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

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

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.

Original languageEnglish
Article number131100
JournalTetrahedron
Volume76
Issue number16
DOIs
Publication statusPublished - 2020 Apr 17

Keywords

  • Amino acid
  • Cyclodextrin
  • Enantioselective inclusion
  • Nanoporous molecular crystal

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Enantioselective inclusion of pyrene-1-sulfonate salts of α-amino acids with crystals of α-cyclodextrin'. Together they form a unique fingerprint.

Cite this