Chemoenzymatic synthesis of enantiomers of a new retinoid to investigate the role of chirality in the biological response

We have prepared both enantiomers of a new retinoid ( IIa and IIb) partly 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 lanthanide induced shifts...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 1995-12, Vol.5 (23), p.2801-2804
Main Authors: Charpentier, Bruno, Bernardon, Jean-Michel, Diaz, Philippe, Vion, Michèle, Millois, Corinne, Bernard, Bruno, Shroot, Braham
Format: Article
Language:English
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Summary:We have prepared both enantiomers of a new retinoid ( IIa and IIb) partly 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 lanthanide induced shifts NMR experiments on MTPA esters of 4a and 4b. Only the enantiomer (R-(−)- IIa) is active on the differentiation of F9 embryonal teratocarcinoma cells (F9 cells). Only enantiomer (R)-(−)-IIa is active on the differentiation of F9 embryonal carcinoma cells.
ISSN:0960-894X
1464-3405
DOI:10.1016/0960-894X(95)00489-G