Stereochemical assignment of the unique electron acceptor 5'-hydroxyphylloquinone, a polar analog of vitamin K1 in photosystem I

Makiko Kosugi; Changwoo Lee; Tomonori Misaki; Yasuhiro Kashino; Morifumi Fujita; Takashi Sugimura

doi:10.1080/09168451.2017.1385381

Stereochemical assignment of the unique electron acceptor 5'-hydroxyphylloquinone, a polar analog of vitamin K₁ in photosystem I

Biosci Biotechnol Biochem. 2017 Dec;81(12):2244-2252. doi: 10.1080/09168451.2017.1385381. Epub 2017 Nov 3.

Authors

Makiko Kosugi^{1

2}, Changwoo Lee³, Tomonori Misaki³, Yasuhiro Kashino¹, Morifumi Fujita³, Takashi Sugimura³

Affiliations

¹ a Department of Life Science, Graduate School of Life Science , University of Hyogo , Kamigori , Japan.
² b Department of Biological Sciences, Faculty of Science and Engineering , Chuo University , Tokyo , Japan.
³ c Department of Material Science, Graduate School of Material Science , University of Hyogo , Kamigori , Japan.

PMID: 29098938
DOI: 10.1080/09168451.2017.1385381

Abstract

A unique electron-accepting analog of vitamin K₁ found in photosystem I in several species of oxygenic photosynthetic microorganisms was confirmed to be 5'-hydroxyphylloquinone (1) through stereo-uncontrolled synthesis. Furthermore, the stereochemistry of 1 obtained from Synechococcus sp. PCC 7942 was assigned to be 5'S using proline-catalyzed stereocontrolled reactions.

Keywords: 5′-hydroxyphylloquinone; electron acceptor; photosystem I.

MeSH terms

Electron Transport
Photosystem I Protein Complex / metabolism*
Stereoisomerism
Synechococcus / metabolism
Vitamin K 1 / analogs & derivatives*
Vitamin K 1 / chemistry
Vitamin K 1 / metabolism

Substances

5'-monohydroxyphylloquinone
Photosystem I Protein Complex
Vitamin K 1