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Biosynthesis of porphyrins and related macrocycles. Part 45. Determination by a novel X-ray method of the absolute configuration of the spiro lactam which inhibits uroporphyrinogen III synthase (cosynthetase)

DOI: 10.1039/p19960002091

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2091 - 2102 (1996)

Update date:2022-08-03

Topics:

Authors:

Spivey, Alan C.Spivey, Alan C.

Capretta, AlfredoCapretta, Alfredo

Frampton, Christopher S.Frampton, Christopher S.

Leeper, Finian J.Leeper, Finian J.

Battersby, Alan R.Battersby, Alan R.

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Article abstract of DOI:10.1039/p19960002091

A novel approach, involving X-ray analysis of a specifically designed racemate, in combination with correlations by circular dichroism, allows the absolute configuration of the spiro lactam 4 to be determined. The outcome is that the enantiomer of this lactam which strongly inhibits uroporphyrinogen III synthase (cosynthetase) has the R-configuration and the implications of this finding are briefly discussed.

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Product name:(S)-3-[(3R,4R,5R)-4,5-((R)-Benzylidenedioxy)-2-oxotetrahydropyran-3-yloxycarbonylmethyl]-9-benzyloxycarbonyl-2,7-bis(2-methoxycarbonylethyl)-8-methoxycarbonylmethyl-4-methyl-4,5-dihydrodipyrrin-1(10H)-one

Cas No:183061-70-3

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