Stereoselective aliphatic hydroxylation of 6‐n‐propylchromone‐2‐carboxylic acid by female Dutch rabbits
作者:
Steven M. Winter,
John Caldwell,
期刊:
Chirality
(WILEY Available online 1992)
卷期:
Volume 4,
issue 1
页码: 1-7
ISSN:0899-0042
年代: 1992
DOI:10.1002/chir.530040103
出版商: Alan R. Liss, Inc.
关键词: product enantioselectivity;aliphatic hydroxylation;6‐n‐propylchromone carboxylic acid;chiral HPLC;chiral shift1H‐NMR
数据来源: WILEY
摘要:
Abstract6‐n‐Alkylchromone‐2‐carboxylic acids are metabolized solely by aliphatic oxidation. In the rabbit, the 6‐n‐propyl congener (PCCA) undergoes ω‐1 hydroxylation exclusively. Following administration of PCCA to female Dutch rabbits (500 μmol/kg), some 77% of the dose was excreted in the urine, 41% as PCCA and 36% as 6‐(2'‐hydroxy‐n‐propyl)chromone‐2‐carboxylic acid. Since this metabolite is chiral, we have examined the stereochemistry of the excreted material. Diastereoisomeric (as camphanate and α‐methoxy‐α‐(trifluoromethyl)phenylacetate esters) and direct chiral HPLC and chiral lanthanide shift NMR have each shown the S:R ratio of the excreted metabolite to be 76:24. When rabbits were dosed with the racemic metabolite, excretion of the compound was not stereoselective. The regio‐ and stereo‐selectivity of the aliphatic hydroxylation of PCCA are thus reflections of the selectivities of the enzyme systems responsible for its formation and suggest PCCA to be an appropriate probe compound for the s
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