amino acid-OPfp ester couplings. Mouse hemoglobin(67-76) carrying the C-linked glycoside in position 72 was prepared as a metabolically stable T-cell glycopeptide antigen.

UR - https://www.scopus.com/pages/publications/0032568347

U2 - 10.1016/S0040-4039(98)00095-1

DO - 10.1016/S0040-4039(98)00095-1

M3 - Article

SN - 0040-4039

VL - 39

SP - 1815

EP - 1818

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 13

ER -

C-linked glycosyl azido acid in novel solid-phase C-glycopeptide synthesis

Abstract

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