PMID: 3366545Feb 1, 1988

Thermolysin and alpha-chymotrypsin mediated synthesis of tripeptides containing proline

International Journal of Peptide and Protein Research
E ChengM Tominaga

Abstract

The tripeptides Z-Pro-Leu-Gly-OEt, Z-Pro-Leu-Gly-NH2 and Z-Pro-Leu-Gly-OBzl were synthesized by thermolysin and alpha-chymotrypsin catalysis. The optimum conditions for the couplings between Z-Pro-OH and H-Leu-OEt or H-Leu-Gly-OEt catalysed by thermolysin were determined by a systematic study involving analysis of pH effect, ammonium sulfate concentration, reaction time, enzyme concentration, and relative proportion of the carboxyl and amine components. The best yield obtained for Z-Pro-Leu-OEt was 77% and for Z-Pro-Leu-Gly-OEt, 100%. Z-Pro-Leu-OEt was coupled to H-Gly-OEt, H-Gly-NH2 and H-Gly-OBzl. The best conditions to obtain Z-Pro-Leu-Gly-OEt and Z-Pro-Leu-Gly-NH2 were determined by the study of some factors that affect the reaction yield, such as organic solvent presence, substrate ratio and aqueous and organic solvent ratio. The yield obtained under optimum synthesis conditions was 55% for Z-Pro-Leu-Gly-OEt and 61% for Z-Pro-Leu-Gly-NH2. Z-Pro-Leu-Gly-OBzl was synthesized with 42% yield.

References

Nov 1, 1978·Journal of Biochemistry·T Oka, K Morihara
Jun 1, 1977·The Biochemical Journal·K Morihara, T Oka
May 1, 1967·Tetrahedron·M Goodman, W J McGahren
May 1, 1984·International Journal of Peptide and Protein Research· Mitin YuV Gorbunova EYu
Sep 1, 1980·Journal of Biochemistry·T Oka, K Morihara

Citations

Apr 1, 1991·International Journal of Peptide and Protein Research·M T MirandaM Tominaga
Feb 1, 1991·International Journal of Peptide and Protein Research·M T Miranda, M Tominaga
Aug 13, 2008·Bioorganicheskaia khimiia·A V BeliaevaI Iu Filippova

Related Concepts

Avazyme
Oligopeptides
Proline
Thermolysin

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