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

Ashish P. Vartak; Kevin Skoblenick; Nancy Thomas; Ram K. Mishra; Rodney L. Johnson

doi:10.1021/jm070895r

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

Ashish P. Vartak, Kevin Skoblenick, Nancy Thomas, Ram K. Mishra, Rodney L. Johnson

Medicinal Chemistry

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Abstract

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

Original language	English (US)
Pages (from-to)	6725-6729
Number of pages	5
Journal	Journal of medicinal chemistry
Volume	50
Issue number	26
DOIs	https://doi.org/10.1021/jm070895r
State	Published - Dec 27 2007

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AU - Thomas, Nancy

AU - Mishra, Ram K.

AU - Johnson, Rodney L.

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

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