title: Stereoselective synthesis of the head group of archaeal phospholipid PGP-Me to investigate bacteriorhodopsin-lipid interactions.
abstract: Phosphatidylglycerophosphate methyl ester (PGP-Me), a major constituent of the archaeal purple membrane, is essential for the proper proton-pump activity of bacteriorhodopsin (bR). We carried out the first synthesis of the bisphosphate head group of PGP-Me using H-phosphonate chemistry that led to the production of a simplified PGP-Me analogue with straight alkyl chains. To investigate the role of this head group in the structural and functional integrity of bR, the analogue was used to reconstitute bR into liposomes, in which bR retained the original trimeric structure and light-induced photocycle activity. Enhanced ordering of an alkyl chain of the (2)H-labelled analogue was observed in (2)H NMR spectra upon interaction with bR. These results together suggest that the bisphosphate moiety plays a role in the proper functioning of bR through the lipid-protein interaction.
authors.affiliation: Department of Chemistry, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan. murata@chem.sci.osaka-u.ac.jp.
authors.forename: Jin
authors.initials: J
authors.lastname: Cui
authors.forename: Satoshi
authors.initials: S
authors.lastname: Kawatake
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Umegawa
authors.forename: Sébastien
authors.initials: S
authors.lastname: Lethu
authors.forename: Masaki
authors.initials: M
authors.lastname: Yamagami
authors.forename: Shigeru
authors.initials: S
authors.lastname: Matsuoka
authors.forename: Fuminori
authors.initials: F
authors.lastname: Sato
authors.forename: Nobuaki
authors.initials: N
authors.lastname: Matsumori
authors.forename: Michio
authors.initials: M
authors.lastname: Murata
mesh_terms: D001436:Bacteriorhodopsins / Q000737:chemistry*; D008968:Molecular Conformation; D010743:Phospholipids / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C407124:PGP-Me; D010743:Phospholipids; D001436:Bacteriorhodopsins