Toward the chemoenzymatic synthesis of heparan sulfate oligosaccharides: oxidative cleavage of p-nitrophenyl group with ceric ammonium salts

被引：11

作者：

Cai, Chao ^{[1
]}

Li, Lingyun ^{[1
]}

Harvey, Cate ^{[1
]}

Liu, Jian ^{[2
]}

Linhardt, Robert J. ^{[1
,3
,4
,5
]}

机构：

[1] Rensselaer Polytech Inst, Dept Chem & Chem Biol, Ctr Biotechnol & Interdisciplinary Studies, Troy, NY 12180 USA

[2] Univ N Carolina, Edelman Sch Pharm, Div Chem Biol & Med Chem, Chapel Hill, NC 27599 USA

[3] Rensselaer Polytech Inst, Ctr Biotechnol & Interdisciplinary Studies, Dept Biol, Troy, NY 12180 USA

[4] Rensselaer Polytech Inst, Ctr Biotechnol & Interdisciplinary Studies, Dept Chem & Biol Engn, Troy, NY 12180 USA

[5] Rensselaer Polytech Inst, Ctr Biotechnol & Interdisciplinary Studies, Dept Biomed Engn, Troy, NY 12180 USA

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 33期

基金：

美国国家卫生研究院;

关键词：

Heparan sulfate oligosaccharides; Chemoenzymatic synthesis; para-Nitrophenyl glucuronic acid; Ceric ammonium salt; Deprotection; LIQUID-CHROMATOGRAPHY; PROTEIN INTERACTIONS; MOLECULAR-WEIGHT; GLYCOSAMINOGLYCANS; GENERATION; SEPARATION;

D O I：

10.1016/j.tetlet.2013.06.044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed an efficient chemoenzymatic synthesis of heparan sulfate oligosaccharides employing the para-nitrophenyl (p-NP) beta-glucuronide as an acceptor compatible with enzymatic elongation and one that significantly simplifies oligosaccharide purification on C-18 resin. Employing ceric ammonium nitrate as oxidative reagent to remove the p-NP group unexpectedly also removed the glucuronic acid residue at the reducing-end, affording a smaller oligosaccharide. The application of ceric ammonium sulfate allowed the removal of the p-NP without concomitant loss of the adjacent glucuronic acid offering a route to longer heparin sulfate oligosaccharide products. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：4471 / 4474

页数：4

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