Transketolase-mediated synthesis of 4-deoxy-D-fructose 6-phosphate by epoxide hydrolase-catalysed resolution of 1,1-diethoxy-3,4-epoxybutane

Authors
Guerard, C Alphand, V Archelas, A Demuynck, C Hecquet, L Furstoss, R Bolte, J
Citation
C. Guerard et al., Transketolase-mediated synthesis of 4-deoxy-D-fructose 6-phosphate by epoxide hydrolase-catalysed resolution of 1,1-diethoxy-3,4-epoxybutane, EUR J ORG C, (12), 1999, pp. 3399-3402
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
12
Year of publication
1999
Pages
3399 - 3402
Database
ISI
SICI code
1434-193X(199912):12<3399:TSO46B>2.0.ZU;2-0
Abstract
4-Deoxy-D-fructose 6-phosphate is synthesised from nonnatural sources in fo ur steps, including two enzymatic reactions. (3S)-1,1-Diethoxy-3,4-epoxybut ane is first obtained by epoxide hydrolase-catalysed resolution. Opening of this epoxide by inorganic phosphate leads to 2-deoxy-D-erythrose 4-phospha te. In the last step, transketolase transfers a hydroxyacetyl group from L- erythrulose onto this aldehyde, controlling the second asymmetric center.