Chemoenzymatic synthesis of unmodified heparin oligosaccharides: cleavage of p-nitrophenyl glucuronide by alkaline and Smith degradation-Reference-Cited by-同舟云学术

Chemoenzymatic synthesis of unmodified heparin oligosaccharides: cleavage of p-nitrophenyl glucuronide by alkaline and Smith degradation

Published:2017 Issue:5 Volume:15 Page:1222-1227
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Zhang Xing¹²³⁴⁵,Xu Yongmei⁶⁷⁸⁹¹⁰,Hsieh Po-Hung⁶⁷⁸⁹¹⁰,Liu Jian⁶⁷⁸⁹¹⁰^ORCID,Lin Lei¹²³⁴⁵,Schmidt Eric P.¹¹¹²¹³¹⁴¹⁵,Linhardt Robert J.¹²³⁴⁵^ORCID

Affiliation:

1. Departments of Chemistry and Chemical Biology

2. Chemical and Biochemical Engineering

3. Biology

4. Biomedical Engineering

5. Rensselaer Polytechnic Institute

6. Division of Chemical Biology and Medicinal Chemistry

7. Eshelman School of Pharmacy

8. University of North Carolina

9. Chapel Hill

10. USA

11. University of Colorado Denver

12. Dept. of Medicine

13. Research Complex 2

14. 12700 E. 19th Avenue

15. Aurora CO 80045 and Denver Health Medical Center

Abstract

A heparin oligosaccharide having a completely natural structure was successfully synthesized through a chemoenzymatic approach using an unnatural glycosyl acceptor, p-nitrophenyl glucuronide (GlcA-pNP).

Funder

National Heart, Lung, and Blood Institute

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2017/OB/C6OB02603F

Reference28 articles.

1. 2003 Claude S. Hudson Award Address in Carbohydrate Chemistry. Heparin: Structure and Activity

2. Synthesis of simple heparanase substrates

3. Heparan sulfate phage display antibodies recognise epitopes defined by a combination of sugar sequence and cation binding

4. Chemoenzymatic synthesis of heparan sulfate and heparin

5. Heparin and related polysaccharides: synthesis using recombinant enzymes and metabolic engineering

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