TY - JOUR
T1 - Chemoenzymatic synthesis of enantiomers of a new retinoid to investigate the role of chirality in the biological response
AU - Charpentier, Bruno
AU - Bernardon, Jean Michel
AU - Diaz, Philippe
AU - Vion, Michèle
AU - Millois, Corinne
AU - Bernard, Bruno
AU - Shroot, Braham
PY - 1995/12/7
Y1 - 1995/12/7
N2 - 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).
AB - 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).
UR - http://www.scopus.com/inward/record.url?scp=0028793183&partnerID=8YFLogxK
U2 - 10.1016/0960-894X(95)00489-G
DO - 10.1016/0960-894X(95)00489-G
M3 - Article
AN - SCOPUS:0028793183
SN - 0960-894X
VL - 5
SP - 2801
EP - 2804
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 23
ER -