Enantioselective inclusion of pyrene-1-sulfonate salts of α-amino acids with crystals of α-cyclodextrin

Ikuko Miyoshi, Yuichi Kitamoto, Tetsuya Maeda, Naoya Morohashi, Tetsutaro Hattori

研究成果: Article査読

3 被引用数 (Scopus)

抄録

Enantioselective inclusion of α-amino acids with crystals of α-cyclodextrin (α-CD) has been achieved by converting the amino acids into sulfonate salts with pyrene-1-sulfonic acid (PyS). For example, crystals of α-CD selectively include L-leucine/PyS (1:1) salt in a host/guest ratio of ∼1 with 92%ee from a solution of the racemic salt in ethanol/N-methylformamide (91:9) at 40 °C. Under conditions optimized for individual amino acids, the PyS salts of valine, phenylalanine, and methionine are also included with good enantioselectivities (up to 86%ee). Mechanistic studies for the inclusion of leucine/PyS salt reveals that the enantioselectivity originates from the difference in stability between the inclusion complexes of D- and L-leucine/PyS salts with α-CD in crystals.

本文言語English
論文番号131100
ジャーナルTetrahedron
76
16
DOI
出版ステータスPublished - 2020 4 17

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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