Efficient desymmetrization of 4,6-di-O-benzyl-myo-inositol by Lipozyme TL-IM.
The enantioselective enzymatic desymmetrization of 4,6-di-O-benzyl-myo-inositol, a myo-inositol derivative, was effectively catalyzed by Thermomyces lanuginosus lipase (TL-IM). The product 1D-1-O-acetyl-4,6-di-O-benzyl-myo-inositol, a useful precursor to inositol phosphates, was obtained in excellent yield and enantiomeric excess. Through the investigation of the effects of solvent, biocatalyst load, and temperature, a more economical procedure resulted. The feasibility of biocatalyst reuse was also shown.
Universidade Federal do Rio de Janeiro (UFRJ), Núcleo de Pesquisas de Produtos Naturais (NPPN), CCS, bloco H, Ilha do Fundão, Rio de Janeiro, RJ, Brazil.
Marcela G
MG
Vasconcelos
Universidade Federal do Rio de Janeiro (UFRJ), Núcleo de Pesquisas de Produtos Naturais (NPPN), CCS, bloco H, Ilha do Fundão, Rio de Janeiro, RJ, Brazil.
Raissa H C
RH
Briggs
UFRJ, Instituto de Química, CT, Ilha do Fundão, Rio de Janeiro, RJ, Brazil.
Lucia C S
LC
Aguiar
UFRJ, Instituto de Química, CT, Programa de Pós-Graduação em Bioquímica, Departamento de Bioquímica, Ilha do Fundão, Rio de Janeiro, RJ, Brazil.
Denise M G
DM
Freire
Universidade Federal do Rio de Janeiro (UFRJ), Núcleo de Pesquisas de Produtos Naturais (NPPN), CCS, bloco H, Ilha do Fundão, Rio de Janeiro, RJ, Brazil. Electronic address: abcsimas@nppn.ufr.br.
Alessandro B C
AB
Simas
D001203:Ascomycota / Q000201:enzymology*; D001593:Benzyl Compounds / Q000737:chemistry*; D055162:Biocatalysis; D005656:Fungal Proteins / Q000737:chemistry*; D007294:Inositol / Q000031:analogs & derivatives* / Q000737:chemistry; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D013237:Stereoisomerism
C430284:4,6-di-O-benzyl-myo-inositol; D001593:Benzyl Compounds; D005656:Fungal Proteins; D007294:Inositol; C093666:Lipozyme; D008049:Lipase
Chiral; Desymmetrization; Enantioselectivity; Inositol; TL-IM Lipase; Thermomyces lanuginosus