Enzymatic Resolution of Acetoxyalkenylphosphonates and Their Exploitation in the Chemoenzymatic Synthesis of Phosphonic Derivatives of Carbohydrates

Authors

  • G. Guanti,

    1. Dipartimento di Chimica e Chimica Industriale e C.N.R., CSCCCAAssociated to the National Institute of the C.N.R. for the Chemistry of Biological Systems., via Dodecaneso 31, 16146 Genova, Italy, Fax: (+39) 10–353–6118
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  • M. T. Zannetti,

    1. Dipartimento di Chimica e Chimica Industriale e C.N.R., CSCCCAAssociated to the National Institute of the C.N.R. for the Chemistry of Biological Systems., via Dodecaneso 31, 16146 Genova, Italy, Fax: (+39) 10–353–6118
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  • L. Banfi,

    1. Dipartimento di Chimica e Chimica Industriale e C.N.R., CSCCCAAssociated to the National Institute of the C.N.R. for the Chemistry of Biological Systems., via Dodecaneso 31, 16146 Genova, Italy, Fax: (+39) 10–353–6118
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  • R. Riva

    1. Dipartimento di Chimica e Chimica Industriale e C.N.R., CSCCCAAssociated to the National Institute of the C.N.R. for the Chemistry of Biological Systems., via Dodecaneso 31, 16146 Genova, Italy, Fax: (+39) 10–353–6118
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Abstract

The resolution of racemic α-, β-, and γ-hydroxy-ω-alkenylphosphonates was achieved by enzymatic hydrolysis of the corresponding acetates. The optically active alcohols were transformed into β-hydroxyaldehydes and allowed to react with dihydroxyacetone phosphate (DHAP) via enzymatic aldol addition catalyzed by rabbit muscle fructose 1,6-bisphosphate aldolase (FruArab). After enzymatic dephosphorylation, a set of novel sugar phosphonates was obtained.

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