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

Bruno Charpentier; Jean Michel Bernardon; Philippe Diaz; Michèle Vion; Corinne Millois; Bruno Bernard; Braham Shroot

doi:10.1016/0960-894X(95)00489-G

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

Bruno Charpentier
, Jean Michel Bernardon
, Philippe Diaz
, Michèle Vion
, Corinne Millois
, Bruno Bernard
, Braham Shroot

Galderma

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

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).

Original language	English
Pages (from-to)	2801-2804
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	5
Issue number	23
DOIs	https://doi.org/10.1016/0960-894X(95)00489-G
State	Published - Dec 7 1995

Access to Document

10.1016/0960-894X(95)00489-G

Cite this

@article{b32abdb3a98f4d36b416f3c42c061ea2,

title = "Chemoenzymatic synthesis of enantiomers of a new retinoid to investigate the role of chirality in the biological response",

abstract = "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).",

author = "Bruno Charpentier and Bernardon, \{Jean Michel\} and Philippe Diaz and Mich{\`e}le Vion and Corinne Millois and Bruno Bernard and Braham Shroot",

year = "1995",

month = dec,

day = "7",

doi = "10.1016/0960-894X(95)00489-G",

language = "English",

volume = "5",

pages = "2801--2804",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

number = "23",

}

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 - https://www.scopus.com/pages/publications/0028793183

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 -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this