Isolation and structural determination of C8-vinyl-bacteriochlorophyll d from the bciA and bchU double mutant of the green sulfur bacterium Chlorobaculum tepidum

Photosynth Res. 2014 Jul;121(1):13-23. doi: 10.1007/s11120-014-0007-7. Epub 2014 May 1.


The mutant lacking enzymes BciA and BchU, that catalyzed reduction of the C8-vinyl group and methylation at the C20 position of bacteriochlorophyll (BChl) c, respectively, in the green sulfur bacterium Chlorobaculum tepidum, were constructed. This mutant accumulated C8-vinyl-BChl d derivatives, and a molecular structure of the major pigment was fully characterized by its NMR, mass, and circular dichroism spectra, as well as by chemical modification: (3(1) R)-8-vinyl-12-ethyl-(R[V,E])BChl d was confirmed as a new BChl d species in the cells. In vitro chlorosome-like self-aggregates of this pigment were prepared in an aqueous micellar solution, and formed more rapidly than those of (3(1) R)-8,12-diethyl-(R[E,E])BChl d isolated from the green sulfur bacterium Chlorobaculum parvum NCIB8327d synthesizing BChl d homologs. Their red-shifted Q y absorption bands were almost the same at 761 nm, and the value was larger than those of in vitro self-aggregates of R[E,E]BChl c (737 nm) and R[V,E]BChl c (726 nm), while the monomeric states of the former gave Q y bands at shorter wavelengths than those of the latter. Red shifts by self-aggregation of the two BChl d species were estimated to be 110 nm and much larger than those by BChls c (75 nm for [E,E] and 64 nm for [V,E]).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacteriochlorophylls / chemistry*
  • Chlorobi / genetics
  • Chlorobi / metabolism*
  • Circular Dichroism
  • Magnetic Resonance Spectroscopy
  • Mutation


  • Bacteriochlorophylls
  • bacteriochlorophyll d