1334709-91-9Relevant academic research and scientific papers
Divergent Synthesis of Heparan Sulfate Oligosaccharides
Dulaney, Steven B.,Xu, Yongmei,Wang, Peng,Tiruchinapally, Gopinath,Wang, Zhen,Kathawa, Jolian,El-Dakdouki, Mohammad H.,Yang, Bo,Liu, Jian,Huang, Xuefei
, p. 12265 - 12279 (2016/01/09)
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.
Divergent heparin oligosaccharide synthesis with preinstalled sulfate esters
Tiruchinapally, Gopinath,Yin, Zhaojun,El-Dakdouki, Mohammad,Wang, Zhen,Huang, Xuefei
supporting information; experimental part, p. 10106 - 10112 (2011/10/18)
Traditional chemical synthesis of heparin oligosaccharides first involves assembly of the full length oligosaccharide backbone followed by sulfation. Herein, we report an alternative strategy in which the O-sulfate was introduced onto glycosyl building blocks as a trichloroethyl ester prior to assembly of the full length oligosaccharide. This allowed divergent preparation of both sulfated and non-sulfated building blocks from common advanced intermediates. The O-sulfate esters were found to be stable during glycosylation as well as typical synthetic manipulations encountered during heparin oligosaccharide synthesis. Furthermore, the presence of sulfate esters in both glycosyl donors and acceptors did not adversely affect the glycosylation yields, which enabled us to assemble multiple heparin oligosaccharides with preinstalled 6-O-sulfates. Copyright
