Supramolecular chirality induction in bis(zinc porphyrin) by amino acid derivatives: Rationalization and applications of the ligand bulkiness effect

Chirality

Volumn 13, Issue 6, 2001, Pages 329-335

  Borovkov, Victor V ^a   Yamamoto, Naoyuki ^b   Lintuluoto, Juha M ^a   Tanaka, Takumi ^b   Inoue, Yoshihisa ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b FUJIFILM Wako Pure Chemical Corporation   (Japan)

Author keywords

Absolute configuration; Amino acid; Bulkiness effect; Circular dichroism; Conformation; Induced chirality; Ligand; Porphyrin; Supramolecular chemistry

Indexed keywords

AMINO ACID; BIZ(ZINC PORPHYRIN); CARBON; ETHANE; LIGAND; PORPHYRIN; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; CONFORMATION; LIGAND BINDING; PRIORITY JOURNAL; STEREOSPECIFICITY;

EID: 0034984125     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.1039     Document Type: Article

References (8)

1. Tsukube H, Shinoda S. Lanthanide complexes as smart CD probes for chirality sensing of biological substrates. Enantiomer 2000;5:13-22.
2. Tsukube H, Wada M, Shinoda S, Tamiaki H. Porphyrinatoerbium-crown ether conjugate for synergistic binding and chirality sensing of zwitterionic amino acids. Chem Commun 1999:1007-1008.
3. Tsukube H, Hosokubo M, Wada M, Shinoda S, Tamiaki H. Chirality probing of amino alcohols with lanthanide complexes via induced circular dichroism spectroscopy. J Chem Soc Dalton Trans 1999:11-12.
4. Mizuno Y, Aida T, Yamaguchi K. Chirality-memory molecule: crystallographic and spectroscopic studies on dynamic molecular recognition events by fully substituted chiral porphyrins. J Am Chem Soc 2000; 122:5278-5285.
5. Huang X, Borhan B, Rickman BH, Nakanishi K, Berova N. Zinc porphyrin tweezer in host-guest complexation: determination of absolute configuration of primary monoamines by circular dichroism. Chem Eur J 2000;6:216-224.
6. Huang X, Rickman BH, Borhan B, Berova N, Nakanishi K. Zinc porphyrin tweezer in host-guest complexation: determination of absolute configurations of diamines, amino acids, and amino alcohols by circular dichroism. J Am Chem Soc 1998;120:6185-6186.
7. Borovkov VV, Lintuluoto JM, Fujiki M, Inoue Y. Temperature effect on supramolecular chirality induction in bis(zinc porphyrin). J Am Chem Soc 2000;122:4403-4407.
8. Borovkov W, Lintuluoto JM, Inoue Y. Supramolecular chirogenesis in bis(zinc porphyrin): an absolute configuration probe highly sensitive to guest structure. Org Lett 2000;2:1565-1568.