Synthesis of chlorophyll-f analogs possessing the 2-formyl group by modifying chlorophyll-a

Meiyun Xu; Yusuke Kinoshita; Hitoshi Tamiaki

doi:10.1016/j.bmcl.2014.06.022

Synthesis of chlorophyll-f analogs possessing the 2-formyl group by modifying chlorophyll-a

Bioorg Med Chem Lett. 2014 Aug 15;24(16):3997-4000. doi: 10.1016/j.bmcl.2014.06.022. Epub 2014 Jun 18.

Authors

Meiyun Xu¹, Yusuke Kinoshita¹, Hitoshi Tamiaki²

Affiliations

¹ Graduate School of Life Sciences, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan.
² Graduate School of Life Sciences, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan. Electronic address: tamiaki@fc.ritsumei.ac.jp.

PMID: 24998380
DOI: 10.1016/j.bmcl.2014.06.022

Abstract

A methyl group at the 2-position of methyl mesopyropheophorbide-a was transformed to the 2-formyl group to give methyl mesopyropheophorbide-f, one of the chlorophyll-f analogs. The 2-formylation moved the redmost electronic absorption band in a solution to a longer wavelength and the bathochromic shift was comparable to that by the 3-formylation. Zinc complex of the synthetic compound in solutions showed similar visible absorption spectra as those of naturally occurring chlorophyll-f.

Keywords: Electronic absorption spectra; Oxidation; Photosynthesis; Substitution effect.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chlorophyll / analogs & derivatives
Chlorophyll / chemical synthesis*
Chlorophyll / chemistry
Molecular Conformation

Substances

Chlorophyll