Synthesis of morphiceptin (Tyr-Pro-Phe-Pro-NH(2)) by dipeptidyl aminopeptidase IV derived from Aspergillus oryzae.
Morphiceptin (Tyr-Pro-Phe-Pro-NH(2)), tetrapeptide, was synthesized using dipeptidyl aminopeptidase IV (DP IV, EC 3.4.14.5) derived from Aspergillus oryzae RIB 915 as a catalyst. Tyr-Pro-OEt was incubated with Phe-Pro-NH(2) in the presence of DP IV under various conditions of temperature, concentrations of ethylene glycol, pH, reaction time, and others. Morphiceptin was obtained at 40% yield under the optimal reaction conditions: substrate, 4 mM Tyr-Pro-OEt.HCl and 20 mM Phe-Pro-NH(2).HCl; enzyme, DP IV, 0.275 nkat; solvent, 60% ethylene glycol containing 20 mM phosphate buffer at pH 7.0; amine, 4.2 mM diisopropylamine at 4 degrees C for 24 h. Amino group protection was unnecessary for synthesis of morphiceptin by DP IV.
Ota
Toru
T
Department of Human Life and Development, Nayoro City College, Nayoro, Hokkaido 096-8641, Japan. ntoruota@nayoro.ac.jp
Itoh
Aki
A
Tachi
Hiroshi
H
Kudoh
Keita
K
Watanabe
Tatsuo
T
Yamamoto
Yuji
Y
Tadokoro
Tadahiro
T
Maekawa
Akio
A
D001236:Aspergillus oryzae / Q000201:enzymology*; D004152:Dipeptidyl-Peptidases and Tripeptidyl-Peptidases / Q000378:metabolism*; D004723:Endorphins / Q000096:biosynthesis*; D019855:Ethylene Glycol; D006863:Hydrogen-Ion Concentration
D004723:Endorphins; C028889:morphiceptin; D004152:Dipeptidyl-Peptidases and Tripeptidyl-Peptidases; D019855:Ethylene Glycol