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Protoporphyrin IX

April 10, 2024

Protoporphyrin IX is an organic compound, classified as a porphyrin, that plays an important role in living organisms as a precursor to other critical compounds like heme (hemoglobin) and chlorophyll. It is a deeply colored solid that is not soluble in water. The name is often abbreviated as PPIX.

Protoporphyrin IX
Identifiers
  • 553-12-8 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:15430 Y
ChEMBL
  • ChEMBL267548 Y
ChemSpider
  • 10469486 Y
ECHA InfoCard 100.008.213
EC Number
  • 209-033-7
251232
KEGG
  • C02191
  • 4971
UNII
  • C2K325S808 Y
  • DTXSID4048353
  • InChI=1S/C34H34N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16- Y
    Key: KSFOVUSSGSKXFI-UJJXFSCMSA-N Y
  • CC\1=C(/C/2=C/C3=N/C(=C\C4=C(C(=C(N4)/C=C\5/C(=C(C(=N5)/C=C1\N2)C=C)C)C=C)C)/C(=C3CCC(=O)O)C)CCC(=O)O
Properties
C34H34N4O4
Molar mass 562.658 g/mol
Density 1.27 g/cm3
Hazards
GHS labelling:[1]
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Protoporphyrin IX contains a porphine core, a tetrapyrrole macrocycle with a marked aromatic character. Protoporphyrin IX is essentially planar, except for the N-H bonds that are bent out of the plane of the rings, in opposite (trans) directions.[2]

Nomenclature edit

The general term protoporphyrin refers to porphine derivatives that have the outer hydrogen atoms in the four pyrrole rings replaced by other functional groups. The prefix proto often means 'first' in science nomenclature (such as carbon protoxide), hence Hans Fischer is thought to have coined the name protoporphyrin as the first class of porphyrins.[3] Fischer described iron-deprived heme becoming the "proto-" porphyrin, particularly in reference to Hugo Kammerer's porphyrin.[4][5] In modern times, 'proto-' specifies a porphyrin species bearing methyl, vinyl, and carboxyethyl/propionate side groups.[6]

Fischer also generated the Roman numeral naming system which includes 15 protoporphyrin analogs, the naming system is not systematic however.[7] An alternative name for heme is iron protoporphyrin IX (iron PPIX). PPIX contains four methyl groups −CH3 (M), two vinyl groups −CH=CH2 (V), and two propionic acid groups −CH2−CH2−COOH (P). The suffix "IX" indicates that these chains occur in the circular order MV-MV-MP-PM around the outer cycle at the following respective positions: c2,c3-c7,c8-c12,c13-c17,c18.[7]

The methine bridges of PPIX are named alpha (c5), beta (c10), gamma (c15), and delta (c20). In the context of heme, metabolic biotransformation by heme oxygenase results in the selective opening of the alpha-methine bridge to form biliverdin/bilirubin. In this case, the resulting bilin carries the suffix IXα which indicates the parent molecule was protoporphyrin IX cleaved at the alpha position. Non-enzymatic oxidation may result in the ring opening at other bridge positions.[8] The use of Greek letters in this context originates from the pioneering work of Georg Barkan in 1932.[9]

Properties edit

  • When UV light is shone on the compound, it fluoresces with a bright red color.
  • It Is also the component in egg shells that give them their characteristic brown color.[10]

Natural occurrence edit

The compound is encountered in nature in the form of complexes where the two inner hydrogen atoms are replaced by a divalent metal cation. When complexed with an iron(II) (ferrous) cation Fe2+, the molecule is called heme. Hemes are prosthetic groups in some important proteins. These heme-containing proteins include hemoglobin, myoglobin, and cytochrome c. Complexes can also be formed with other metal ions, such as zinc.[11]

Biosynthesis edit

Main article: Porphyrin § Synthesis

The compound is synthesized from acyclic precursors via a mono-pyrrole (porphobilinogen) then a tetrapyrrole (a porphyrinogen, specifically uroporphyrinogen III). This precursor is converted to protoporphyrinogen IX, which is oxidized to protoporphyrin IX.[11] The last step is mediated by the enzyme protoporphyrinogen oxidase.

 

Protoporphyrin IX is an important precursor to biologically essential prosthetic groups such as heme, cytochrome c, and chlorophylls. As a result, a number of organisms are able to synthesize this tetrapyrrole from basic precursors such as glycine and succinyl-CoA, or glutamic acid. Despite the wide range of organisms that synthesize protoporphyrin IX, the process is largely conserved from bacteria to mammals with a few distinct exceptions in higher plants.[12][13][14]

In the biosynthesis of those molecules, the metal cation is inserted into protoporphyrin IX by enzymes called chelatases. For example, ferrochelatase converts the compound into heme B (i.e. Fe-protoporphyrin IX or protoheme IX). In chlorophyll biosynthesis, the enzyme magnesium chelatase converts it into Mg-protoporphyrin IX.

Described metalloprotoporphyrin IX derivatives edit

Protoporphyrin IX reacts with iron salts in air to give the complex FeCl(PPIX).[15] Heme coordinated with chlorine is known as hemin. Many metals other than Fe form Heme-like complexes when coordinated to PPIX. Of particular interest are cobalt derivatives because they also function as oxygen carriers.[16] Other metals - nickel, tin, chromium - have been investigated for their therapeutic value.[17]

Palepron is the disodium salt of protoporphyrin IX.[18]

History edit

Laidlaw may have first isolated PPIX in 1904.[5]

See also edit

References edit

  1. ^ "protoporphyrin IX". pubchem.ncbi.nlm.nih.gov.
  2. ^ Winslow S. Caughey; James A. Ibers (1977). "Crystal and Molecular Structure of the Free Base Porphyrin, Protoporphyrin IX Dimethyl Ester". J. Am. Chem. Soc. 99 (20): 6639–6645. doi:10.1021/ja00462a027. PMID 19518.
  3. ^ Vicente, Maria da G.H.; Smith, Kevin M. (2014). "Syntheses and Functionalizations of Porphyrin Macrocycles". Current Organic Synthesis. 11 (1): 3–28. doi:10.2174/15701794113106660083. ISSN 1570-1794. PMC 4251786. PMID 25484638.
  4. ^ Fischer, Hans (1930). "On haemin and the relationships between haemin and chlorophyll" (PDF). Nobel Prize.
  5. ^ a b With, Torben K. (1980-01-01). "A short history of porphyrins and the porphyrias". International Journal of Biochemistry. 11 (3–4): 189–200. doi:10.1016/0020-711X(80)90219-0. ISSN 0020-711X. PMID 6993245.
  6. ^ Neves, Ana Carolina de Oliveira; Galván, Ismael (2020). "Models for human porphyrias: Have animals in the wild been overlooked?". BioEssays. 42 (12): 2000155. doi:10.1002/bies.202000155. ISSN 1521-1878. PMID 33155299. S2CID 226269267.
  7. ^ a b Moss, G. P. (1988-12-15). "Nomenclature of tetrapyrroles. Recommendations 1986 IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN)". European Journal of Biochemistry. 178 (2): 277–328. doi:10.1111/j.1432-1033.1988.tb14453.x. ISSN 0014-2956. PMID 3208761.
  8. ^ Berk, Paul D.; Berlin, Nathaniel I. (1977). International Symposium on Chemistry and Physiology of Bile Pigments. U.S. Department of Health, Education, and Welfare, Public Health Service, National Institutes of Health.
  9. ^ Barkan, Georg; Schales, Otto (1938). "A Hæmoglobin from Bile Pigment". Nature. 142 (3601): 836–837. Bibcode:1938Natur.142..836B. doi:10.1038/142836b0. ISSN 1476-4687. S2CID 4073510.
  10. ^ Sachar, M.; Anderson, K. E.; Ma, X. (2016). "Protoporphyrin IX: The Good, the Bad, and the Ugly". Journal of Pharmacology and Experimental Therapeutics. 356 (2): 267–275. doi:10.1124/jpet.115.228130. PMC 4727154. PMID 26588930.
  11. ^ a b Paul R. Ortiz de Montellano (2008). "Hemes in Biology". Wiley Encyclopedia of Chemical Biology. John Wiley & Sons. pp. 1–10. doi:10.1002/9780470048672.wecb221. ISBN 978-0-470-04867-2.
  12. ^ A. R. Battersby; C. J. R. Fookes; G. W. J. Matcham; E. McDonald (1980). "Biosynthesis of the pigments of life: formation of the macrocycle". Nature. 285 (5759): 17–21. Bibcode:1980Natur.285...17B. doi:10.1038/285017a0. PMID 6769048. S2CID 9070849.
  13. ^ F. J. Leeper (1983). "The biosynthesis of porphyrins, chlorophylls, and vitamin B12". Natural Product Reports. 2 (1): 19–47. doi:10.1039/NP9850200019. PMID 3895052.
  14. ^ G. Layer; J. Reichelt; D. Jahn; D. W. Heinz (2010). "Structure and function of enzymes in heme biosynthesis". Protein Science. 19 (6): 1137–1161. doi:10.1002/pro.405. PMC 2895239. PMID 20506125.
  15. ^ Chang, C. K.; DiNello, R. K.; Dolphin, D. (2007). "Iron Porphines". Inorganic Syntheses. Vol. 20. pp. 147–155. doi:10.1002/9780470132517.ch35. ISBN 978-0-470-13251-7. {{cite book}}: |journal= ignored (help)
  16. ^ Dias, Sı́Lvio L.P; Gushikem, Yoshitaka; Ribeiro, Emerson S.; Benvenutti, Edilson V. (2002). "Cobalt(II) hematoporphyrin IX and protoporphyrin IX complexes immobilized on highly dispersed titanium(IV) oxide on a cellulose microfiber surface: Electrochemical properties and dissolved oxygen reduction study". Journal of Electroanalytical Chemistry. 523 (1–2): 64–69. doi:10.1016/S0022-0728(02)00722-2.
  17. ^ Verman, Hendrik J.; Ekstrand, Bradley C.; Stevenson, David K. (1993). "Selection of Metalloporphyrin Heme Oxygenase Inhibitors Based on Potency and Photoreactivity". Pediatric Research. 33 (2): 195–200. doi:10.1203/00006450-199302000-00021. PMID 8433895. S2CID 9223457.
  18. ^ PubChem. "Protoporphyrin disodium". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-04-15.

April 10, 2024
protoporphyrin, organic, compound, classified, porphyrin, that, plays, important, role, living, organisms, precursor, other, critical, compounds, like, heme, hemoglobin, chlorophyll, deeply, colored, solid, that, soluble, water, name, often, abbreviated, ppix,. Protoporphyrin IX is an organic compound classified as a porphyrin that plays an important role in living organisms as a precursor to other critical compounds like heme hemoglobin and chlorophyll It is a deeply colored solid that is not soluble in water The name is often abbreviated as PPIX Protoporphyrin IX IdentifiersCAS Number 553 12 8 Y3D model JSmol Interactive imageChEBI CHEBI 15430 YChEMBL ChEMBL267548 YChemSpider 10469486 YECHA InfoCard 100 008 213EC Number 209 033 7Gmelin Reference 251232KEGG C02191PubChem CID 4971UNII C2K325S808 YCompTox Dashboard EPA DTXSID4048353InChI InChI 1S C34H34N4O4 c1 7 21 17 3 25 13 26 19 5 23 9 11 33 39 40 31 37 26 16 32 24 10 12 34 41 42 20 6 28 38 32 15 30 22 8 2 18 4 27 36 30 14 29 21 35 25 h7 8 13 16 35 38H 1 2 9 12H2 3 6H3 H 39 40 H 41 42 b25 13 26 13 27 14 28 15 29 14 30 15 31 16 32 16 YKey KSFOVUSSGSKXFI UJJXFSCMSA N YSMILES CC 1 C C 2 C C3 N C C C4 C C C N4 C C 5 C C C N5 C C1 N2 C C C C C C C C3CCC O O C CCC O OPropertiesChemical formula C34H34N4O4Molar mass 562 658 g molDensity 1 27 g cm3HazardsGHS labelling 1 PictogramsSignal word WarningHazard statements H315 H319 H335Precautionary statements P261 P264 P264 P265 P271 P280 P302 P352 P304 P340 P305 P351 P338 P319 P321 P332 P317 P337 P317 P362 P364 P403 P233 P405 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Protoporphyrin IX contains a porphine core a tetrapyrrole macrocycle with a marked aromatic character Protoporphyrin IX is essentially planar except for the N H bonds that are bent out of the plane of the rings in opposite trans directions 2 Contents 1 Nomenclature 2 Properties 3 Natural occurrence 4 Biosynthesis 5 Described metalloprotoporphyrin IX derivatives 6 History 7 See also 8 ReferencesNomenclature editThe general term protoporphyrin refers to porphine derivatives that have the outer hydrogen atoms in the four pyrrole rings replaced by other functional groups The prefix proto often means first in science nomenclature such as carbon protoxide hence Hans Fischer is thought to have coined the name protoporphyrin as the first class of porphyrins 3 Fischer described iron deprived heme becoming the proto porphyrin particularly in reference to Hugo Kammerer s porphyrin 4 5 In modern times proto specifies a porphyrin species bearing methyl vinyl and carboxyethyl propionate side groups 6 Fischer also generated the Roman numeral naming system which includes 15 protoporphyrin analogs the naming system is not systematic however 7 An alternative name for heme is iron protoporphyrin IX iron PPIX PPIX contains four methyl groups CH3 M two vinyl groups CH CH2 V and two propionic acid groups CH2 CH2 COOH P The suffix IX indicates that these chains occur in the circular order MV MV MP PM around the outer cycle at the following respective positions c2 c3 c7 c8 c12 c13 c17 c18 7 The methine bridges of PPIX are named alpha c5 beta c10 gamma c15 and delta c20 In the context of heme metabolic biotransformation by heme oxygenase results in the selective opening of the alpha methine bridge to form biliverdin bilirubin In this case the resulting bilin carries the suffix IXa which indicates the parent molecule was protoporphyrin IX cleaved at the alpha position Non enzymatic oxidation may result in the ring opening at other bridge positions 8 The use of Greek letters in this context originates from the pioneering work of Georg Barkan in 1932 9 Properties editWhen UV light is shone on the compound it fluoresces with a bright red color It Is also the component in egg shells that give them their characteristic brown color 10 Natural occurrence editThe compound is encountered in nature in the form of complexes where the two inner hydrogen atoms are replaced by a divalent metal cation When complexed with an iron II ferrous cation Fe2 the molecule is called heme Hemes are prosthetic groups in some important proteins These heme containing proteins include hemoglobin myoglobin and cytochrome c Complexes can also be formed with other metal ions such as zinc 11 Biosynthesis editMain article Porphyrin Synthesis The compound is synthesized from acyclic precursors via a mono pyrrole porphobilinogen then a tetrapyrrole a porphyrinogen specifically uroporphyrinogen III This precursor is converted to protoporphyrinogen IX which is oxidized to protoporphyrin IX 11 The last step is mediated by the enzyme protoporphyrinogen oxidase nbsp Protoporphyrin IX is an important precursor to biologically essential prosthetic groups such as heme cytochrome c and chlorophylls As a result a number of organisms are able to synthesize this tetrapyrrole from basic precursors such as glycine and succinyl CoA or glutamic acid Despite the wide range of organisms that synthesize protoporphyrin IX the process is largely conserved from bacteria to mammals with a few distinct exceptions in higher plants 12 13 14 In the biosynthesis of those molecules the metal cation is inserted into protoporphyrin IX by enzymes called chelatases For example ferrochelatase converts the compound into heme B i e Fe protoporphyrin IX or protoheme IX In chlorophyll biosynthesis the enzyme magnesium chelatase converts it into Mg protoporphyrin IX Described metalloprotoporphyrin IX derivatives editProtoporphyrin IX reacts with iron salts in air to give the complex FeCl PPIX 15 Heme coordinated with chlorine is known as hemin Many metals other than Fe form Heme like complexes when coordinated to PPIX Of particular interest are cobalt derivatives because they also function as oxygen carriers 16 Other metals nickel tin chromium have been investigated for their therapeutic value 17 Palepron is the disodium salt of protoporphyrin IX 18 History editLaidlaw may have first isolated PPIX in 1904 5 See also editCarbon monoxide releasing molecules Heme oxygenase Biosynthesis of chlorophylls Biosynthesis of hemesReferences edit protoporphyrin IX pubchem ncbi nlm nih gov Winslow S Caughey James A Ibers 1977 Crystal and Molecular Structure of the Free Base Porphyrin Protoporphyrin IX Dimethyl Ester J Am Chem Soc 99 20 6639 6645 doi 10 1021 ja00462a027 PMID 19518 Vicente Maria da G H Smith Kevin M 2014 Syntheses and Functionalizations of Porphyrin Macrocycles Current Organic Synthesis 11 1 3 28 doi 10 2174 15701794113106660083 ISSN 1570 1794 PMC 4251786 PMID 25484638 Fischer Hans 1930 On haemin and the relationships between haemin and chlorophyll PDF Nobel Prize a b With Torben K 1980 01 01 A short history of porphyrins and the porphyrias International Journal of Biochemistry 11 3 4 189 200 doi 10 1016 0020 711X 80 90219 0 ISSN 0020 711X PMID 6993245 Neves Ana Carolina de Oliveira Galvan Ismael 2020 Models for human porphyrias Have animals in the wild been overlooked BioEssays 42 12 2000155 doi 10 1002 bies 202000155 ISSN 1521 1878 PMID 33155299 S2CID 226269267 a b Moss G P 1988 12 15 Nomenclature of tetrapyrroles Recommendations 1986 IUPAC IUB Joint Commission on Biochemical Nomenclature JCBN European Journal of Biochemistry 178 2 277 328 doi 10 1111 j 1432 1033 1988 tb14453 x ISSN 0014 2956 PMID 3208761 Berk Paul D Berlin Nathaniel I 1977 International Symposium on Chemistry and Physiology of Bile Pigments U S Department of Health Education and Welfare Public Health Service National Institutes of Health Barkan Georg Schales Otto 1938 A Haemoglobin from Bile Pigment Nature 142 3601 836 837 Bibcode 1938Natur 142 836B doi 10 1038 142836b0 ISSN 1476 4687 S2CID 4073510 Sachar M Anderson K E Ma X 2016 Protoporphyrin IX The Good the Bad and the Ugly Journal of Pharmacology and Experimental Therapeutics 356 2 267 275 doi 10 1124 jpet 115 228130 PMC 4727154 PMID 26588930 a b Paul R Ortiz de Montellano 2008 Hemes in Biology Wiley Encyclopedia of Chemical Biology John Wiley amp Sons pp 1 10 doi 10 1002 9780470048672 wecb221 ISBN 978 0 470 04867 2 A R Battersby C J R Fookes G W J Matcham E McDonald 1980 Biosynthesis of the pigments of life formation of the macrocycle Nature 285 5759 17 21 Bibcode 1980Natur 285 17B doi 10 1038 285017a0 PMID 6769048 S2CID 9070849 F J Leeper 1983 The biosynthesis of porphyrins chlorophylls and vitamin B12 Natural Product Reports 2 1 19 47 doi 10 1039 NP9850200019 PMID 3895052 G Layer J Reichelt D Jahn D W Heinz 2010 Structure and function of enzymes in heme biosynthesis Protein Science 19 6 1137 1161 doi 10 1002 pro 405 PMC 2895239 PMID 20506125 Chang C K DiNello R K Dolphin D 2007 Iron Porphines Inorganic Syntheses Vol 20 pp 147 155 doi 10 1002 9780470132517 ch35 ISBN 978 0 470 13251 7 a href Template Cite book html title Template Cite book cite book a journal ignored help Dias Si Lvio L P Gushikem Yoshitaka Ribeiro Emerson S Benvenutti Edilson V 2002 Cobalt II hematoporphyrin IX and protoporphyrin IX complexes immobilized on highly dispersed titanium IV oxide on a cellulose microfiber surface Electrochemical properties and dissolved oxygen reduction study Journal of Electroanalytical Chemistry 523 1 2 64 69 doi 10 1016 S0022 0728 02 00722 2 Verman Hendrik J Ekstrand Bradley C Stevenson David K 1993 Selection of Metalloporphyrin Heme Oxygenase Inhibitors Based on Potency and Photoreactivity Pediatric Research 33 2 195 200 doi 10 1203 00006450 199302000 00021 PMID 8433895 S2CID 9223457 PubChem Protoporphyrin disodium pubchem ncbi nlm nih gov Retrieved 2021 04 15 Retrieved from https en wikipedia org w index php title Protoporphyrin IX amp oldid 1188972361, wikipedia, wiki, book, books, library,

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