Stereospecific elimination of hydrogen atoms with opposite absolute orientations during the biosynthesis of orsellinic acid from chiral malonates in Penicillium cyclopium
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 8,p. 646-648
- https://doi.org/10.1039/c39920000646
Abstract
(R)-[1-13C; 2-2H]Malonate and (S)-[1-13C; 2-2H]malonate are transformed, using succinyl-CoA transferase, into their paired chiral malonyl-CoA derivatives; incorporation of the malonyl-CoA derivatives into orsellinic acid is acomplished using homogeneous orsellinic acid synthase from Penicillium cyclopium; mass spectrometric analysis of the orsellinic acid reveals that the hydrogen atoms eliminated from the methylene groups at the 2- and 4-positions of the putative polyketide intermediate are from opposite absolute orientations in malonyl-CoA.Keywords
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