Plant Physiol. Drug Metab Dispos
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Plant Physiology 79:725-729 (1985)
© 1985 American Society of Plant Biologists

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Articles

Intermediates in the Formation of the Chlorophyll Isocyclic Ring 1

Yum-Shing Wong, Paul A. Castelfranco, Dane A. Goff and Kevin M. Smith

Department of Botany, University of California, Davis, California 95616, Department of Chemistry, University of California, Davis, California 95616

Cell-free, organelle-free synthesis of Mg-2,4-divinylpheoporphyrin a5 (MgDVP) from Mg-protoporphyrin IX monomethyl ester (Mg-Proto Me) has been described (Wong and Castelfranco 1984 Plant Physiol 75: 658-661). This system consists of plastid membrane and stromal fractions and requires O2, NAD(P)H and S-adenosylmethionine (SAM). The synthetic 6-methyl-{beta}-ketopropionate analog of Mg-Proto Me was converted to MgDVP by the same catalytic system in the presence of O2 and NADPH. SAM was not required. A compound (X) displaying the kinetic behavior of an intermediate was isolated from reaction mixtures with Mg-Proto Me as the substrate, but not with the 6-methyl-{beta}-ketopropionate analog as the substrate. X was identified as the 6-methyl-{beta}-hydroxypropionate analog of Mg-Proto Me by conversion to the dimethyl ester with CH2N2 and comparison with authentic 6-{beta}-hydroxydimethyl ester. X was converted to MgDVP by the same catalytic system in the presence of O2 and NADPH. We conclude that the conversion of Mg-Proto Me to MgDVP proceeds through the 6-{beta}-hydroxy and the 6-{beta}-ketopropionate esters in agreement with earlier suggestions.

1 Supported by National Science Foundation grants PCM 8108538 (P. A. C.), CHE 8120891 (K. M. S.), and by a University-wide Energy Research Group `seed-money' award.




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