Article,
Fungal biosynthesis of 3-nitropropanoic acid
J. Chem. Soc., Perkin Trans. 1, (1992)
Abstract
The origin of 3-nitropropanoic acid 1 in the fungus Penicillium atrovenetum
has been examined using a combination of stable isotope methods.
The incorporation of 13C and 15N from DL-2-13C, 15Naspartic acid
2a,18O from 18O2,15N from DL-diethyl 15N nitrosuccinate 6 and
2H from L-2,3,3-2H3aspartate, DL-4-13C, 2,3,3-2H3aspartate and
from (2S,3R)-3-2H- and (2S,3S)-2,3-2H2-aspartates indicate a
biosynthetic pathway L-aspartate 2(S)-nitrosuccinate 51. Mature
cells of P. atrovenetum which produce 3-nitropropanoate dehydrogenase
catalyse an apparent futile cycle between 1 and 3-nitroacrylate
3 with loss of the stereospecific integrity of the hydrogen at the
2-position of 1.
