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PublicationEuropean Journal of Organic Chemistry
Year2018
Volume
Pages386–391
International

Lipase Regioselective O-Acetylations of a myo-Inositol Derivative: Efficient Desymmetrization of 1,3-Di-O-benzyl-myo-inositol

Authors:Roberto Fernandez-Lafuente
Groups of research:Optimización de biocatalizadores y bioprocesos enzimáticos

Marcela F. P. Ribeiro,+[a] Karla C. Pais,+[b]  Barbara S. M. de Jesus,[b] Roberto Fernandez-Lafuente,*[c] Denise M. G. Freire,*[a]  Evelin A. Manoel,*[a][d] and Alessandro B. C. Simas*[b]


[a]      M. F. P. Ribeiro, D. M. G. Freire, E. A. Manoel
Departamento de Bioquímica, Instituto de Química (IQ)
           Universidade Federal do Rio de Janeiro (UFRJ)
CT, bloco A, 5o andar, Ilha do Fundão, 21941-909, Rio de Janeiro, Brazil
E-mail: freire@iq.ufrj.br
 
[b]      B. S. M. de Jesus, A. B. C. Simas
           Instituto de Pesquisas de Produtos Naturais (IPPN)
Universidade Federal do Rio de Janeiro (UFRJ)
           CCS, bloco H, 21941-902, Rio de Janeiro, Brazil.
           E-mail: abcsimas@nppn.ufrj.br
 
[c]       R. Fernadez-Lafuente
           Department of Biocatalysis, ICP-CSIC
           UAM-CSIC
           C/Marie Curie 2, Cantoblanco, 28049, Madrid, Spain
           E-mail: rfl@icp.csic.es
 
[d]       E. A. Manoel
       Departamento de Biotecnologia Farmacêutica,  Faculdade de          
           Farmácia
           Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil.         

           Email: eamanoel@pharma.ufrj.br


Chiral myo-inositol derivatives play key roles in cell-signaling processes. Despite the relevance of these compounds, few syntheses rely on enantioselective catalytic reactions. Even fewer reports describe the use of desymmetrization of myo-inositol derivatives. In fact, most routes involve resolution by derivatization. Thus, a symmetrical partially-protected myo-inositol derivative, 1,3-di-O-benzyl-myo-inositol (1) was employed as a substrate in fast lipase-catalyzed desymmetrization reactions. Among assayed lipases, both Lipozyme RM-IM and Lipozyme TL-IM were effective in catalyzing the formation of chiral acetate, L-(+)-6-O-acetyl-1,3-di-O-benzyl-myo-inositol, L-(+)-2, with high conversion (98-99%) and ee (>99%). Conversely, Novozyme 435 and Lipomod 34P as biocatalysts showed different regioselectivity, leading to the formation of the symmetrical 5-O-acetylated product. We were able to reuse TL-IM lipase for seven times without noticeable reduction of conversion. Acetate L-(+)-2 has good potential as precursor of bioactive myo-inositol and other relevant materials for Cell Biology studies.
Keywords:Inositols, Cyclitols, Enzyme catalysis, Acylation, Desymmetrization, Asymmetric synthesis
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