Literature DB >> 17497927

A facile synthetic method for conversion of chlorophyll-a to bacteriochlorophyll-c.

Shin-Ichi Sasaki1, Tadashi Mizoguchi, Hitoshi Tamiaki.   

Abstract

A simple synthetic route for converting chlorophyll(Chl)-a to bacteriochlorophyll(BChl)-c is described. Methyl bacteriopheophorbide(MBPhe)-d, easily obtained from Chl-a, was selectively brominated at the 20-position with pyridinium tribromide, and the following Suzuki-coupling with methylboronic acid afforded ca. a 4:1 mixture of desired MBPhe-c (20-Me) and debrominated MBPhe-d (20-H) in quantitative yield. Separation of MBPhe-c, transesterification of the 17-propionate group (Me --> farnesyl), and magnesium insertion successfully led to naturally occurring BChl-c.

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Year:  2007        PMID： 17497927     DOI： 10.1021/jo0703855

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

1.  In vitro synthesis and characterization of bacteriochlorophyll-f and its absence in bacteriochlorophyll-e producing organisms.

Authors:  Hitoshi Tamiaki; Jun Komada; Michio Kunieda; Kazuhiro Fukai; Taichi Yoshitomi; Jiro Harada; Tadashi Mizoguchi
Journal:  Photosynth Res       Date:  2010-12-15       Impact factor: 3.573

Review 2.  De novo synthesis of gem-dialkyl chlorophyll analogues for probing and emulating our green world.

Authors:  Jonathan S Lindsey
Journal:  Chem Rev       Date:  2015-06-12       Impact factor: 60.622

3.  Remarkable regioselective position-10 bromination of bacteriopyropheophorbide-a and ring-B reduced pyropheophorbide-a.

Authors:  Manivannan Ethirajan; Penny Joshi; White H William; Kei Ohkubo; Shunichi Fukuzumi; Ravindra K Pandey
Journal:  Org Lett       Date:  2011-03-21       Impact factor: 6.005

4.  Self-aggregation of synthetic zinc methyl 20-substituted 3-hydroxymethyl-pyropheophorbides as models of bacteriochlorophyll-c.

Authors:  Ayaka Wada; Hitoshi Tamiaki
Journal:  Photosynth Res       Date:  2017-06-22       Impact factor: 3.573
  4 in total

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