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 Hamilton, Edward McDonald, Luisa Mombelli, Oi Hoong Wong

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)1283-1289
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
StatePublished - 1980

Fingerprint

Coproporphyrinogen Oxidase
Aromatization
Beef
Biosynthesis
Porphyrins
Isomers
Liver
Spectrum Analysis
Spectroscopy
coproporphyrinogen IV
protoporphyrin IX
Red Meat

ASJC Scopus subject areas

  • Chemistry(all)
  • Medicine(all)

Cite this

@article{5059dd28bbb1488b872a25198e9d2a08,
title = "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",
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.",
author = "Battersby, {Alan R.} and Andrew Hamilton and Edward McDonald and Luisa Mombelli and Wong, {Oi Hoong}",
year = "1980",
language = "English (US)",
pages = "1283--1289",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",
publisher = "Chemical Society",

}

TY - JOUR

T1 - Biosynthesis of porphyrins and related macrocycles. Part 13. Structure of the protoporphyrin isomer derived from coproporphyrinogen IV by the action of beef-liver coproporphyrinogenase

T2 - Synthesis of protoporphyrin XIII

AU - Battersby, Alan R.

AU - Hamilton, Andrew

AU - McDonald, Edward

AU - Mombelli, Luisa

AU - Wong, Oi Hoong

PY - 1980

Y1 - 1980

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0018883143&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0018883143&partnerID=8YFLogxK

M3 - Article

SP - 1283

EP - 1289

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

SN - 1472-7781

ER -