Chiral bis-chlorin: Enantiomer resolution and absolute configuration determination

被引：21

作者：

Borovkov, VV

Muranaka, A

Hembury, GA

Origane, Y

Ponomarev, GV

Kobayashi, N

Inoue, Y

机构：

[1] JST, ICORP, Entropy Control Project, Toyonaka, Osaka 5600085, Japan

[2] Tohoku Univ, Dept Chem, Grad Sch Sci, Sendai, Miyagi 9808578, Japan

[3] Russian Acad Med Sci, Inst Biomed Chem, Moscow 119832, Russia

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 06期

关键词：

D O I：

10.1021/ol0474913

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A racemic mixture of the ethane-bridged bis(zinc octaethylchlorin) was successfully resolved for the first time to yield two enantiomers that exhibit substantial CD signals in the regions of chlorin B and Q transitions. The absolute configuration of the corresponding enantiomers was assigned and the origin of its high optical activity was rationalized through a combined spectral, crystallographic, and theoretical analysis.

引用

收藏

页码：1015 / 1018

页数：4

相关论文

共 34 条

[21] On the theory of optical rotatory power [J].

Kirkwood, JG .

JOURNAL OF CHEMICAL PHYSICS, 1937, 5 (06) :479-491

[22] ATOMIC MODEL OF PLANT LIGHT-HARVESTING COMPLEX BY ELECTRON CRYSTALLOGRAPHY [J].

KUHLBRANDT, W ;

WANG, DN ;

FUJIYOSHI, Y .

NATURE, 1994, 367 (6464) :614-621

[23] The physical significance of optical rotatory power. [J].

Kuhn, W .

TRANSACTIONS OF THE FARADAY SOCIETY, 1930, 26 :0293-0307

[24] CRYSTAL-STRUCTURE OF AN INTEGRAL MEMBRANE LIGHT-HARVESTING COMPLEX FROM PHOTOSYNTHETIC BACTERIA [J].

MCDERMOTT, G ;

PRINCE, SM ;

FREER, AA ;

HAWTHORNTHWAITELAWLESS, AM ;

PAPIZ, MZ ;

COGDELL, RJ ;

ISAACS, NW .

NATURE, 1995, 374 (6522) :517-521

[25] Multifunctional and chiral porphyrins: Model receptors for chiral recognition [J].

Ogoshi, H ;

Mizutani, T .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (02) :81-89

[26]

Pandey R.K., 2000, The Porphyrin Handbook, V6, P157

[27] Theoretical analysis of the porphyrin-porphyrin exciton interaction in circular dichroism spectra of dimeric tetraarylporphyrins [J].

Pescitelli, G ;

Gabriel, S ;

Wang, YK ;

Fleischhauer, J ;

Woody, RW ;

Berova, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (25) :7613-7628

[28] Chiral sign induction by vortices during the formation of mesophases in stirred solutions [J].

Ribó, JM ;

Crusats, J ;

Sagués, F ;

Claret, J ;

Rubires, R .

SCIENCE, 2001, 292 (5524) :2063-2066

[29] STRUCTURE AND CONFORMATION OF PHOTOSYNTHETIC PIGMENTS AND RELATED-COMPOUNDS .6. THE 1ST CRYSTAL-STRUCTURE OF A COVALENTLY-LINKED CHLORIN DIMER - 20,20'-ETHYLENEBIS(TRANS-2,3,7,8,12,13,17,18-OCTAETHYLCHLORIN) [J].

SENGE, MO ;

HOPE, H ;

SMITH, KM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (01) :11-16

[30] MESO-METHYLPORPHYRINS AND MESO-CHLORINS [J].

SMITH, KM ;

BISSET, GMF ;

BUSHELL, MJ .

BIOORGANIC CHEMISTRY, 1980, 9 (01) :1-26

← 1 2 3 4 →