PMID: 2019475Feb 1, 1991

Thermolysin as a catalyst in enzymatic synthesis of asparagine-containing peptides II

International Journal of Peptide and Protein Research
M T Miranda, M Tominaga

Abstract

Thermolysin was used as a catalyst to obtain the following protected di- and tripeptide esters: Z-Asn-Leu-OEt, Z-Asn-Phe-OEt, Moz-Asn-Leu-Gly-OEt, Boc-Asn-Leu-Gly-OEt, Z-Asn-Leu-Gly-OEt, Moz-Asn-Leu-Gly-OBzl, Moz-Asn-Leu-Gly-OtBu, Moz-Gln-Leu-Gly-OEt, Moz-Asn-Ile-Gly-OEt, and Moz-Asn-Leu-Ala-OEt. These compounds were obtained in pure form and the yields exceeded 50%, except for Moz-Asn-Leu-Gly-OtBu and Boc-Asn-Leu-Gly-OEt. H-Cys(Bzl)-OtBu and H-Cys(Bzl)-Pro-Leu-Gly-NH2 were both inadequate as amino components for obtaining Moz-Asn-Cys(Bzl)-OtBu, Z-Asn-Cys(Bzl)-OtBu and Moz-Asn-Cys(Bzl)-Pro-Leu-Gly-NH2 in the thermolysin-catalyzed reactions. In the attempted synthesis of the protected pentapeptide amide, this protease cleaved the Pro-Leu bond of the amino component H-Cys(Bzl)-Pro-Leu-Gly-NH2 and catalyzed the coupling between the resulting dipeptide amide and Moz-Asn-OH, thus yielding Moz-Asn-Leu-Gly-NH2 as the main product.

References

Feb 1, 1988·International Journal of Peptide and Protein Research·E ChengM Tominaga
Aug 1, 1970·European Journal of Biochemistry·K Morihara, H Tsuzuki
May 1, 1967·Tetrahedron·M Goodman, W J McGahren
Jan 1, 1983·Transactions of the New York Academy of Sciences·J S Fruton
Sep 1, 1980·Journal of Biochemistry·T Oka, K Morihara

Citations

Apr 9, 1999·The Journal of Peptide Research : Official Journal of the American Peptide Society·S RivalJ Wallach
May 1, 1991·International Journal of Peptide and Protein Research·M T MirandaM Tominaga

Related Concepts

Asparagine
Catalysis
Oligopeptides
Thermolysin

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