Facile and Stereo-Selective Synthesis of UDP-α-D-xylose and UDP-β-L-arabinose Using UDP-Sugar Pyrophosphorylase

Frontiers in Chemistry

Samuel J. Polizzi¹  Harmon Greenway¹  Shanshan Li²  JiaJia Wang²  Peng G. Wang²  Mohui Wei² 

[1] Chemily, LLC, Atlanta, GA, United States;Department of Chemistry and Center for Diagnostics and Therapeutics, Georgia State University, Atlanta, GA, United States;Joint National Laboratory for Antibody Drug Engineering, School of Basic Medical Science, Henan University, Kaifeng, China;

关键词: UDP-xylose;    UDP-arabinose;    nucleotide sugar;    chemo-enzymatic synthesis;    UDP-sugar pyrophosphorylase;   

DOI  :  10.3389/fchem.2018.00163

来源: DOAJ

【 摘 要 】

A novel synthesis of nucleotide sugars was conducted to prepare UDP-α-D-xylose and UDP-β-L-arabinose without utilizing protection strategies or advanced purification techniques. Sugar-1-phosphates of D-xylose and L-arabinose were synthesized from their β-glycosylsulfonylhydrazides and evaluated as substrates for recombinant UDP-sugar pyrophosphorylases from Arabidopsis thaliana or Bifidobacterium infantis to furnish the biologically active nucleotide. The facile, three-step procedure takes advantage of substrate diversity available through chemical synthesis followed by the selectivity of enzyme catalysis. This approach increases the substrate scope of enzymatic preparation and expands access to stereopure nucleotide sugars on preparative scale. Increased production of both sugars has implications for glycoengineering and glycan production using glycosyltransferases.

【 授权许可】

Unknown