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Determination of Stereochemistry of Bacteriochlorophyll gF and 81-Hydroxy-chlorophyll aF from Heliobacterium modesticaldum

Authors

  • Tadashi Mizoguchi,

    1. Department of Bioscience and Biotechnology, Faculty of Science and Engineering, Ritsumeikan University, Kusatsu 525–8577, Japan
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  • Hirozo Oh-oka,

    1. Department of Biology, Graduate School of Science, Osaka University, Toyonaka 560-0043, Japan
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  • Hitoshi Tamiaki

    Corresponding author
    1. Department of Bioscience and Biotechnology, Faculty of Science and Engineering, Ritsumeikan University, Kusatsu 525–8577, Japan
      *To whom correspondence should be addressed: Department of Bioscience and Biotechnology, Faculty of Science and Engineering, Ritsumeikan University, Kusatsu, Shiga 525–8577, Japan. Fax: +81-77-561-2659; e-mail: tamiaki@se.ritsumei.ac.jp
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  • Posted on the website on 3 March 2005

*To whom correspondence should be addressed: Department of Bioscience and Biotechnology, Faculty of Science and Engineering, Ritsumeikan University, Kusatsu, Shiga 525–8577, Japan. Fax: +81-77-561-2659; e-mail: tamiaki@se.ritsumei.ac.jp

ABSTRACT

The reaction center complex of heliobacteria contains three kinds of chlorophyll pigments, bacteriochlorophyll gF (BChl gF), its 132-epimer BChl gF and 81-hydroxy-chlorophyll aF (81-OH-Chl aF). Because the full stereochemistry of these naturally occurring chlorophyllous pigments has remained unknown, we determined the stereochemistry of both BChl gF and 81-OH-Chl aF extracted from Heliobacterium modesticaldum. The configurations of the specific functional groups at ring-B as well as those at ring-D and -E were investigated by use of nuclear Overhauser effect correlations in their 1H-NMR spectra and circular dichroism spectra, as well as by modified Mosher's method in their chemical modification: (1) E-configuration was confirmed for the 8-ethylidene group at ring-B in BChl gF, (2) R-configuration was identified for the 1-hydroxyethyl group at ring-B in 81-OH-Chl aF and (3) 132-(R)-, 17-(S)- and 18-(S)-configurations at ring-D and -E in both BChl gF and 81-OH-Chl aF were confirmed. These stereo-chemistries enabled us to discuss their biosynthesis and to propose possible routes for preparation of ethylidene and 1-hydroxyethyl groups at the 8-position.

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