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

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 ca...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2001-08, Vol.343 (6-7), p.682-691
Main Authors: Guanti, G., Zannetti, M. T., Banfi, L., Riva, R.
Format: Article
Language:English
Subjects:
aldol reaction
Aldolase
Carbohydrates
carbohydrates, enzymatic resolution, hydrolases
Derivatives
enzymatic resolution
Fructose
hydrolases
Hydrolysis
Muscles
Optical activity
phosphonates
Synthesis
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/1615-4169(200108)343:6/7<682::AID-ADSC682>3.0.CO;2-A