Synthesis of LewisX-O-Core-1 threonine: A building block for O-linked LewisX glycopeptides

被引：6

作者：

Sardar, Mohammed Y. R. ^{[1
,2
]}

Krishnamurthy, Venkata R. ^{[1
,2
]}

Park, Simon ^{[1
,2
]}

Mandhapati, Appi Reddy ^{[1
,2
]}

Wever, Walter J. ^{[1
,2
]}

Park, Dayoung ^{[1
,2
]}

Cummings, Richard D. ^{[1
]}

Chaikof, Elliot L. ^{[1
,2
,3
]}

机构：

[1] Harvard Med Sch, Beth Israel Deaconess Med Ctr, Ctr Drug Discovery & Translat Res, Dept Surg, 110 Francis St,Suite 9F, Boston, MA 02215 USA

[2] Harvard Univ, Wyss Inst Biol Inspired Engn, 110 Francis St,Suite 9F, Boston, MA 02115 USA

[3] Harvard Mit Div Hlth Sci & Technol, Cambridge, MA 02139 USA

来源：

CARBOHYDRATE RESEARCH | 2017年 / 452卷

基金：

美国国家卫生研究院;

关键词：

LECTINS DC-SIGN; X TRISACCHARIDE; DENDRITIC CELLS; PORCINE SPERMATOZOA; HUMAN GRANULOCYTES; ADHESION MOLECULE; GP120; BINDING; STEM-CELLS; GLYCOSYLATION; GLYCAN;

D O I：

10.1016/j.carres.2017.10.002

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Lewis(X) (Le(X)) is a branched trisaccharide Gal beta 1 -> 4(Fuc alpha 1 -> 3) GlcNAc that is expressed on many cell surface glycoproteins and plays critical roles in innate and adaptive immune responses. However, efficient synthesis of glycopeptides bearing Le(X) remains a major limitation for structure-function studies of the Le(X) determinant. Here we report a total synthesis of a Le(X) pentasaccharide 1 using a regioselective 1-benzenesulfinyl piperidine/triflic anhydride promoted [ 3 + 2] glycosylation. The presence of an Fmocthreonine amino acid facilitates incorporation of the pentasaccharide in solid phase peptide synthesis, providing a route to diverse O-linked Le(X) glycopeptides. The described approach is broadly applicable to the synthesis of a variety of complex glycopeptides containing O-linked Le(X) or sialyl Lewis(X) (sLe(X)). (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：47 / 53

页数：7

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