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Title Chirality and structures of bacteriochlorophylls d
Creator/Author Smith, K.M. (Univ. of California, Davis) ; Goff, D.A. ; Fajer, J. ; Barkigia, K.M.
Publication Date1982 Jun 30
OSTI IdentifierOSTI ID: 6720622
DOE Contract NumberAC02-76CH00016
Other Number(s)CODEN: JACSA
Resource TypeJournal Article
Resource RelationJ. Am. Chem. Soc. ; Vol/Issue: 104:13
Subject400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987); ;CHLOROPHYLL-- CHIRALITY;CHLOROPHYLL-- MOLECULAR STRUCTURE; BACTERIA;EXPERIMENTAL DATA;LIQUID COLUMN CHROMATOGRAPHY;NMR SPECTRA;ORGANIC COMPOUNDS
Related SubjectCARBOXYLIC ACIDS;CHROMATOGRAPHY;DATA;HETEROCYCLIC ACIDS;HETEROCYCLIC COMPOUNDS;INFORMATION;MICROORGANISMS;NUMERICAL DATA;ORGANIC ACIDS;ORGANIC COMPOUNDS;ORGANIC NITROGEN COMPOUNDS;PARTICLE PROPERTIES;PHYTOCHROMES;PIGMENTS;PORPHYRINS;SEPARATION PROCESSES;SPECTRA
Description/Abstract Bacteriochlorophylls (BChl) c and d comprise two homologous series of chlorophylls found in the antenna and reaction centers of green sulfur bacteria (Chlorobiacae).^ Despite the continuing controversy concerning the structures of the six BChl c pigments, assignments of the BChl d, which lack the delta methine methyl substituent found in BChl c, have been generally accepted.^ It was recently deduced that the difference between pairs of BChl c lay in the asolute stereochemistry of the chiral 2-(1-hydroxyethyl) substituent; i.e., the bacteriopheophorbide bearing a 4-isobutyl and 5-ethyl was shown to have an S absolute stereochemistry, contrary to assignments of R for the complete mixture of pigments.^ This work reports that the 4-isobutyl-5-ethyl- and 4-isobutyl-5-methylbacteriopheophorbides also possess the 2-(S)-(1-hydroxyethyl) absolute configuration but that the other bacteriopheophorbides d (and presumably BChl d) exhibit the expected R stereochemistry.^ Bchl d were isolated from Chlorobium vibrioforme forma thiosulfatophilum; treatment of the crude chlorophyll extract with methnol and sulfuric acid gave the pheophorbides as an intimate mixture, the gross structures of which had been determined earlier by degradative and synthetic work.^Lengthy high-pressure liquid chromatography work resulted in accumulation of preparative quantities of all six methylbacteriopheophorbides d.^ Nuclear magnetic resonance spectroscopy was used to confirm the configuration of BChl d.
Country of PublicationUnited States
LanguageEnglish
FormatPages: 3747-3749
System Entry Date2001 May 13

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