Synthesis of a mimic for the heterogeneous surface of core 2 sialoglycan-linked glycoprotein

Yutaka Takano; Hironobu Hojo; Naoya Kojima; Yoshiaki Nakahara

doi:10.1021/ol048827b

Synthesis of a mimic for the heterogeneous surface of core 2 sialoglycan-linked glycoprotein

Org Lett. 2004 Sep 2;6(18):3135-8. doi: 10.1021/ol048827b.

Authors

Yutaka Takano¹, Hironobu Hojo, Naoya Kojima, Yoshiaki Nakahara

Affiliation

¹ Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University, Kitakaname 1117, Hiratsuka, Kanagawa, 259-1292, Japan.

PMID: 15330606
DOI: 10.1021/ol048827b

Abstract

[structure: see text] An O-glycosylated peptide carrying two core 2 sialopentasaccharides of different glycoform was synthesized as a model of the heterogeneous surface of mucin glycoprotein. Solid-phase synthesis and the subsequent enzymatic sialylation gave two segments, which were coupled by selective thioester activation to produce the title compound.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antigens, CD / chemistry
Catalysis
Glycoproteins / analysis
Glycoproteins / chemical synthesis*
Glycoproteins / chemistry*
Humans
Indicators and Reagents
Leukosialin
Molecular Mimicry
Molecular Structure
Peptide Fragments / analysis
Peptide Fragments / chemical synthesis*
Peptide Fragments / chemistry
Sialoglycoproteins / chemical synthesis*
Sialoglycoproteins / chemistry
Sialyltransferases / metabolism

Substances

Antigens, CD
Glycoproteins
Indicators and Reagents
Leukosialin
Peptide Fragments
SPN protein, human
Sialoglycoproteins
Sialyltransferases