Biosynthesis of porphyrins and related macrocycles. Part 13. Structure of the protoporphyrin isomer derived from coproporphyrinogen IV by the action of beef-liver coproporphyrinogenase: Synthesis of protoporphyrin XIII

Alan R. Battersby; Andrew D. Hamilton; Edward McDonald; Luisa Mombelli; Oi Hoong Wong

doi:10.1039/p19800001283

Biosynthesis of porphyrins and related macrocycles. Part 13. Structure of the protoporphyrin isomer derived from coproporphyrinogen IV by the action of beef-liver coproporphyrinogenase: Synthesis of protoporphyrin XIII

Alan R. Battersby, Andrew D. Hamilton, Edward McDonald, Luisa Mombelli, Oi Hoong Wong

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Coproporphyrinogen IV (8) is synthesised and is oxidatively decarboxylated by coproporphyrinogenase from beef-liver to produce, after aromatisation, a porphyrin proved to be protoporphyrin XIII (11) by spectroscopy and by unambiguous synthesis; the synthetic route is described. A monovinylporphyrin, derived from an intermediate for the conversion (8) → (11), is also isolated. The importance of these results for earlier biosynthetic studies with pyrromethanes is discussed.

Original language	English (US)
Pages (from-to)	1283-1289
Number of pages	7
Journal	Journal of the Chemical Society, Perkin Transactions 1
DOIs	https://doi.org/10.1039/p19800001283
State	Published - 1980

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Battersby, A. R., Hamilton, A. D., McDonald, E., Mombelli, L., & Wong, O. H. (1980). Biosynthesis of porphyrins and related macrocycles. Part 13. Structure of the protoporphyrin isomer derived from coproporphyrinogen IV by the action of beef-liver coproporphyrinogenase: Synthesis of protoporphyrin XIII. Journal of the Chemical Society, Perkin Transactions 1, 1283-1289. https://doi.org/10.1039/p19800001283

Biosynthesis of porphyrins and related macrocycles. Part 13. Structure of the protoporphyrin isomer derived from coproporphyrinogen IV by the action of beef-liver coproporphyrinogenase: Synthesis of protoporphyrin XIII. / Battersby, Alan R.; Hamilton, Andrew D.; McDonald, Edward et al.
In: Journal of the Chemical Society, Perkin Transactions 1, 1980, p. 1283-1289.

Research output: Contribution to journal › Article › peer-review

Battersby, AR, Hamilton, AD, McDonald, E, Mombelli, L & Wong, OH 1980, 'Biosynthesis of porphyrins and related macrocycles. Part 13. Structure of the protoporphyrin isomer derived from coproporphyrinogen IV by the action of beef-liver coproporphyrinogenase: Synthesis of protoporphyrin XIII', Journal of the Chemical Society, Perkin Transactions 1, pp. 1283-1289. https://doi.org/10.1039/p19800001283

Battersby AR, Hamilton AD, McDonald E, Mombelli L, Wong OH. Biosynthesis of porphyrins and related macrocycles. Part 13. Structure of the protoporphyrin isomer derived from coproporphyrinogen IV by the action of beef-liver coproporphyrinogenase: Synthesis of protoporphyrin XIII. Journal of the Chemical Society, Perkin Transactions 1. 1980;1283-1289. doi: 10.1039/p19800001283

Battersby, Alan R. ; Hamilton, Andrew D. ; McDonald, Edward et al. / Biosynthesis of porphyrins and related macrocycles. Part 13. Structure of the protoporphyrin isomer derived from coproporphyrinogen IV by the action of beef-liver coproporphyrinogenase : Synthesis of protoporphyrin XIII. In: Journal of the Chemical Society, Perkin Transactions 1. 1980 ; pp. 1283-1289.

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abstract = "Coproporphyrinogen IV (8) is synthesised and is oxidatively decarboxylated by coproporphyrinogenase from beef-liver to produce, after aromatisation, a porphyrin proved to be protoporphyrin XIII (11) by spectroscopy and by unambiguous synthesis; the synthetic route is described. A monovinylporphyrin, derived from an intermediate for the conversion (8) → (11), is also isolated. The importance of these results for earlier biosynthetic studies with pyrromethanes is discussed.",

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Biosynthesis of porphyrins and related macrocycles. Part 13. Structure of the protoporphyrin isomer derived from coproporphyrinogen IV by the action of beef-liver coproporphyrinogenase: Synthesis of protoporphyrin XIII

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