Chiral recognition and chiral sensing using zinc porphyrin dimers

被引：67

作者：

Hayashi, T ^{[1
]}

Aya, T

Nonoguchi, M

Mizutani, T

Hisaeda, Y

Kitagawi, S

Ogoshi, H

机构：

[1] Kyushu Univ, Grad Sch Engn, Dept Chem & Biochem, Fukuoka 8128581, Japan

[2] Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, Kyoto 6068501, Japan

[3] Fukui Natl Coll Technol, Sabae 9168507, Japan

来源：

TETRAHEDRON | 2002年 / 58卷 / 14期

关键词：

zinc porphyrin porphyrin dimer; chiral recognition; chiral sensing;

D O I：

10.1016/S0040-4020(02)00166-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral zinc porphyrin dimer linked by the (S)-NMe2 or (R)-2,2'-dimethoxy-1,1'-binaphthyl tightly binds diamines via a zinc-nitrogen coordinated ditopic interaction. In particular, the zinc porphyrin displays excellent enantioselectivity towards Lys. The D/L selectivity is determined to be 11-12 for the lysine derivatives. The achiral zinc porphyrin dimers linked by biphenyl unit exhibit a significantly induced CD in the Soret region in the presence of chiral diamines such as lysine amides and cystine diesters, indicating that the chirality of the amino acid derivatives can be monitored upon the complexation with the achiral zinc porphyrin dimer. These results conclude that the zinc porphyrin dimers linked by rigid spacers may be good receptors to discriminate two enantiomers or monitor the absolute configuration of a diamine. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：2803 / 2811

页数：9

共 54 条

[1] Resolution of a porphyrin analogue of Troger's base by making use of ligand binding affinity differences of the enantiomers [J].

Allen, PR ;

Reek, JNH ;

Try, AC ;

Crossley, MJ .

TETRAHEDRON-ASYMMETRY, 1997, 8 (08) :1161-1164

[2] MOLECULAR RECOGNITION .4. MOLECULAR RECOGNITION IN THE TERNARY-SYSTEMS OF A TRIFUNCTIONAL CHIRAL METALLOPORPHYRIN, AMINO ESTERS, AND HPLC ADSORBENT [J].

AOYAMA, Y ;

UZAWA, T ;

SAITA, K ;

TANAKA, Y ;

TOI, H ;

OGOSHI, H .

TETRAHEDRON LETTERS, 1988, 29 (41) :5271-5274

[3] PREPARATION AND OPTICAL RESOLUTION OF NOVEL 5,10-DIARYLOCTAETHYLPORPHYRINS WITH C-2 SYMMETRY [J].

AOYAMA, Y ;

SAITA, K ;

TOI, H ;

OGOSHI, H .

TETRAHEDRON LETTERS, 1987, 28 (41) :4853-4856

[4] UNEXPECTED TETRACOORDINATED IRON(II) BIS-STRAPPED CHIRAL PORPHYRIN BEARING A NITROGEN BASE ON ONE HANDLE [J].

BOITREL, B ;

LECAS, A ;

ROSE, E .

TETRAHEDRON LETTERS, 1988, 29 (44) :5653-5656

[5] Recognition by a solubilized receptor: Hydrogen bonding, solvophobic interactions, and solvent engineering inside micelles [J].

BonarLaw, RP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (50) :12397-12407

[6] Elucidation of the mechanism of supramolecular chirality inversion in bis(zinc porphyrin) by dynamic approach using CD and 1H NMR spectroscopy [J].

Borovkov, VV ;

Lintuluoto, JM ;

Inone, Y .

JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (40) :9213-9219

[7] Supramolecular chirogenesis in bis(zinc porphyrin): An absolute configuration probe highly sensitive to guest structure [J].

Borovkov, VV ;

Lintuluoto, JM ;

Inoue, Y .

ORGANIC LETTERS, 2000, 2 (11) :1565-1568

[8] Temperature effect on supramolecular chirality induction in bis(zinc porphyrin) [J].

Borovkov, VV ;

Lintuluoto, JM ;

Fujiki, M ;

Inoue, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (18) :4403-4407

[9] Supramolecular chirogenesis in zinc porphyrins: Mechanism, role of guest structure, and application for the absolute configuration determination [J].

Borovkov, VV ;

Lintuluoto, JM ;

Inoue, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (13) :2979-2989

[10] ASYMMETRIC OXIDATION OF SULFIDES CATALYZED BY AN IRON COMPLEX OF C2-CHIRAL STRAPPED PORPHYRIN AS A CONCEPTUALLY NEW P-450 MODEL CATALYST [J].

CHIANG, LC ;

KONISHI, K ;

AIDA, T ;

INOUE, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (03) :254-256

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