A novel cis-peptide bond motif inducing beta-turn type VI. The synthesis of enkephalin analogues modified with 4-aminopyroglutamic acid

• Autorzy: Kaczmarek K. , Kaleta M. , Chung N.N. , Schiller P.W. , Zabrocki J.
• Języki publikacji: EN

Abstrakty

EN

A new pathway leading to a mixture of four isomers of 4-aminopyroglutamic acid is described. Michael type addition of Z-ΔAla-OMe to enolates prepared from acylaminomalonates, followed by hydrolysis and decarboxylation give protected 4-aminopyroglutamic acid with the cis'trans ratio approximately 3:2. This mixture was incorporated into Leu-enkephalin (position 2-3). After separation of peptides it appeared that all analogues were essentially inactive in guinea pig ileum and mouse vas deferens bioassays.

Słowa kluczowe

EN

4-aminopyroglutamic acid; benzyloxycarbonyl; cis-geometry; peptide bioactivity; cis-amide bond; enkephalin analogue; cis-peptide; trifluoroacetic acid

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 2001
• Tom: 48
• Numer: 4
• Opis fizyczny: p.1159-1163,fig.

Twórcy

autor

Kaczmarek K.

• Technical University of Lodz, 90-924 Lodz, Poland

autor

Kaleta M.

autor

Chung N.N.

autor

Schiller P.W.

autor

Zabrocki J.

Bibliografia

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• 2.Kaczmarek,K., Zabrocki, J., Lachwa, M. & Lipkowski, A. (1999) in Peptides 1998 (Proc. 25th Eur. Peptide Symposium), (Bajusz, S. & Hudecz, F., eds.) pp. 668-669, Akademiai Kiado, Budapest.
• 3.Schiller, P.W., Lipton, A., Horrobin, D.F. & Bodanszky, M. (1978) Biochem. Biophys. Res. Commun. 85, 1332-1338.
• 4.DiMaio, J., Nguyen, T.M.-D., Lemieux, C. & Schiller, P.W. (1982) J. Med. Chem. 25, 1432-1438.