Abstract
A new chemo-enzymatic route to tetra-O-acetyl-l-ribofuranose from d-lyxose is described. Lipase-catalyzed regioselective transesterification of acetate proceeded on C-4 of the d-lyxopyranoside. Subsequently, stereochemistry of liberated secondary alcohol was inverted by way of oxidation and reduction by IBX and NaBH(OAc)3 to give l-ribopyranoside. After deprotection, the furanose-pyranose isomeric mixture was converged to the target molecule, taking advantage of lipase-catalyzed preferential acetylation of primary alcohol on C-5.
| Original language | English |
|---|---|
| Pages (from-to) | 197-200 |
| Number of pages | 4 |
| Journal | Journal of Molecular Catalysis B: Enzymatic |
| Volume | 59 |
| Issue number | 1-3 |
| DOIs | |
| Publication status | Published - 2009 Jul 1 |
Keywords
- Lipase
- Regioselective reaction
- Stereochemical inversion
- d-Lyxose
- l-Nucleoside
- l-Ribose
ASJC Scopus subject areas
- Catalysis
- Bioengineering
- Biochemistry
- Process Chemistry and Technology
Fingerprint Dive into the research topics of 'A short-step chemo-enzymatic synthesis of a precursor for l-nucleosides from d-lyxose'. Together they form a unique fingerprint.
Cite this
Kitsuda, K., Calveras, J., Nagai, Y., Higashi, T., & Sugai, T. (2009). A short-step chemo-enzymatic synthesis of a precursor for l-nucleosides from d-lyxose. Journal of Molecular Catalysis B: Enzymatic, 59(1-3), 197-200. https://doi.org/10.1016/j.molcatb.2009.02.014