期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 24, 页码 12265-12279出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02172
关键词
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资金
- National Science Foundation [CHE 1507226]
- National Institute of General Medical Sciences, NIH [R01GM072667, U01GM116262, U01GM102137]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1507226] Funding Source: National Science Foundation
Heparan sulfates are implicated in a wide range of biological processes. A major challenge in deciphering their structure and activity relationship is the synthetic difficulties to access diverse heparan sulfate oligosaccharides with well-defined sulfation patterns. In order to expedite the synthesis, a divergent synthetic strategy was developed. By integrating chemical synthesis and two types of O-sulfo transferases, seven different hexasaccharides were obtained from a single hexasaccharide precursor. This approach combined the flexibility of chemical synthesis with the selectivity of enzyme-catalyzed sulfations, thus simplifying the overall synthetic operations. In an attempt to establish structure activity relationships of heparan sulfate binding with its receptor, the synthesized oligosaccharides were incorporated onto a glycan microarray, and their bindings with a growth factor FGF-2 were examined. The unique combination of chemical and enzymatic approaches expanded the capability of oligosaccharide synthesis. In addition, the well-defined heparan sulfate structures helped shine light on the fine substrate specificities of biosynthetic enzymes and confirm the potential sequence of enzymatic reactions in biosynthesis.
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