Enzymatic resolution of acetoxyalkenylphosphonates and their exploitation in the chemoenzymatic synthesis of phosphonic derivatives of carbohydrates

Authors
Guanti, G Zannetti, MT Banfi, L Riva, R
Citation
G. Guanti et al., Enzymatic resolution of acetoxyalkenylphosphonates and their exploitation in the chemoenzymatic synthesis of phosphonic derivatives of carbohydrates, ADV SYNTH C, 343(6-7), 2001, pp. 682-691
Citations number
37
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ADVANCED SYNTHESIS & CATALYSIS
ISSN journal
16154150 → ACNP
Volume
343
Issue
6-7
Year of publication
2001
Pages
682 - 691
Database
ISI
SICI code
1615-4150(200108)343:6-7<682:EROAAT>2.0.ZU;2-D
Abstract
The resolution of racemic alpha-, beta-, and gamma -hydroxy-omega -alkenylp hosphonates was achieved by enzymatic hydrolysis of the corresponding aceta tes. The optically active alcohols were transformed into beta -hydroxyaldeh ydes and allowed to react with dihydroxyacetone phosphate (DHAP) via enzyma tic aldol addition catalyzed by rabbit muscle fructose 1,6-bisphosphate ald olase (FruA(rab)). After enzymatic dephosphorylation, a set of novel sugar phosphonates was obtained.