Facile and Stereo-Selective Synthesis of UDP-α-D-xylose and UDP-β-L-arabinose Using UDP-Sugar Pyrophosphorylase
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 s...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Frontiers Media S.A.
2018-05-01
|
| Series: | Frontiers in Chemistry |
| Subjects: | |
| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2018.00163/full |
| _version_ | 1819131366488408064 |
|---|---|
| author | JiaJia Wang JiaJia Wang Harmon Greenway Harmon Greenway Shanshan Li Mohui Wei Samuel J. Polizzi Peng G. Wang |
| author_facet | JiaJia Wang JiaJia Wang Harmon Greenway Harmon Greenway Shanshan Li Mohui Wei Samuel J. Polizzi Peng G. Wang |
| author_sort | JiaJia Wang |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-22T09:14:22Z |
| format | Article |
| id | doaj.art-b964e10cdf8149a1a8c8f2670e0f19a2 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-22T09:14:22Z |
| publishDate | 2018-05-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-b964e10cdf8149a1a8c8f2670e0f19a22022-12-21T18:31:21ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462018-05-01610.3389/fchem.2018.00163357213Facile and Stereo-Selective Synthesis of UDP-α-D-xylose and UDP-β-L-arabinose Using UDP-Sugar PyrophosphorylaseJiaJia Wang0JiaJia Wang1Harmon Greenway2Harmon Greenway3Shanshan Li4Mohui Wei5Samuel J. Polizzi6Peng G. Wang7Joint National Laboratory for Antibody Drug Engineering, School of Basic Medical Science, Henan University, Kaifeng, ChinaDepartment of Chemistry and Center for Diagnostics and Therapeutics, Georgia State University, Atlanta, GA, United StatesDepartment of Chemistry and Center for Diagnostics and Therapeutics, Georgia State University, Atlanta, GA, United StatesChemily, LLC, Atlanta, GA, United StatesDepartment of Chemistry and Center for Diagnostics and Therapeutics, Georgia State University, Atlanta, GA, United StatesDepartment of Chemistry and Center for Diagnostics and Therapeutics, Georgia State University, Atlanta, GA, United StatesChemily, LLC, Atlanta, GA, United StatesDepartment of Chemistry and Center for Diagnostics and Therapeutics, Georgia State University, Atlanta, GA, United StatesA 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.https://www.frontiersin.org/article/10.3389/fchem.2018.00163/fullUDP-xyloseUDP-arabinosenucleotide sugarchemo-enzymatic synthesisUDP-sugar pyrophosphorylase |
| spellingShingle | JiaJia Wang JiaJia Wang Harmon Greenway Harmon Greenway Shanshan Li Mohui Wei Samuel J. Polizzi Peng G. Wang Facile and Stereo-Selective Synthesis of UDP-α-D-xylose and UDP-β-L-arabinose Using UDP-Sugar Pyrophosphorylase Frontiers in Chemistry UDP-xylose UDP-arabinose nucleotide sugar chemo-enzymatic synthesis UDP-sugar pyrophosphorylase |
| title | Facile and Stereo-Selective Synthesis of UDP-α-D-xylose and UDP-β-L-arabinose Using UDP-Sugar Pyrophosphorylase |
| title_full | Facile and Stereo-Selective Synthesis of UDP-α-D-xylose and UDP-β-L-arabinose Using UDP-Sugar Pyrophosphorylase |
| title_fullStr | Facile and Stereo-Selective Synthesis of UDP-α-D-xylose and UDP-β-L-arabinose Using UDP-Sugar Pyrophosphorylase |
| title_full_unstemmed | Facile and Stereo-Selective Synthesis of UDP-α-D-xylose and UDP-β-L-arabinose Using UDP-Sugar Pyrophosphorylase |
| title_short | Facile and Stereo-Selective Synthesis of UDP-α-D-xylose and UDP-β-L-arabinose Using UDP-Sugar Pyrophosphorylase |
| title_sort | facile and stereo selective synthesis of udp α d xylose and udp β l arabinose using udp sugar pyrophosphorylase |
| topic | UDP-xylose UDP-arabinose nucleotide sugar chemo-enzymatic synthesis UDP-sugar pyrophosphorylase |
| url | https://www.frontiersin.org/article/10.3389/fchem.2018.00163/full |
| work_keys_str_mv | AT jiajiawang facileandstereoselectivesynthesisofudpadxyloseandudpblarabinoseusingudpsugarpyrophosphorylase AT jiajiawang facileandstereoselectivesynthesisofudpadxyloseandudpblarabinoseusingudpsugarpyrophosphorylase AT harmongreenway facileandstereoselectivesynthesisofudpadxyloseandudpblarabinoseusingudpsugarpyrophosphorylase AT harmongreenway facileandstereoselectivesynthesisofudpadxyloseandudpblarabinoseusingudpsugarpyrophosphorylase AT shanshanli facileandstereoselectivesynthesisofudpadxyloseandudpblarabinoseusingudpsugarpyrophosphorylase AT mohuiwei facileandstereoselectivesynthesisofudpadxyloseandudpblarabinoseusingudpsugarpyrophosphorylase AT samueljpolizzi facileandstereoselectivesynthesisofudpadxyloseandudpblarabinoseusingudpsugarpyrophosphorylase AT penggwang facileandstereoselectivesynthesisofudpadxyloseandudpblarabinoseusingudpsugarpyrophosphorylase |