Syntheses of Analogues of the Insect Neuropeptide Proctolin Containing an Oxazole Ring as an Amide Bond Replacement

Three oxazole analogues of the insect neuropeptide proctolin (H-Arg-Tyr-Leu-Pro-Thr-OH) have been prepared, containing a single oxazole between Tyr and Pro and between Pro and Thr, respectively. A compound containing an oxazole moiety between Tyr and Pro and between Pro and Thr has also been prepare...

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Bibliographic Details
Published in:Organic letters 2001-11, Vol.3 (22), p.3427-3430
Main Authors: Plant, Andrew, Stieber, Frank, Scherkenbeck, Jürgen, Lösel, Peter, Dyker, Hubert
Format: Article
Language:English
Subjects:
Amides - chemistry
Animals
Digestive System - drug effects
Grasshoppers - chemistry
Grasshoppers - physiology
In Vitro Techniques
Indicators and Reagents
Muscle Contraction - drug effects
Neuropeptides - chemical synthesis
Neuropeptides - chemistry
Neuropeptides - pharmacology
Oligopeptides - chemical synthesis
Oligopeptides - chemistry
Oligopeptides - pharmacology
Oxazoles - chemical synthesis
Oxidation-Reduction
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Summary:Three oxazole analogues of the insect neuropeptide proctolin (H-Arg-Tyr-Leu-Pro-Thr-OH) have been prepared, containing a single oxazole between Tyr and Pro and between Pro and Thr, respectively. A compound containing an oxazole moiety between Tyr and Pro and between Pro and Thr has also been prepared. All compounds have been tested for myotropic activity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016269k