Bacteriochlorophyll

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any of the chlorophylls of photosynthetic bacteria. They differ structurally from the chlorophylls of higher plants. Bacteriochlorophylls a to g are known. Bacteriochlorophylls a and b are the best known, being the photosynthetic pigments of purple bacteria. Their purple colour results from the fact that they are reduced in both rings B and D, and thus may be regarded as tetrahydropyrroles. Tetrapyrrole carbon atoms and carbon rings are numbered according to the Fischer and IUPAC systems as indicated below. The structure of bacteriochlorophyll a is shown. Bacteriochlorophyll b has =CH — CH3 in place of the ethyl group on ring B of bacteriochlorophyll a. In some bacteriochlorophylls a the phytyl group may be replaced by a geranylgeranyl group. Bacteriochlorophylls c, d, and e are antenna pigments of Chlorobiaceae, located in chlorobium vesicles (a core structure is shown). These are dihydropyrrole structures, being reduced in ring D only. The esterifying alcohol is farnesol. In these bacteriochlorophylls, the side chain R1 (see core structure) on ring B varies, being ethyl, n-propyl, or isobutyl (in bacteriochlorophyll d neopentyl is also possible). On ring C the side chain R2 is ethyl (in bacteriochlorophyll d methyl is also possible). R3 is methyl in bacteriochlorophylls c and e, and H in bacteriochlorophyll d.









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Bacteriochlorophyll

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Bacteriochlorophyll a. R is phytyl or geranylgeranyl.

Bacteriochlorophylls are photosynthetic pigments that occur in various phototrophic bacteria. They were discovered by Von Neil in 1932 . They are related to chlorophylls, which are the primary pigments in plants, algae, and cyanobacteria. Groups that contain bacteriochlorophyll conduct photosynthesis, but do not produce oxygen. They use wavelengths of light not absorbed by plants or Cyanobacteria. Different groups contain different types of bacteriochlorophyll:

Pigment Bacterial group in vivo infrared absorption maximum (nm)
Bacteriochlorophyll a Purple bacteria (= Proteobacteria), Chloracidobacterium thermophilum[1] 805, 830-890
Bacteriochlorophyll b Purple bacteria 835-850, 1020-1040
Bacteriochlorophyll c Green sulfur bacteria, Chloroflexi, C. thermophilum 745-755
Bacteriochlorophyll cs Chloroflexi 740
Bacteriochlorophyll d Green sulfur bacteria 705-740
Bacteriochlorophyll e Green sulfur bacteria 719-726
Bacteriochlorophyll g Heliobacteria 670, 788

Bacteriochlorophylls a, b, and g are bacteriochlorins, meaning their molecules have a bacteriochlorin macrocycle ring with two reduced pyrrole rings (B and D). Bacteriochlorophylls c, d and e are chlorins, meaning their molecules have a chlorin macrocycle ring with one reduced pyrrole ring (D).

Chemical structures comparing porphin, chlorin, bacteriochlorin, and isobacteriochlorin. Note relocation of C=C double bond between the two bacteriochlorin isomers. There are two π electrons (symbolized by π e-) for every double bond in the macrocycle.

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