Reduction of vinyl groups in naturally occurring chlorophylls-a

被引：14

作者：

Tamiaki, Hitoshi ^{[1
]}

Takekoshi, Daisuke ^{[1
]}

Mizoguchi, Tadashi ^{[1
]}

机构：

[1] Ritsumeikan Univ, Dept Biosci & Biotechnol, Fac Sci & Engn, Shiga 5258577, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2011年 / 19卷 / 01期

基金：

日本学术振兴会;

关键词：

Biosynthesis; Hydrogenation; Regioisomer; Site-selectivity; Substitution effect; IDENTIFICATION; 17-PROPIONATE; EVOLUTION;

D O I：

10.1016/j.bmc.2010.11.056

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

3,8-Divinyl-chlorophyll(Chl)-a possessing a phytyl ester was hydrogenated in acetone by rhodium catalyst on alumina to afford 3-vinyl-8-ethyl-, 3-ethyl-8-vinyl- and 3,8-diethyl-Chls. The ratio of produced 3-ethyl-8-vinyl- over 3-vinyl-8-ethyl-Chls was determined to be 1.2, indicating that the reactivity of the 3-vinyl group was slightly higher than that of the 8-vinyl group. Catalytic hydrogenation of divinyl-proto-chlorophyll-a possessing a porphyrin pi-skeleton (C17=C18) instead of the above chlorin moiety (C17H-C18H) gave an equal amount of mono-reduced regioisomers. The slight (or no) selectivity is different from that in the enzymatic reduction of divinyl-(proto)chlorophyllides-a lacking a phytyl ester in the bio-synthetic pathway of Chl-a where the sole 8-vinyl group is transformed to the ethyl group. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：52 / 57

页数：6

共 19 条

[1]

BELANGER FC, 1982, J BIOL CHEM, V257, P4849

[2] Making light work of enzyme catalysis: protochlorophyllide oxidoreductase [J].

Heyes, DJ ;

Hunter, CN .

TRENDS IN BIOCHEMICAL SCIENCES, 2005, 30 (11) :642-649

[3]

Kolossov VL, 2010, ADV PHOTOSYNTH RESP, V31, P25

[4] Chlorophyll breakdown and chlorophyll catabolites in leaves and fruit [J].

Kraeutler, Bernhard .

PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2008, 7 (10) :1114-1120

[5] Chlorophyll biosynthesis in bacteria: The origins of structural and functional diversity [J].

Maqueo Chew, Aline Gomez ;

Bryant, Donald A. .

ANNUAL REVIEW OF MICROBIOLOGY, 2007, 61 :113-129

[6] Regulation and evolution of chlorophyll metabolism [J].

Masuda, Tatsuru ;

Fujita, Yuichi .

PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2008, 7 (10) :1131-1149

[7] Structural determination of dihydro- and tetrahydrogeranylgeranyl groups at the 17-propionate of bacterlochlorophylls-α [J].

Mizoguchi, Tadashi ;

Harada, Jiro ;

Tamiaki, Hitoshi .

FEBS LETTERS, 2006, 580 (28-29) :6644-6648

[8] Stereochemical determination of the unique acrylate moiety at the 17-position in chlorophylls-c from a diatom Chaetoseros calcitrans and its effect upon electronic absorption properties [J].

Mizoguchi, Tadashi ;

Nagai, Chihiro ;

Kunieda, Michio ;

Kimura, Yuki ;

Okamura, Atsushi ;

Tamiaki, Hitoshi .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (10) :2120-2126

[9] X-ray crystal structure of the light-independent protochlorophyllide reductase [J].

Muraki, Norifumi ;

Nomata, Jiro ;

Ebata, Kozue ;

Mizoguchi, Tadashi ;

Shiba, Tomoo ;

Tamiaki, Hitoshi ;

Kurisu, Genji ;

Fujita, Yuichi .

NATURE, 2010, 465 (7294) :110-U124

[10] Identification of a vinyl reductase gene for chlorophyll synthesis in Arabidopsis thaliana and implications for the evolution of Prochlorococcus species [J].

Nagata, N ;

Tanaka, R ;

Satoh, S ;

Tanaka, A .

PLANT CELL, 2005, 17 (01) :233-240

← 1 2 →