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2001 | 48 | 4 | 1159-1163
Article title

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

Content
Title variants
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.
Year
Volume
48
Issue
4
Pages
1159-1163
Physical description
Dates
published
2001
received
2001-10-9
accepted
2001-11-12
References
  • 1. Paul, P.K.C., Burney, P.A., Campbell, M.M. & Osguthorpe, D.J. (1992) Bioorg. Med. Chem. Lett. 2, 141-144.
  • 2. Kaczmarek, K., Zabrocki, J., Łachwa, 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.
Document Type
Publication order reference
YADDA identifier
bwmeta1.element.bwnjournal-article-abpv48i4p1159kz
Identifiers
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