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. 1985 Nov;79(3):725–729. doi: 10.1104/pp.79.3.725

Intermediates in the Formation of the Chlorophyll Isocyclic Ring 1

Yum-Shing Wong 1,2, Paul A Castelfranco 1,2, Dane A Goff 1,2, Kevin M Smith 1,2
PMCID: PMC1074960  PMID: 16664481

Abstract

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-β-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-β-ketopropionate analog as the substrate. X was identified as the 6-methyl-β-hydroxypropionate analog of Mg-Proto Me by conversion to the dimethyl ester with CH2N2 and comparison with authentic 6-β-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-β-hydroxy and the 6-β-ketopropionate esters in agreement with earlier suggestions.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Castelfranco P. A., Weinstein J. D., Schwarcz S., Pardo A. D., Wezelman B. E. The Mg insertion step in chlorophyll biosynthesis. Arch Biochem Biophys. 1979 Feb;192(2):592–598. doi: 10.1016/0003-9861(79)90130-9. [DOI] [PubMed] [Google Scholar]
  2. Chereskin B. M., Castelfranco P. A. Effects of Iron and Oxygen on Chlorophyll Biosynthesis : II. OBSERVATIONS ON THE BIOSYNTHETIC PATHWAY IN ISOLATED ETIOCHLOROPLASTS. Plant Physiol. 1982 Jan;69(1):112–116. doi: 10.1104/pp.69.1.112. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Chereskin B. M., Wong Y. S., Castelfranco P. A. In Vitro Synthesis of the Chlorophyll Isocyclic Ring : Transformation of Magnesium-Protoporphyrin IX and Magnesium-Protoporphyrin IX Monomethyl Ester into Magnesium-2,4-Divinyl Pheoporphyrin A(5). Plant Physiol. 1982 Oct;70(4):987–993. doi: 10.1104/pp.70.4.987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Cox M. T., Jackson A. H., Kenner G. W., McCombie S. W., Smith K. M. Pyrroles and related compounds. 29. Vinylporphyrin beta-keto-esters. J Chem Soc Perkin 1. 1974;4:516–527. [PubMed] [Google Scholar]
  5. Ellsworth R. K., Aronoff S. Investigations of the biogenesis of chlorophyll a. IV. Isolation and partial characterization of some biosynthetic intermediates between Mg-protoporphine IX monomethyl ester and Mg-vinylpheoporphine a5, obtained from Chlorella mutants. Arch Biochem Biophys. 1969 Mar;130(1):374–383. doi: 10.1016/0003-9861(69)90047-2. [DOI] [PubMed] [Google Scholar]
  6. Ellsworth R. K., Aronoff S. Investigations on the biogenesis of chlorophyll a. 3. Biosynthesis of Mg-vinylpheoporphine a5 methylester from Mg-protoporphine IX monomethylester as observed in Chlorella mutants. Arch Biochem Biophys. 1968 Apr;125(1):269–277. doi: 10.1016/0003-9861(68)90661-9. [DOI] [PubMed] [Google Scholar]
  7. Fuesler T. P., Hanamoto C. M., Castelfranco P. A. Separation of Mg-Protoporphyrin IX and Mg-Protoporphyrin IX Monomethyl Ester Synthesized de novo by Developing Cucumber Etioplasts. Plant Physiol. 1982 Feb;69(2):421–423. doi: 10.1104/pp.69.2.421. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. GRANICK S. The structural and functional relationships between heme and chlorophyll. Harvey Lect. 1948 1949;Series 44:220–245. [PubMed] [Google Scholar]
  9. Hardy S. I., Castelfranco P. A., Rebeiz C. A. Effect of the hypocotyl hook on greening in etiolated cucumber cotyledons. Plant Physiol. 1970 Nov;46(5):705–707. doi: 10.1104/pp.46.5.705. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Rebeiz C. A., Mattheis J. R., Smith B. B., Rebeiz C., Dayton D. F. Chloroplast biogenesis. Biosynthesis and accumulation of Mg-protoprophyrin IX monoester and longer wavelength metalloporphyrins by greening cotyledons. Arch Biochem Biophys. 1975 Feb;166(2):446–465. doi: 10.1016/0003-9861(75)90408-7. [DOI] [PubMed] [Google Scholar]
  11. Smith B. B., Rebeiz C. A. Chloroplast biogenesis: detection of Mg-protoporphyrin chelatase in vitro. Arch Biochem Biophys. 1977 Apr 15;180(1):178–185. doi: 10.1016/0003-9861(77)90023-6. [DOI] [PubMed] [Google Scholar]
  12. Wong Y. S., Castelfranco P. A. Properties of the Mg-Protoporphyrin IX Monomethyl Ester (Oxidative) Cyclase System. Plant Physiol. 1985 Nov;79(3):730–733. doi: 10.1104/pp.79.3.730. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Wong Y. S., Castelfranco P. A. Resolution and Reconstitution of Mg-Protoporphyrin IX Monomethyl Ester (Oxidative) Cyclase, the Enzyme System Responsible for the Formation of the Chlorophyll Isocyclic Ring. Plant Physiol. 1984 Jul;75(3):658–661. doi: 10.1104/pp.75.3.658. [DOI] [PMC free article] [PubMed] [Google Scholar]

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