Bacteriochlorophyll

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
CAS Number	17499-98-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:30033;
ChemSpider	21169457 ;
KEGG	C11242;
PubChem CID	11953947;
	InChI 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 [EBI] Key: DSJXIQQMORJERS-AGGZHOMASA-M;
	SMILES 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
Chemical formula	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

Bacteriochlorophylls (BChl) are photosynthetic pigments that occur in various phototrophic bacteria. They were discovered by C. B. van Niel in 1932.^[1] 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^[2]	805, 830–890
BChl b	Purple bacteria	835–850, 1020–1040
BChl c	Green sulfur bacteria, Chloroflexota, C. thermophilum,^[2] 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.)^[3]	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

^ Niel, C. B. (1932). "On the morphology and physiology of the purple and green sulphur bacteria". Archiv für Mikrobiologie. 3: 1–112. doi:10.1007/BF00454965. S2CID 19597530.
^ ^a ^b Bryant DA, et al. (2007-07-27), "Candidatus Chloracidobacterium thermophilum: An Aerobic Phototrophic Acidobacterium", Science, 317 (5837): 523–526, Bibcode:2007Sci...317..523B, doi:10.1126/science.1143236, PMID 17656724, S2CID 20419870
^ Vogl K, et al. (2012-08-10). "Bacteriochlorophyll f: properties of chlorosomes containing the "forbidden chlorophyll"". Front. Microbiol. 3 298: 1–12. doi:10.3389/fmicb.2012.00298. PMC 3415949. PMID 22908012.

[1] Niel, C. B. (1932). "On the morphology and physiology of the purple and green sulphur bacteria". Archiv für Mikrobiologie. 3: 1–112. doi:10.1007/BF00454965. S2CID 19597530.

[Chloracidobacterium-2] Bryant DA, et al. (2007-07-27), "Candidatus Chloracidobacterium thermophilum: An Aerobic Phototrophic Acidobacterium", Science, 317 (5837): 523–526, Bibcode:2007Sci...317..523B, doi:10.1126/science.1143236, PMID 17656724, S2CID 20419870

[3] Vogl K, et al. (2012-08-10). "Bacteriochlorophyll f: properties of chlorosomes containing the "forbidden chlorophyll"". Front. Microbiol. 3 298: 1–12. doi:10.3389/fmicb.2012.00298. PMC 3415949. PMID 22908012.

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