Trypsin-catalyzed synthesis of dipeptide containing alpha-aminoisobutyric acid using p- and m-(amidinomethyl)phenyl esters as acyl donor.
Two series of inverse substrates, p- and m-(amidinomethyl)phenyl esters derived from N-(tert-butyloxycarbonyl)amino acid, were prepared as acyl donor components for enzymatic peptide synthesis. They were found to be readily coupled with an acyl acceptor such as L-alanine p-nitroanilide to produce dipeptide. An alpha-aminoisobutyric acid containing dipeptide was especially obtained in satisfactory yield. Streptomyces griseus trypsin was a more efficient catalyst than the bovine trypsin. The optimum condition for the coupling reaction was studied by changing the organic solvent, pH, and acyl acceptor concentration. It was found that the enzymatic hydrolysis of the resulting product was negligible.
Sekizaki
Haruo
H
Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido, Japan. sekizaki@hoku-iryo-u.ac.jp
Itoh
Kunihiko
K
Shibuya
Akiyoshi
A
Toyota
Eiko
E
Kojoma
Mareshige
M
Tanizawa
Kazutaka
K
D000215:Acylation; D000578:Amidines / Q000737:chemistry*; D000621:Aminoisobutyric Acids / Q000737:chemistry*; D000818:Animals; D002384:Catalysis; D002417:Cattle; D004151:Dipeptides / Q000138:chemical synthesis*; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared; D013305:Streptomyces griseus / Q000201:enzymology; D013329:Structure-Activity Relationship; D014357:Trypsin / Q000737:chemistry*
D000578:Amidines; D000621:Aminoisobutyric Acids; D004151:Dipeptides; D007202:Indicators and Reagents; C100049:2-aminoisobutyric acid; D014357:Trypsin