Abstract:
:We have previously proposed a model for the delta-opioid receptor binding conformation of the high affinity tetrapeptide Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13) based on experimental and theoretical conformational analysis of this peptide and a correlation of conformational preferences of further conformationally restricted analogues of this tetrapeptide with their receptor binding affinities. A key element of this model is the requirement that the Phe3 side chain exist in the chi 1 = -60 degrees conformation. Conformational calculations on the residue 3 dehydrophenylalanine analogues of JOM-13 suggest that while the dehydro (Z) phenylalanine analogue can be superimposed easily with the proposed binding conformer of JOM-13, the dehydro(E)phenylalanine analogue cannot. These results lead to the prediction that the dehydro(Z)phenylalanine analogue should display similar delta-receptor binding affinity as JOM-13 while the dehydro(E)phenylalanine analogue is expected to bind less avidly. Synthesis and subsequent opioid receptor binding analysis of the dehydrophenylalanine analogues of JOM-13 confirm these predictions, lending support to the delta-pharmacophore model.
journal_name
Biopolymersjournal_title
Biopolymersauthors
Mosberg HI,Dua RK,Pogozheva ID,Lomize ALdoi
10.1002/(sici)1097-0282(199609)39:3<287::aid-bip2>subject
Has Abstractpub_date
1996-09-01 00:00:00pages
287-96issue
3eissn
0006-3525issn
1097-0282pii
10.1002/(SICI)1097-0282(199609)39:3<287::AID-BIP2>journal_volume
39pub_type
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