Chiral recognition of non-natural α-amino acids

Jean François Gal, Michele Stone, Carlito B Lebrilla

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

The gas-phase guest exchange reactions of a number of non-natural α-amino acids complexed to permethylated β-cyclodextrin were examined with Fourier transform mass spectrometry. The enantioselectivity of the reactions were determined. Molecular modeling calculations were performed to support the experimental results. The amino acids included homoserine, cis-4-hydroxyproline, allo-threonine, and allo-isoleucine. Results from molecular modeling calculations suggest that enantioselectivity is governed by differences in the binding interaction between the amino acid host and the permethylated β-cyclodextrin guest.

Original languageEnglish (US)
Pages (from-to)259-267
Number of pages9
JournalInternational Journal of Mass Spectrometry
Volume222
Issue number1-3
DOIs
StatePublished - Jan 1 2003

Fingerprint

amino acids
Amino acids
Molecular modeling
Enantioselectivity
Cyclodextrins
Amino Acids
Hydroxyproline
Homoserine
Isoleucine
Threonine
Mass spectrometry
Fourier transforms
mass spectroscopy
Gases
vapor phases
interactions

Keywords

  • Amino acids
  • Chiral recognition
  • Cyclodextrin
  • Host-guest complexes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Spectroscopy

Cite this

Chiral recognition of non-natural α-amino acids. / Gal, Jean François; Stone, Michele; Lebrilla, Carlito B.

In: International Journal of Mass Spectrometry, Vol. 222, No. 1-3, 01.01.2003, p. 259-267.

Research output: Contribution to journalArticle

Gal, Jean François ; Stone, Michele ; Lebrilla, Carlito B. / Chiral recognition of non-natural α-amino acids. In: International Journal of Mass Spectrometry. 2003 ; Vol. 222, No. 1-3. pp. 259-267.
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