Nomenclature of Tetrapyrroles

The recommendations in this version are identical to those in the published document prepared for publication by G. P. Moss (see Eur. J. Biochem., 1988, 178, 277-328; Pure Appl. Chem., 1987, 59, 779-832; Biochemical Nomenclature and Related Documents, 2nd edition, Portland Press, 1992, pages 278-329. Copyright IUBMB and IUPAC]. Footnotes in the printed text have been located as notes after the relevant paragraph or example. Any comments, corrections or suggestions for a future edition should be e-mailed to g.p.moss@qmul.ac.uk. In setting up the World Wide Web version some errors have been detected. The changes have been marked by which is a link to details of the change and where it applies. For problems in converting the text into a World Wide Web version see the IUPAC home page. A PDF of the printed version is available.

Members of Expert Panel: R. Bonnett (UK, Convenor); S. Aronoff (Canada); A. R. Battersby (UK); A. Eschenmoser (Switzerland); H. Falk (Austria); A. Gossauer (Switzerland); H. H. Inhoffen (FRG); A. H. Jackson (UK); D. A. Lightner (USA); S. Onishi (Japan); J. M. Ribo (Spain); C. Rimington (Norway); M. S. Stoll (UK).

Synopsis - In the revised recommendations two new trivial names (isobacteriochlorin and sirohydrochlorin) are defined. Isobacterlochlorin is 2,3,7,8-tetrahydroporphyrin and is isomeric with bacteriochlorin. An example of an isobacteriochlorin is sirohydrochlorin, an intermediate in the biosynthesis of corrinolds. The names of linear tetrapyrroles are amended. The name bilin is now restricted to the fully oxidized parent, and less oxidized forms are named bilane, bilene, and biladiene. Names are now provided for. the analogous dipyrrole system based on the parent dipyrrin. Tables are provided to show the structures of the more commonly encountered compounds using the Fischer system for denoting isomers (the fifteen isomers of mesoporphyrin defined by Fischer, and some isomers of biliverdin). Experience has shown that these names continue to be useful because of their brevity.

Contents

• Preface
• Introduction
• TP-0 General considerations
• TP-1 Fundamental Porphyrin Systems
  • 1.1 Porphyrin ring system
  • 1.2 Numbering
  • 1.3 Additional fused rings
  • 1.4 Skeletal replacement
  • 1.5 Skeletal replacement of nitrogen atom
  • 1.6 Fused porphyrin replacement analogs
  • 1.7 Systematic names for substituted porphyrins
• TP-2 Trivial names and locants for certain substituted porphyrins
  • 2.1 Trivial names and locants
  • 2.2 Roman numeral type notation
• TP-3 Semisystematic porphyrin names
  • 3.1 Semisystematic names in substituted porphyrins
  • 3.2 Subtractive nomenclature
  • 3.3 Combinations of substitutive and subtractive operations
  • 3.4 Additional ring formation
  • 3.5 Skeletal replacement of substituted porphyrins
• TP-4 Reduced porphyrins including chlorins
  • 4.1 Unsubstituted reduced porphyrins
  • 4.2 Substituted reduced porphyrins. Systematic chlorin names
  • 4.3 Substituted reduced porphyrins, and close relatives of the chlorophylls. Trivial names and numbering
  • 4.4 Substituted chlorins. Semisystematic chlorin names
• TP-5 Ring-expanded and ring-contracted systems
  • 5.1 Ring expansion
  • 5.2 Skeletal replacement of ring-expanded systems
  • 5.3 Ring-contracted systems
  • 5.4 Sapphyrin
• TP-6 Linear tetrapyrroles
  • 6.1 Fundamental system
  • 6.2 Unsubstituted oxidised bilanes
  • 6.3 Semisystematic nomenclature
  • 6.4 Trivial names
  • 6.5 Modified trivial names
• TP-7 Relatives of linear tetrapyrroles
  • 7.1 Linear tripyrroles
  • 7.2 Dipyrroles
• TP-8 Metal coordination complexes
  • 8.1 General description
  • 8.2 Coordination nomenclature
  • 8.3 Alternative order of the components of the name
  • 8.4 Trivial names
• TP-9 Metal coordination complexes - less common structural types
  • 9.1 Coordination complexes of unknown structure
  • 9.2 Coordination other than at central nitrogen
  • 9.3 Mononuclear coordination complexes with two tetrapyrrolic ligands
  • 9.4 Porphyrin as a bridging ligand
  • 9.5 Axial bridging ligands
• References
• Appendix 1 Trivially named porphyrins, chlorins, chlorophylls and bilins, fundamental parents
  • A. Trivially Named Porphyrins
  • B. Trivially Named Chlorins
  • B'. Trivially Named Isobacteriochlorins
  • C. Trivially Named Chlorophylls
  • D. Trivially Named Bilanes
  • E. Fundamental Parents
• Appendix 2 Comparison of the numbering of the trivially named porphyrins with numbering based on CNOC/CAS
• Appendix 3 Fischer trivial names
  • A. Porphyrins
  • B. Bilindiones