Synthesis and self-assembly of amphiphilic zinc chlorins possessing a 31-hydroxy group

被引：39
作者：
Miyatake, T
Tamiaki, H [1 ]
Shinoda, H
Fujiwara, M
Matsushita, T
机构：
[1] Ritsumeikan Univ, Fac Sci & Engn, Dept Biosci & Biotechnol, Otsu, Shiga 5258577, Japan
[2] Ryukoku Univ, Fac Sci & Technol, Dept Chem Mat, Otsu, Shiga 5202194, Japan
来源：
TETRAHEDRON | 2002年 / 58卷 / 50期
关键词：
amphiphilic molecule; chlorophyll; photosynthesis; self-aggregate;
D O I：
10.1016/S0040-4020(02)01328-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Amphiphilic zinc chlorins possessing a 3(1)-hydroxy group were prepared. Non-ionic (oligo)oxyethylene group, anionic sulfonate and cationic quaternary ammonium groups were introduced on the 17-position of a zinc chlorin moiety. All the three kinds of amphiphilic chlorophyll derivatives self-assembled in an aqueous medium to favor a formation of the anti-parallel dimeric structure. In contrast, the amphiphilic zinc chlorins formed large aggregates in non-polar organic solvent. These studies showed self-assemblies of amphiphilic zinc chlorin chromophores were controlled in environments. (C) 2002 Elsevier Science Ltd. All rights reserved.
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收藏
页码：9989 / 10000
页数：12
相关论文
共 43 条
[1]   CIRCULAR-DICHROISM STUDY ON THE DIASTEREOSELECTIVE SELF-ASSEMBLY OF BACTERIOCHLOROPHYLL C(S) [J].
BALABAN, TS ;
HOLZWARTH, AR ;
SCHAFFNER, K .
JOURNAL OF MOLECULAR STRUCTURE, 1995, 349 :183-186
[2]   Autocatalyzed self-aggregation of (31R)-[Et,Et]Bacteriochlorophyll cF molecules in nonpolar solvents.: Analysis of the kinetics [J].
Balaban, TS ;
Leitich, J ;
Holzwarth, AR ;
Schaffner, K .
JOURNAL OF PHYSICAL CHEMISTRY B, 2000, 104 (06) :1362-1372
[3]   Photophysical studies of the pheophorbide a dimer [J].
Eichwurzel, I ;
Stiel, H ;
Röder, B .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 2000, 54 (2-3) :194-200
[4]   Synthesis of a new cationic pyropheophorbide derivative and studies of its aggregation process in aqueous solution [J].
Fabiano, AS ;
Allouche, D ;
Sanejouand, YH ;
Paillous, N .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1997, 66 (03) :336-345
[5]  
FAGES F, 1990, J CHEM SOC P1, P2761
[6]  
Fuhrhop J-H, 1996, COMPREHENSIVE SUPRAM, V9, P407
[7]   PIGMENT ORGANIZATION AND ENERGY-TRANSFER IN GREEN BACTERIA .2. CIRCULAR AND LINEAR DICHROISM SPECTRA OF PROTEIN-CONTAINING AND PROTEIN-FREE CHLOROSOMES ISOLATED FROM CHLOROFLEXUS-AURANTIACUS STRAIN OK-70-FL [J].
GRIEBENOW, K ;
HOLZWARTH, AR ;
VANMOURIK, F ;
VANGRONDELLE, R .
BIOCHIMICA ET BIOPHYSICA ACTA, 1991, 1058 (02) :194-202
[8]   RESONANCE RAMAN-SPECTROSCOPIC STUDY OF METALLOCHLORIN AGGREGATES - IMPLICATIONS FOR THE SUPRAMOLECULAR STRUCTURE IN CHLOROSOMAL BCHL-C ANTENNAE OF GREEN BACTERIA [J].
HILDEBRANDT, P ;
TAMIAKI, H ;
HOLZWARTH, AR ;
SCHAFFNER, K .
JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (08) :2192-2197
[9]   ON THE STRUCTURE OF BACTERIOCHLOROPHYLL MOLECULAR AGGREGATES IN THE CHLOROSOMES OF GREEN BACTERIA - A MOLECULAR MODELING STUDY [J].
HOLZWARTH, AR ;
SCHAFFNER, K .
PHOTOSYNTHESIS RESEARCH, 1994, 41 (01) :225-233
[10]  
Ishil T, 2000, PHOTOCHEM PHOTOBIOL, V71, P567, DOI 10.1562/0031-8655(2000)071<0567:TEOEAT>2.0.CO
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