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A novel cis-peptide bond motif inducing β-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.

2001

vol. 48

issue 4

1159-1163

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 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.

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1 Acta Biochimica Polonica

1 2001

1 Chung N. N.

1 Kaczmarek K.

1 Kaleta M.

1 Schiller P. W.

1 Zabrocki J.

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