Chiral recognition of amino acid enantiomers applying association models of amino acid derivatives forming intermolecular hydrogen bonds

✍ Scribed by Akira Dobashi; Shoji Hara

• Book ID: 104217144
• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 150 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)81694-9

✦ Synopsis

Chelate-like association of amino acid derivatives made up by intermolecular NH**O=C hydrogen bonds can function as chiroselective complexation for resolution of D-and L-amino acid derivatives. Recognition of molecular chiralities is made on the basis of the different affinities of chiral molecules toward enantiomers to be resolved'. We report in this paper that the association modes of amino acid derivatives consisting of intermolecular NH**O=C hydrogen bonds2 can function to bring about chiroselective complexation in the resolution of the D and L enantiomers of amino acid derivatives. Chiral N-acetyl-L-valine tert-butylamide was used as a chiral resolving agent in liquid-solid chromatography.

This resolving agent can offer hydrogen bonding sites through two amide units to the amino acid derivatives to be resolved.