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 journalArticlepeer-review

    63 Citations (Scopus)

    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

    All Science Journal Classification (ASJC) codes

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

    Fingerprint

    Dive into the research topics of 'Chiral recognition and chiral sensing using zinc porphyrin dimers'. Together they form a unique fingerprint.

    Cite this