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J Med Chem. 2007 Dec 27;50(26):6725-9. Epub 2007 Dec 1.

Allosteric modulation of the dopamine receptor by conformationally constrained type VI beta-turn peptidomimetics of Pro-Leu-Gly-NH2.

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  • 1Department of Medicinal Chemistry, University of Minnesota, Minneapolis 55455-0343, USA.


A peptidomimetic of Pro-Leu-Pro-NH2, 7, possessing an indolizidinone type VI beta-turn mimic was synthesized via improved high-yielding protocols for the preparation and Cbz protection of alpha-allylproline. Bicyclic peptidomimetic 7 and spirobicylic peptidomimetic 8 enhanced the binding of [3H] N-propylnorapomorphine to dopamine receptors indicating that a type VI beta-turn is a possible bioactive conformation of the homochiral Pro-Leu-Pro-NH2 and Pro-Pro-Pro-NH 2 analogues of Pro-Leu-Gly-NH2 at the dopamine receptor allosteric regulatory site.

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