Structural determination of dihydro- and tetrahydrogeranylgeranyl groups at the 17-propionate of bacterlochlorophylls-α

被引：39

作者：

Mizoguchi, Tadashi ^{[1
]}

Harada, Jiro ^{[1
]}

Tamiaki, Hitoshi ^{[1
]}

机构：

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

来源：

FEBS LETTERS | 2006年 / 580卷 / 28-29期

基金：

日本学术振兴会;

关键词：

bacteriochlorophyll-alpha; dihydrogeranylgeranyl; tetrahydrogeranylgeranyl; chlorophyll biosynthesis; photosynthetic bacteria; NMR; BACTERIOCHLOROPHYLL-A; RHODOPSEUDOMONAS-PALUSTRIS; FUNCTIONAL ASSIGNMENT; INFRARED REGION; CHLOROPHYLL; GENE; CHROMATOGRAPHY; BIOSYNTHESIS; COMPLEXES; CLONING;

D O I：

10.1016/j.febslet.2006.11.020

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：

In the final stage of bacteriochlorophyll (BChl) biosynthesis, the presence of BChl-a molecules possessing dihydrogeranylgeranyl and tetrahydrogeranylgeranyl groups at the 17-propionate has been reported. However, the molecular structures of such BChls-a have not yet been determined in terms of the positions of C=C double bonds in the 17(2)-ester. In this study, we isolated significant amounts of such pure BChis-a from Rhodopseudomonas palustris and determined their structures by both mass spectrometry and H-1 and C-13 NMR spectroscopy. The determined structures enable us to discuss a stepwise reduction from a geranylgeranyl to phytyl substituent. (c) 2006 Federation of European Biochemical Societies.

引用

页码：6644 / 6648

页数：5

共 19 条

[1] Physical mapping and functional assignment of the geranylgeranyl-bacteriochlorophyll reductase gene, bchP, of Rhodobacter sphaeroides [J].

Addlesee, HA ;

Hunter, CN .

JOURNAL OF BACTERIOLOGY, 1999, 181 (23) :7248-7255

[2] Cloning, sequencing and functional assignment of the chlorophyll biosynthesis gene, chlP, of Synechocystis sp PCC 6803 [J].

Addlesee, HA ;

Gibson, LCD ;

Jensen, PE ;

Hunter, CN .

FEBS LETTERS, 1996, 389 (02) :126-130

[3] ISOLATION AND CHARACTERIZATION OF THE DIFFERENT B800-850 LIGHT-HARVESTING COMPLEXES FROM LOW-LIGHT AND HIGH-LIGHT GROWN CELLS OF RHODOPSEUDOMONAS-PALUSTRIS, STRAIN 2.1.6 [J].

EVANS, MB ;

HAWTHORNTHWAITE, AM ;

COGDELL, RJ .

BIOCHIMICA ET BIOPHYSICA ACTA, 1990, 1016 (01) :71-76

[4] Density functional theory calculations of the structure and the 15N and 13C chemical shifts of methyl bacteriopheophorbide a and bacteriochlorophyll a [J].

Facelli, JC .

JOURNAL OF PHYSICAL CHEMISTRY B, 1998, 102 (11) :2111-2116

[5] ABSORPTION AND FLUORESCENCE-SPECTRA OF LIGHT-HARVESTING BACTERIOCHLOROPHYLL-PROTEIN COMPLEXES FROM RHODOPSEUDOMANAS-PALUSTRIS IN THE NEAR-INFRARED REGION [J].

HAYASHI, H ;

MIYAO, M ;

MORITA, S .

JOURNAL OF BIOCHEMISTRY, 1982, 91 (03) :1017-1027

[6] Diastereoselective self-aggregation of synthetic 3-(1-hydroxyethyl)-bacteriopyrochlorophyll-a as a novel photosynthetic antenna model absorbing near the infrared region [J].

Kunieda, M ;

Mizoguchi, T ;

Tamiaki, H .

PHOTOCHEMISTRY AND PHOTOBIOLOGY, 2004, 79 (01) :55-61

[7] Shortcut of the photosynthetic electron transfer in a mutant lacking the reaction center-bound cytochrome subunit by gene disruption in a purple bacterium, Rubrivivax gelatinosus [J].

Nagashima, KVP ;

Shimada, K ;

Matsuura, K .

FEBS LETTERS, 1996, 385 (03) :209-213

[8]

OMATA T, 1983, PLANT CELL PHYSIOL, V24, P1093

[9]

Rudiger W., 2000, The Porphyrin Handbook, V13, P71

[10] Synthesis and optical properties of bacteriochlorophyll-a derivatives having various C3 substituents on the bacteriochlorin π-system [J].

Sasaki, S ;

Tamiaki, H .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (07) :2648-2654

← 1 2 →