PMID: 3792308Dec 15, 1986

Kinetics and equilibrium of enzymatic synthesis of peptides in aqueous/organic biphasic systems. Thermolysin-catalyzed synthesis of N-(benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester

European Journal of Biochemistry
K NakanishiR Matsuno

Abstract

We studied kinetics and the equilibrium relationship for the thermolysin-catalyzed synthesis of N-(benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester (Z-Asp-PheOMe) from N-(benzyloxycarbonyl)-L-aspartic acid (Z-Asp) and L-phenylalanine methyl ester (PheOMe) in an aqueous-organic biphasic system. This is a model reaction giving a condensation product with dissociating groups. The kinetics for the synthesis of Z-Asp-PheOMe in aqueous solution saturated with ethyl acetate was expressed by a rate equation for the rapid-equilibrium random bireactant mechanism, and the reverse hydrolysis reaction was zero-order with respect to Z-Asp-PheOMe concentration. The courses of synthesis of Z-Asp-PheOMe in the biphasic system were well explained, by the rate equations obtained for the aqueous solution and by the partition of substrate and condensation product between the both phases. The rate of synthesis in the biphasic system was much lower than in aqueous solution due to the unfavorable partition of PheOMe in the aqueous phase. The equation for the equilibrium yield of Z-Asp-PheOMe in the biphasic system was derived assuming that only the non-ionized forms of the substrate and condensation product exist in the organic phase. It was...Continue Reading

References

Sep 1, 1977·Biotechnology and Bioengineering·A M KlibanovI V Berezin
Mar 12, 1974·Biochemistry·J FederB S Wildi
May 7, 1969·Journal of the American Chemical Society·R H MazurA H Goldkamp
Jun 1, 1983·Proceedings of the National Academy of Sciences of the United States of America·S I Wayne, J S Fruton
Mar 13, 1981·Biochimica Et Biophysica Acta·K Martinek, A N Semenov

Citations

Jul 19, 2008·Biotechnology and Bioengineering·Y IsonoM Nakajima
Mar 17, 1999·Journal of Molecular Recognition : JMR·L YeK Mosbach
May 1, 1994·Biotechnology and Bioengineering·T NagayasuK Nakanishi
Jul 1, 1994·Biotechnology and Bioengineering·S A WilsonK Peek
Mar 1, 1990·Applied Microbiology and Biotechnology·K NakanishiR Matsuno
Jan 24, 1991·Journal of Immunological Methods·H H Weetall
Oct 12, 2000·Enzyme and Microbial Technology·M B DienderJ J Heijnen
Oct 20, 2005·Journal of Bioscience and Bioengineering·M MiyanagaK Nakanishi
Oct 20, 2005·Journal of Bioscience and Bioengineering·M MiyanagaK Nakanishi
Jan 1, 1990·Annals of the New York Academy of Sciences·K Nakanishi, R Matsuno
Jun 20, 2014·ACS Medicinal Chemistry Letters·Gabriel BirraneManuel A Navia
Apr 15, 2004·Biotechnology and Bioengineering·Iulian M BobeHaruo Ishikawa
Aug 13, 2008·Bioorganicheskaia khimiia·A V BeliaevaI Iu Filippova
May 26, 2010·Applied Microbiology and Biotechnology·Jiro ArimaTadanori Aimi
Nov 1, 1994·International Journal of Peptide and Protein Research·M P BemquererM Tominaga
Nov 30, 1992·Annals of the New York Academy of Sciences·R MatsunoK Nakanishi

Related Concepts

Ethyl acetate
N-benzyloxycarbonyl-aspartylphenylalanine methyl ester, (L-beta-Asp)-isomer
Acetic Acids
Ampholytes
Catalysis
Dipeptides
Hydrogen-Ion Concentration
Hydrolysis
Mathematics
Solvents

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