Bacteriochlorophylls (BChl) are

photosynthetic pigment A photosynthetic pigment (accessory pigment; chloroplast pigment; antenna pigment) is a pigment that is present in chloroplasts or photosynthetic bacteria and captures the light energy necessary for photosynthesis. List of photosynthetic pigmen ...

s that occur in various

phototroph Phototrophs () are organisms that carry out photon capture to produce complex organic compounds (e.g. carbohydrates) and acquire energy. They use the energy from light to carry out various cellular metabolic processes. It is a common misconcep ...

bacteria Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one biological cell. They constitute a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria were among ...

. They were discovered by

C. B. van Niel Cornelis Bernardus van Niel (also known as Kees van Niel) (November 4, 1897 – March 10, 1985) was a Dutch-American microbiologist. He introduced the study of general microbiology to the United States and made key discoveries explaining t ...

in 1932. They are related to

chlorophyll Chlorophyll (also chlorophyl) is any of several related green pigments found in cyanobacteria and in the chloroplasts of algae and plants. Its name is derived from the Greek words , ("pale green") and , ("leaf"). Chlorophyll allow plants to a ...

s, which are the primary pigments in

plant Plants are predominantly photosynthetic eukaryotes of the kingdom Plantae. Historically, the plant kingdom encompassed all living things that were not animals, and included algae and fungi; however, all current definitions of Plantae exclud ...

alga Algae (; singular alga ) is an informal term for a large and diverse group of photosynthetic eukaryotic organisms. It is a polyphyletic grouping that includes species from multiple distinct clades. Included organisms range from unicellular mi ...

e, and

cyanobacteria Cyanobacteria (), also known as Cyanophyta, are a phylum of gram-negative bacteria that obtain energy via photosynthesis. The name ''cyanobacteria'' refers to their color (), which similarly forms the basis of cyanobacteria's common name, blu ...

. Organisms that contain bacteriochlorophyll conduct

photosynthesis Photosynthesis is a process used by plants and other organisms to convert light energy into chemical energy that, through cellular respiration, can later be released to fuel the organism's activities. Some of this chemical energy is stored i ...

to sustain their energy requirements, but do not produce

oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...

as a byproduct. They use wavelengths of light not absorbed by plants or

. Replacement of with protons gives bacteriophaeophytin (BPh), the

phaeophytin Pheophytin or phaeophytin is a chemical compound that serves as the first electron carrier intermediate in the electron transfer pathway of Photosystem II (PS II) in plants, and the type II photosynthetic reaction center (RC P870) found in purpl ...

form. BacterioChlorophyll a.svg, bacteriochlorophyll ''a'' BacterioChlorophyll b.svg, bacteriochlorophyll ''b'' BacterioChlorophyll c.svg, bacteriochlorophyll ''c'' BacterioChlorophyll d.svg, bacteriochlorophyll ''d'' BacterioChlorophyll e.svg, bacteriochlorophyll ''e'' Bacteriochlorophyll f.svg, bacteriochlorophyll ''f'' BacterioChlorophyll g.svg, bacteriochlorophyll ''g''

Structure

Bacteriochlorophylls ''a'', ''b'', and ''g'' are

bacteriochlorin In organic chemistry, chlorins are tetrapyrrole pigments that are partially hydrogenated porphyrins. The parent chlorin is an unstable compound which undergoes air oxidation to porphine. The name chlorin derives from chlorophyll. Chlorophylls a ...

s, meaning their molecules have a bacteriochlorin

macrocycle Macrocycles are often described as molecules and ions containing a ring of twelve or more atoms. Classical examples include the crown ethers, calixarenes, porphyrins, and cyclodextrins. Macrocycles describe a large, mature area of chemistry. ...

ring with two reduced

pyrrole Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4 H4 NH. It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., ''N''-meth ...

rings (B and D). Bacteriochlorophylls ''c'', ''d'', ''e'', and ''f'' are

chlorin In organic chemistry, chlorins are tetrapyrrole pigments that are partially hydrogenated porphyrins. The parent chlorin is an unstable compound which undergoes air oxidation to porphine. The name chlorin derives from chlorophyll. Chlorophylls a ...

s, meaning their molecules have a chlorin

ring with one reduced pyrrole ring (D). Bacteriochlorophylls ''c'' to ''f'' occur in the form of closely related

homologs A couple of homologous chromosomes, or homologs, are a set of one maternal and one paternal chromosome that pair up with each other inside a cell during fertilization. Homologs have the same genes in the same locus (genetics), loci where they pr ...

with different

alkyl group In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloalk ...

s attached to pyrrole rings B and C and are illustrated above in their simplest versions,

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

ified with the

sesquiterpene Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modificatio ...

alcohol

farnesol Farnesol is a natural 15-carbon organic compound which is an acyclic sesquiterpene alcohol. Under standard conditions, it is a colorless liquid. It is hydrophobic, and thus insoluble in water, but miscible with oils. Farnesol is produced from 5- ...

. Bacteriochlorophyll ''g'' has a

vinyl group In organic chemistry, a vinyl group (abbr. Vi; IUPAC name: ethenyl group) is a functional group with the formula . It is the ethylene (IUPAC name: ethene) molecule () with one fewer hydrogen atom. The name is also used for any compound contain ...

in ring (A).

Biosynthesis

There are a large number of known bacteriochlorophylls but all have features in common since the

biosynthetic pathway Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cell ...

involves chlorophyllide ''a'' as an intermediate. Isobacteriochlorins, in contrast, are biosynthesised from

uroporphyrinogen III Uroporphyrinogen III is a tetrapyrrole, the first macrocyclic intermediate in the biosynthesis of heme, chlorophyll, vitamin B12, and siroheme. It is a colorless compound, like other porphyrinogens. Structure The molecular structure of uroporphyri ...

in a separate pathway that leads, for example, to

siroheme Siroheme (or sirohaem) is a heme-like prosthetic group at the active sites of some enzymes to accomplish the six-electron reduction of sulfur and nitrogen. It is a cofactor at the active site of sulfite reductase, which plays a major role in su ...

, cofactor F₄₃₀ and

cobalamin Vitamin B12, also known as cobalamin, is a water-soluble vitamin involved in metabolism. It is one of eight B vitamins. It is required by animals, which use it as a cofactor in DNA synthesis, in both fatty acid and amino acid metabolism. It ...

References

{{photolithotrophic bacteria Photosynthetic pigments Tetrapyrroles de:Chlorophylle#Chemische Struktur bei anoxygenen Phototrophen: Bakteriochlorophylle (Bchl)