Newendomorphin-2(EM-2)analoguesincorporating(Z)-R,β-didehydrophenylalanine(Δ Phe)in placeofthenativephenylalanineinEM-2arereported.Tyr-Pro-ΔZPhe-Phe-NH2 {[ΔZPhe 3 ]EM-2}(1), Tyr-Pro-Phe-ΔZ Phe-NH2 {[ΔZ Phe 4 ]EM-2}(2),andTyr-Pro-ΔZ Phe-ΔZ Phe-NH2 {[ΔZ Phe 3,4 ]EM-2}(3) havebeensynthesized,theiropioidreceptorbindingaffinitiesandtissuebioassayactivitieswere determined,andtheirconformationalpropertieswereexamined.Compound 2 showshigh μ opioid receptorselectivityand μ agonistactivitycomparabletothoseofthenativepeptide.Theconformation adoptedinsolutionandinthecrystalby N-Boc-Tyr-Pro-ΔZPhe-Phe-NH2 (8)isreported.
Synthesis and evaluation of new endomorphin-2 analogues containing (Z)-α,β-didehydrophenylalanine (δZPhe) residues
MOLLICA, ADRIANO;PINNEN, Francesco Enrico;FELICIANI, FEDERICA;
2010-01-01
Abstract
Newendomorphin-2(EM-2)analoguesincorporating(Z)-R,β-didehydrophenylalanine(Δ Phe)in placeofthenativephenylalanineinEM-2arereported.Tyr-Pro-ΔZPhe-Phe-NH2 {[ΔZPhe 3 ]EM-2}(1), Tyr-Pro-Phe-ΔZ Phe-NH2 {[ΔZ Phe 4 ]EM-2}(2),andTyr-Pro-ΔZ Phe-ΔZ Phe-NH2 {[ΔZ Phe 3,4 ]EM-2}(3) havebeensynthesized,theiropioidreceptorbindingaffinitiesandtissuebioassayactivitieswere determined,andtheirconformationalpropertieswereexamined.Compound 2 showshigh μ opioid receptorselectivityand μ agonistactivitycomparabletothoseofthenativepeptide.Theconformation adoptedinsolutionandinthecrystalby N-Boc-Tyr-Pro-ΔZPhe-Phe-NH2 (8)isreported.File in questo prodotto:
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