The role of the membrane-assisted hydrophobic interaction between di-, tri-, or tetrapeptide catalysts and amino acid esters for the enhancement of stereoselective hydrolysis reactions
✍ Scribed by Katsutoshi Ohkubo; Kenji Urabe; Satoshi Usui; Takashi Sagawa
- Publisher
- John Wiley and Sons
- Year
- 1996
- Tongue
- English
- Weight
- 365 KB
- Volume
- 17
- Category
- Article
- ISSN
- 1022-1336
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✦ Synopsis
Abstract
The peptide catalyst having the amino acid sequence (Z‐L‐Leu (or Phe)‐L‐His) was found to be the most stereoselective among the L‐histidyl group‐containing di‐, tri‐, or tetrapeptide catalysts in the hydrolysis of enantiomeric amino acid substrates in vesicular membranes. The role of the membrane‐assisted hydrophobic interaction between the peptide catalyst and enantiomeric substrates for the improvement of the hydrolysis stereoselectivity was demonstrated by means of direct measurements of __n__uclear __O__verhauser __e__ffect __s__pectroscopy (NOESY) spectra of the interaction system and by the extremely high stereoselectivity itself obtained by intensifying the membrane‐promoted hydrophobic interaction between the catalyst and the substrates.