CHEMOENZYMATIC SYNTHESIS OF ENANTIOMERS OF A NEW RETINOID TO INVESTIGATE THE ROLE OF CHIRALITY IN THE BIOLOGICAL RESPONSE

Authors
CHARPENTIER B BERNARDON JM DIAZ P VION M MILLOIS C BERNARD B SHROOT B
Citation
B. Charpentier et al., CHEMOENZYMATIC SYNTHESIS OF ENANTIOMERS OF A NEW RETINOID TO INVESTIGATE THE ROLE OF CHIRALITY IN THE BIOLOGICAL RESPONSE, Bioorganic & medicinal chemistry letters, 5(23), 1995, pp. 2801-2804
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
5
Issue
23
Year of publication
1995
Pages
2801 - 2804
Database
ISI
SICI code
0960-894X(1995)5:23<2801:CSOEOA>2.0.ZU;2-G
Abstract
We have prepared both enantiomers of a new retinoid (IIa and IIb) part ly by using lipase resolution of 1-acetoxy-1-(5, 6, 7, 8 - tetrahydro - 5, 5, 8, 8-tetramethyl-2-naphthyl) ethane. Absolute configuration of resulting secondary carbinols (4a and 4b) was assigned using lanthani de induced shifts NMR experiments on MTPA esters of 4a and 4b. Only th e enantiomer (R-(-)-IIa) is active on the differentiation of F9 embryo nal teratocarcinoma cells (F9 cells).