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Enzymatic Resolution of Acetoxyalkenylphosphonates and Their Exploitation in the Chemoenzymatic Synthesis of Phosphonic Derivatives of Carbohydrates
Author(s) -
Guanti G.,
Zannetti M. T.,
Banfi L.,
Riva R.
Publication year - 2001
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200108)343:6/7<682::aid-adsc682>3.0.co;2-a
Subject(s) - chemistry , aldolase a , aldol reaction , dihydroxyacetone phosphate , enzyme , dihydroxyacetone , enzymatic hydrolysis , dhap , dephosphorylation , hydrolysis , enzyme catalysis , fructose bisphosphate aldolase , organic chemistry , fructose , biocatalysis , stereochemistry , catalysis , reaction mechanism , phosphatase , glycerol
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 (FruA rab ). After enzymatic dephosphorylation, a set of novel sugar phosphonates was obtained.