Bacteriochlorophyll

Bacteriochlorophylls (BChl) are photosynthetic pigments that occur in various phototrophic bacteria. They were discovered by C. B. van Niel in 1932. They are related to chlorophylls, which are the primary pigments in plants, algae, and cyanobacteria. Organisms that contain bacteriochlorophyll conduct photosynthesis to sustain their energy requirements, but the process is anoxygenic and does not produce oxygen as a byproduct. They use wavelengths of light not absorbed by plants or cyanobacteria. Replacement of Mg2+ with protons gives bacteriophaeophytin (BPh), the phaeophytin form.

List of major bacteriochlorophylls
Pigment Taxa in vivo infrared absorption maximum (nm)
BChl a Purple bacteria, Heliobacteria, Green Sulfur Bacteria, Chloroflexota, Chloracidobacterium thermophilum 805, 830–890
BChl b Purple bacteria 835–850, 1020–1040
BChl c Green sulfur bacteria, Chloroflexota, C. thermophilum, C. tepidum 745–755
BChl d Green sulfur bacteria 705–740
BChl e Green sulfur bacteria 719–726
BChl f (Discovered by mutation of BChl e synthesis by analogy to BChl c/d. Not evolutionarily favorable.) 700–710
BChl g Heliobacteria 670, 788
  • Structures of major bacteriochlorophylls
  • bacteriochlorophyll a
  • bacteriochlorophyll b
  • bacteriochlorophyll c
  • bacteriochlorophyll d
  • bacteriochlorophyll e
  • bacteriochlorophyll f
  • bacteriochlorophyll g
Bacteriochlorophyll a
Names
IUPAC name
[methyl (3S,4S,13R,14R,21R)-9-acetyl-14-ethyl-4,8,13,18-tetramethyl-20-oxo-3-(3-oxo-3-([(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy)propyl)-13,14-dihydrophorbine-21-carboxylatato(2−)-kappa4N23,N24,N25,N26]magnesium
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C55H75N4O6.Mg/c1-13-39-34(7)41-29-46-48(38(11)60)36(9)43(57-46)27-42-35(8)40(52(58-42)50-51(55(63)64-12)54(62)49-37(10)44(59-53(49)50)28-45(39)56-41)23-24-47(61)65-26-25-33(6)22-16-21-32(5)20-15-19-31(4)18-14-17-30(2)3;/h25,27-32,34-35,39-40,51H,13-24,26H2,1-12H3,(H-,56,57,58,59,60,62);/q-1;+2/p-1/b33-25+;/t31-,32-,34-,35+,39-,40+,51-;/m1./s1 Y[EBI]
    Key: DSJXIQQMORJERS-AGGZHOMASA-M
  • CC[C@@H]1[C@@H](C)C2=N/C/1=C\c3c(C)c4C(=O)[C@H](C(=O)OC)\C\5=C/6\N=C(\C=C\7/N([Mg]n3c45)\C(=C/2)\C(=C7C)C(=O)C)[C@@H](C)[C@@H]6CCC(=O)OC\C=C(/C)\CCC[C@H](C)CCC[C@H](C)CCCC(C)C
Properties
MgC55H74N4O6
Molar mass 911.524 g·mol−1
Appearance Light green to blue-green powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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