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

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Kaczmarek K., Kaleta M., Chung N. N., Schiller P. W., Zabrocki J.

Acta Biochimica Polonica

2001

tom 48

nr 4

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.

Ograniczanie wyników

1 Acta Biochimica Polonica

1 Chung N. N.

1 Kaczmarek K.

1 Kaleta M.

1 Schiller P. W.

1 Zabrocki J.

1 2001

Wyniki wyszukiwania

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