Biosynthesis of unnatural glycolipids possessing diyne moiety in the acyl chain in the green sulfur photosynthetic bacterium Chlorobaculum tepidum grown by supplementation of 10,12-heptadecadiynic acid

•Novel glycolipids possessing a diyne moiety in the acyl chain were biosynthesized.•Supplemental fatty acids were used in the biosynthesis of glycolipids in the photosynthetic bacterium.•The novel glycolipids did not inhibit the formation of photosynthetic antenna complexes.

Unnatural glycolipids possessing the diyne moiety in their acyl groups were successfully biosynthesized in the green sulfur photosynthetic bacterium Chlorobaculum (Cba.) tepidum by cultivation with supplementation of 10,12-heptadecadiynic acid. Monogalactosyldiacylglycerol (MGDG) and rhamnosylgalactosyldiacylglycerol (RGDG) esterified with one 10,12-heptadecadiynic acid were primarily formed in the cells, and small amounts of glycolipids esterified with the two unnatural fatty acids can also be detected. The relative ratio of these unnatural glycolipids occupied in the total glycolipids was estimated to be 49% based on HPLC analysis using a evaporative light scattering detector. These results indicate that the acyl groups in glycolipids, which play important roles in the formation of extramembranous antenna complexes called chlorosomes, can be modified in vivo by cultivation of green sulfur photosynthetic bacteria with exogenous synthetic fatty acids. Visible absorption and circular dichroism spectra of Cba. tepidum containing the unnatural glycolipids demonstrated the formation of chlorosomes, indicating that the unnatural glycolipids in this study did not interfere with the biogenesis of chlorosomes.