Reversed-phase high-performance liquid chromatography and structural assignments of the bacteriochlorophylls-c

Smith, Kevin M.; Craig, Grant; Kehres, Lisa A.; Pfennig, Norbert

doi:10.1016/s0021-9673(01)87879-1

Cited by 51 publications

(33 citation statements)

References 33 publications

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“…For BChl d in most cases two possibilities have to be considered, since BChl d may have either c n 3 o r C2H 5 substituents on C-12 without a correlation with the size of the C-8 substituent (Smith et al 1983a). Fractions 2 and 5, which had clearly different elution times, may represent different stereoisomers of 8-n-propyl-12-ethyl BChl c, although their ratio deviates from that reported for the corresponding pigment in Prosthecochloris aestuarii (Smith et al 1983b). …”

Section: Chlorobium Vibrioformementioning

confidence: 54%

“…The most abundant BChls c in our strain of C. vibrioforme were 8,12-diethyl BChl c and 8-n-propyl-12-ethyl BChl c (53% and 42% of the total BChl c, respectively), while 8-isobutyl BChl c could not be detected. This stands in contrast to Prosthecochloris aestuarii, which contains 8,12-diethyl BChl c and 8-n-propyl-12-ethyl BChl c in a ratio of 3:1 (Smith et al 1983b). However, the stoichiometry of the BChls c that we found resembles fairly well the stoichiometry of the BChls d in C. vibrioforme.…”

Section: Vibrioforme Contained Significant Amountsmentioning

confidence: 74%

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Identification of the major chlorosomal bacteriochlorophylls of the green sulfur bacteria Chlorobium vibrioforme and Chlorobium phaeovibrioides; their function in lateral energy transfer

Otte¹,

Meent

Veelen

et al. 1993

Photosynth Res

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The chlorosomal bacteriochlorophyll (BChl) composition of the green sulfur bacteria Chlorobium vibrioforme and Chlorobium phaeovibrioides was investigated by means of normal-phase high-performance liquid chromatography. From both species a number of homologues was isolated, which were identified by absorption and (252)Cf-plasma desorption mass spectroscopy. Besides BChl d, C. vibrioforme contained a significant amount of BChl c, which may provide an explanation for the previous observation of at least two spectrally different pools of BChl in the chlorosomes of green sulfur bacteria (Otte et al. 1991). C. phaeovibrioides contained various homologues of BChl e only. Absorption spectra in acetone of BChl c, d and e, as well as bacteriopheophytin e are presented. No systematic differences were found for the various homologues of each pigment. In addition to farnesol, the mass spectra revealed the presence of various minor esterifying alcohols in both species, including phytol, oleol, cetol and 4-undecyl-2-furanmethanol, as well as an alcohol of low molecular mass, which is tentatively assumed to be decenol.

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Section: Chlorobium Vibrioformementioning

confidence: 54%

Section: Vibrioforme Contained Significant Amountsmentioning

confidence: 74%

Identification of the major chlorosomal bacteriochlorophylls of the green sulfur bacteria Chlorobium vibrioforme and Chlorobium phaeovibrioides; their function in lateral energy transfer

Otte¹,

Meent

Veelen

et al. 1993

Photosynth Res

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“…Both the R and S epimers at C-3 1 have been identifi ed in BChl c, d, and e from Chlorobium species as well as in BChl c from Cfx. aurantiacus (Smith et al, 1983b;Smith and Simpson, 1986;Fages et al, 1990;Senge and Smith, 1995). In Chlorobium species the ratio of the R and S epimers is highly correlated with the degree of methylation at the C-8 2 and C-12 The Chl.…”

Section: E C-3 1 Hydrationmentioning

confidence: 99%

Bacteriochlorophyll Biosynthesis in Green Bacteria

Frigaard

Chew

Maresca

et al.

Advances in Photosynthesis and Respiration

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“…Hydration at C3 1 is catalyzed by a vinyl hydratase and generates a new chiral center [174,175]. As noted above, both the R and S epimers are present in a given organism and thus the enzyme is not diastereoselective [169,170].…”

Section: Bacteriochlorophylls C D and E (Chlorins)mentioning

confidence: 99%

Chlorophylls, Symmetry, Chirality, and Photosynthesis

et al. 2014

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Chlorophylls are a fundamental class of tetrapyrroles and function as the central reaction center, accessory and photoprotective pigments in photosynthesis. Their unique individual photochemical properties are a consequence of the tetrapyrrole macrocycle, the structural chemistry and coordination behavior of the phytochlorin system, and specific substituent pattern. They achieve their full potential in solar energy conversion by working in concert in highly complex, supramolecular structures such as the reaction centers and light-harvesting complexes of photobiology. The biochemical function of these structures depends on the controlled interplay of structural and functional principles of the apoprotein and pigment cofactors. Chlorophylls and bacteriochlorophylls are optically active molecules with several chiral centers, which are necessary for their natural biological function and the assembly of their supramolecular complexes. However, in many cases the exact role of chromophore stereochemistry in the biological context is unknown. This review gives an overview of chlorophyll research in terms of basic function, biosynthesis and their functional and structural role in photosynthesis. It highlights aspects of chirality and symmetry of chlorophylls to elicit further interest in their role in nature.

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Reversed-phase high-performance liquid chromatography and structural assignments of the bacteriochlorophylls-c

Cited by 51 publications

References 33 publications

Identification of the major chlorosomal bacteriochlorophylls of the green sulfur bacteria Chlorobium vibrioforme and Chlorobium phaeovibrioides; their function in lateral energy transfer

Identification of the major chlorosomal bacteriochlorophylls of the green sulfur bacteria Chlorobium vibrioforme and Chlorobium phaeovibrioides; their function in lateral energy transfer

Bacteriochlorophyll Biosynthesis in Green Bacteria

Chlorophylls, Symmetry, Chirality, and Photosynthesis

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