Abstract
Carboxypeptidase Y catalyzes in a biphasic system containing carbon tetrachloride and carbonate buffer the reaction ofZ-Phe-OMe and variousZ-andBoc-protected dipeptide methyl esters with Val-NH2 and Leu-NH2, respectively. This method has been applied to the synthesis of the corresponding N-protected tripeptide amides on a preparative scale. Using a substrate—nucleophile ratio of only 1:2 or 1:3 the peptide derivatives are obtained in yields of 56–97%.
Zusammenfassung
Carboxypeptidase Y katalysiert in einem Zweiphasensystem aus Tetrachlormethan und Carbonatpuffer die Reaktion vonZ-Phe-OMe und verschiedenenZ- undBoc-geschützten Dipeptidmethylestern mit Val-NH2 bzw. Leu-NH2. Nach diesem Verfahren werden die entsprechenden N-geschützen Tripeptidamide in präparativem Maßstab hergestellt. Bei einem Substrat-Nucleophil-Verhältnis von nur 1:2 oder 1:3 erhält man die Peptidderivate in Ausbeuten von 56–97%.
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Abbreviations: IUPAC-IUB rules for peptides are followed, see Eur. J. Biochem.27, 201 (1972).Boc=tert-butyloxycarbonyl,Z=benzyloxycarbonyl,-OMe=methyl ester, HPLC=high performance liquid chromatography, TLC=thin layer chromatography,CPD-Y=carboxypeptidase Y.
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Kuhl, P., Zapevalova, N.P., Könnecke, A. et al. Model studies on carboxypeptidase Y catalyzed peptide synthesis in an aqueous-organic two-phase system. Monatsh Chem 114, 343–347 (1983). https://doi.org/10.1007/BF00798957
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DOI: https://doi.org/10.1007/BF00798957