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

• Authors: Krzysztof Kaczmarek , Maciej Kaleta , Nga N Chung , Peter W Schiller , Janusz Zabrocki
• Languages of publication: EN

Abstracts

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 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.

Keywords

EN

constrained enkephalin analogues; 4-aminopyroglutamic acid; cis-peptide bond; β-turn mimetic

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2001
• Volume: 48
• Issue: 4
• Pages: 1159-1163

Dates

published

2001

received

2001-10-9

accepted

2001-11-12

Contributors

author

Krzysztof Kaczmarek

• Institute of Organic Chemistry, Technical University of Łódź, 90-924 Łódź, Poland

author

Maciej Kaleta

• Institute of Organic Chemistry, Technical University of Łódź, 90-924 Łódź, Poland

author

Nga N Chung

• Laboratory of Chemical Biology, Clinical Research Institute of Montreal, Montreal, Quebec, Canada

author

Peter W Schiller

• Laboratory of Chemical Biology, Clinical Research Institute of Montreal, Montreal, Quebec, Canada

author

Janusz Zabrocki

• Institute of Organic Chemistry, Technical University of Łódź, 90-924 Łódź, Poland

References

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• 4. DiMaio, J., Nguyen, T.M.-D., Lemieux, C. & Schiller, P.W. (1982) J. Med. Chem. 25, 1432-1438.