Chiral recognition and chiral sensing using zinc porphyrin dimers

Takashi Hayashi, Toshihiro Aya, Masanori Nonoguchi, Tadashi Mizutani, Yoshio Hisaeda, Susumu Kitagawa, Hisanobu Ogoshi

Research output: Contribution to journalArticle

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Abstract

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.

Original languageEnglish
Pages (from-to)2803-2811
Number of pages9
JournalTetrahedron
Volume58
Issue number14
DOIs
Publication statusPublished - Apr 1 2002

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Dimers
Diamines
Lysine
Derivatives
Cystine
Enantiomers
Chirality
Enantioselectivity
Complexation
Amides
Zinc
Nitrogen
zinc hematoporphyrin
Amino Acids

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Hayashi, T., Aya, T., Nonoguchi, M., Mizutani, T., Hisaeda, Y., Kitagawa, S., & Ogoshi, H. (2002). Chiral recognition and chiral sensing using zinc porphyrin dimers. Tetrahedron, 58(14), 2803-2811. https://doi.org/10.1016/S0040-4020(02)00166-7

Chiral recognition and chiral sensing using zinc porphyrin dimers. / Hayashi, Takashi; Aya, Toshihiro; Nonoguchi, Masanori; Mizutani, Tadashi; Hisaeda, Yoshio; Kitagawa, Susumu; Ogoshi, Hisanobu.

In: Tetrahedron, Vol. 58, No. 14, 01.04.2002, p. 2803-2811.

Research output: Contribution to journalArticle

Hayashi, T, Aya, T, Nonoguchi, M, Mizutani, T, Hisaeda, Y, Kitagawa, S & Ogoshi, H 2002, 'Chiral recognition and chiral sensing using zinc porphyrin dimers', Tetrahedron, vol. 58, no. 14, pp. 2803-2811. https://doi.org/10.1016/S0040-4020(02)00166-7
Hayashi T, Aya T, Nonoguchi M, Mizutani T, Hisaeda Y, Kitagawa S et al. Chiral recognition and chiral sensing using zinc porphyrin dimers. Tetrahedron. 2002 Apr 1;58(14):2803-2811. https://doi.org/10.1016/S0040-4020(02)00166-7
Hayashi, Takashi ; Aya, Toshihiro ; Nonoguchi, Masanori ; Mizutani, Tadashi ; Hisaeda, Yoshio ; Kitagawa, Susumu ; Ogoshi, Hisanobu. / Chiral recognition and chiral sensing using zinc porphyrin dimers. In: Tetrahedron. 2002 ; Vol. 58, No. 14. pp. 2803-2811.
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