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

共 26 条

[1] Modular Synthesis of Heparan Sulfate Oligosaccharides for Structure-Activity Relationship Studies [J].

Arungundram, Sailaja ;

Al-Mafraji, Kanar ;

Asong, Jinkeng ;

Leach, Franklin E., III ;

Amster, I. Jonathan ;

Venot, Andre ;

Turnbull, Jeremy E. ;

Boons, Geert-Jan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (47) :17394-17405

[2] Heparan sulphate proteoglycans fine-tune mammalian physiology [J].

Bishop, Joseph R. ;

Schuksz, Manuela ;

Esko, Jeffrey D. .

NATURE, 2007, 446 (7139) :1030-1037

[3] Semi-synthesis of chondroitin sulfate-E from chondroitin sulfate-A [J].

Cai, Chao ;

Solakyildirim, Kemal ;

Yang, Bo ;

Beaudet, Julie M. ;

Weyers, Amanda ;

Linhardt, Robert J. ;

Zhang, Fuming .

CARBOHYDRATE POLYMERS, 2012, 87 (01) :822-829

[4]

Capila I, 2002, ANGEW CHEM INT EDIT, V41, P391

[5] Chemoenzymatic synthesis of glycosaminoglycans: Re-creating, re-modeling and re-designing nature's longest or most complex carbohydrate chains [J].

DeAngelis, Paul L. ;

Liu, Jian ;

Linhardt, Robert J. .

GLYCOBIOLOGY, 2013, 23 (07) :764-777

[6] p-Nitrophenyl group for anomeric protection of oligosaccharides, selective oxidative cleavage via p-acetamidophenyl glycosides [J].

Fukase, K ;

Yasukochi, T ;

Nakai, Y ;

Kusumoto, S .

TETRAHEDRON LETTERS, 1996, 37 (19) :3343-3344

[7] Chemoenzymatic synthesis of Gal(beta 1-3)Gal(beta 1-4)Xyl(beta)-L-Ser and Gal(beta 1-3)Gal(beta 1-4)Xyl(beta)-MU by the use of beta-D-galactosidase [J].

Fukase, K ;

Yasukochi, T ;

Suda, Y ;

Yoshida, M ;

Kusumoto, S .

TETRAHEDRON LETTERS, 1996, 37 (37) :6763-6766

[8]

Fukase K., 1996, MOL DIVERS, V2, P182

[9] Oxidation of Benzylic Alcohols to Their Corresponding Carbonyl Compounds Using Ceric Ammonium Nitrate (CAN)/Bronsted Acidic Ionic Liquid [J].

Hajipour, A. R. ;

Khazdooz, L. ;

Ruoho, A. E. .

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2011, 8 (02) :382-387

[10] Synthesis of 3-O-sulfonated heparan sulfate octasaccharides that inhibit the herpes simplex virus type 1 host-cell interaction [J].

Hu, Yu-Peng ;

Lin, Shu-Yi ;

Huang, Cheng-Yen ;

Zulueta, Medel Manuel L. ;

Liu, Jing-Yuan ;

Chang, Wen ;

Hung, Shang-Cheng .

NATURE CHEMISTRY, 2011, 3 (07) :557-563

← 1 2 3 →