Beta-turns induced in bradykinin by (S)-alpha-methylproline.
- Welsh JH Institute of Organic Chemistry, University of Zürich, Switzerland.
- Zerbe O
- von Philipsborn W
- Robinson JA
- 1992-02-10
Published in:
- FEBS letters. - 1992
Amino Acid Sequence
Bradykinin
Magnetic Resonance Spectroscopy
Molecular Conformation
Molecular Sequence Data
Proline
Temperature
English
The ability of (S)-alpha-methylproline (alpha-MePro) to stabilise reverse-turn conformations in the peptide hormone bradykinin (BK = Arg1-Pro2-Pro3-Gly4-Phe5-Ser6-Pro7-Phe8-Arg9) has been investigated. Two BK analogues containing alpha-MePro at position 3 or position 7 were synthesised and their conformations in aqueous solution investigated by NMR spectroscopy. Whereas BK is largely disordered on the NMR time scale both analogues showed ROE connectivities in 2D-ROESY spectra indicative of reverse-turn conformations at both Pro2-Phe5 and Ser6-Arg9, whose formation appears to be cooperative. Some potential applications of alpha-MePro as a reverse-turn mimetic in the construction of synthetic peptide libraries is discussed.
- Language
-
- English
- Open access status
- bronze
- Identifiers
-
- DOI 10.1016/0014-5793(92)80541-n
- PMID 1544400
- Persistent URL
- https://sonar.rero.ch/global/documents/55259
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