Stereoselective synthesis of the head group of archaeal phospholipid PGP-Me to investigate bacteriorhodopsin-lipid interactions

Jin Cui, Satoshi Kawatake, Yuichi Umegawa, Sébastien Lethu, Masaki Yamagami, Shigeru Matsuoka, Fuminori Sato, Nobuaki Matsumori, Michio Murata

Research output: Contribution to journalArticle

4 Citations (Scopus)

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 2H-labelled analogue was observed in 2H 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.

Original languageEnglish
Pages (from-to)10279-10284
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number41
DOIs
Publication statusPublished - Jan 1 2015

Fingerprint

Bacteriorhodopsins
lipids
esters
Phospholipids
analogs
Lipids
synthesis
interactions
integrity
Purple Membrane
chemistry
pumps
membranes
proteins
Proton Pumps
Organophosphonates
nuclear magnetic resonance
protons
Liposomes
PGP-Me

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Stereoselective synthesis of the head group of archaeal phospholipid PGP-Me to investigate bacteriorhodopsin-lipid interactions. / Cui, Jin; Kawatake, Satoshi; Umegawa, Yuichi; Lethu, Sébastien; Yamagami, Masaki; Matsuoka, Shigeru; Sato, Fuminori; Matsumori, Nobuaki; Murata, Michio.

In: Organic and Biomolecular Chemistry, Vol. 13, No. 41, 01.01.2015, p. 10279-10284.

Research output: Contribution to journalArticle

Cui, Jin ; Kawatake, Satoshi ; Umegawa, Yuichi ; Lethu, Sébastien ; Yamagami, Masaki ; Matsuoka, Shigeru ; Sato, Fuminori ; Matsumori, Nobuaki ; Murata, Michio. / Stereoselective synthesis of the head group of archaeal phospholipid PGP-Me to investigate bacteriorhodopsin-lipid interactions. In: Organic and Biomolecular Chemistry. 2015 ; Vol. 13, No. 41. pp. 10279-10284.
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AU - Sato, Fuminori

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