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Cyclopropane-ring formation in the acyl groups of chlorosome glycolipids is crucial for acid resistance of green bacterial antenna systems.

Abstract：

:Green photosynthetic bacteria have unique light-harvesting antenna systems called chlorosomes. Chlorobaculum tepidum, a model organism of the bacteria, biosynthesized monogalactosyl- and rhamnosylgalactosyldiacylglycerides possessing a methylene-bridged palmitoleyl group characterized by a cis-substituted cyclopropane ring as the dominant glycolipids of its chlorosome surface. The formation of the cyclopropane ring was chemically inhibited by supplementation of sinefungin, an analog of S-adenosyl-L-methionine, into the bacterial cultivation. The presence of the cyclopropane ring reinforced acid resistance of the light-harvesting chlorosomes and suppressed acidic demetalation (pheophytinization) of bacteriochlorophyll-c pigments constructing the core part of chlorosomes. The ring-formation would represent direct and post-synthetic modifications of chlorosome membrane properties and was tolerant of acidic environments.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Mizoguchi T,Tsukatani Y,Harada J,Takasaki S,Yoshitomi T,Tamiaki H

doi

10.1016/j.bmc.2013.04.030

subject

Has Abstract

pub_date

2013-07-01 00:00:00

pages

3689-94

issue

13

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(13)00356-8

journal_volume

21

pub_type

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