TY - JOUR
T1 - A short-step chemo-enzymatic synthesis of a precursor for l-nucleosides from d-lyxose
AU - Kitsuda, Kazunori
AU - Calveras, Jordi
AU - Nagai, Yasuhito
AU - Higashi, Toshinori
AU - Sugai, Takeshi
N1 - Funding Information:
The authors thank Professor Vicente Gotor and Dr. Jesús Joglar, of Department of Chemistry, University of Oviedo and Department of Biological Chemistry and Molecular Modeling, Spanish National Research Council (CSIC), for their kindly providing valuable NMR spectra. We are indebted to Amano Enzyme Inc. for lipase PS-IM. Professor Kazuo Umezawa's encouragement on this study was acknowledged with thanks. J. C. thanks Post-Doctoral fellowship from the Japanese Society for the Promotion of Science (No. P07435). This work was supported both by a Grant-in-Aid for Scientific Research (No. 18580106) and “High-Tech Research Center” Project for Private Universities: matching fund subsidy 2006–2011 from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and acknowledged with thanks.
PY - 2009/7
Y1 - 2009/7
N2 - 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.
AB - 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.
KW - Lipase
KW - Regioselective reaction
KW - Stereochemical inversion
KW - d-Lyxose
KW - l-Nucleoside
KW - l-Ribose
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U2 - 10.1016/j.molcatb.2009.02.014
DO - 10.1016/j.molcatb.2009.02.014
M3 - Article
AN - SCOPUS:64649086494
VL - 59
SP - 197
EP - 200
JO - Journal of Molecular Catalysis - B Enzymatic
JF - Journal of Molecular Catalysis - B Enzymatic
SN - 1381-1177
IS - 1-3
ER -