Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides

被引：48

作者：

Cai, Chao ^{[1
]}

Dickinson, Demetria M. ^{[1
]}

Li, Lingyun ^{[1
]}

Masuko, Sayaka ^{[1
]}

Suflita, Matt ^{[2
]}

Schultz, Victor ^{[1
]}

Nelson, Shawn D. ^{[1
]}

Bhaskar, Ujjwal ^{[1
]}

Liu, Jian ^{[5
]}

Linhardt, Robert J. ^{[1
,2
,3
,4
]}

机构：

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

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

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

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

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

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 08期

基金：

美国国家卫生研究院;

关键词：

ENZYMATIC-SYNTHESIS; TAGS; STRATEGY; PURIFICATION; BINDING;

D O I：

10.1021/ol500738g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag. attached at the reducing end is reported. The fluorous tert-butyl dicarbonate ((F)Boc) tag did not interfere with enzymatic recognition for both elongation and specific sulfation, and flash purification was performed by standard fluorous solid-phase extraction (FSPE). Based on an (F)Boc attached disaccharide as acceptor, a series of partial N-sulfated, 6-O-sulfated heparan sulfate. oligosaccharides were successfully synthesized employing fluorous techniques.

引用

页码：2240 / 2243

页数：4

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