Development of a model for the δ-opioid receptor pharmacophore. 4. Residue 3 dehydrophenylalanine analogues of Tyr-c[ D -Cys-Phe- D -Pen]OH (JOM-13) confirm required gauche orientation of aromatic side chain
dc.contributor.author | Mosberg, Henry I. | en_US |
dc.contributor.author | Dua, Rajesh K. | en_US |
dc.contributor.author | Pogozheva, Irina D. | en_US |
dc.contributor.author | Lomize, Andrei L. | en_US |
dc.date.accessioned | 2006-04-28T16:28:39Z | |
dc.date.available | 2006-04-28T16:28:39Z | |
dc.date.issued | 1996-09 | en_US |
dc.identifier.citation | Mosberg, Henry I.; Dua, Rajesh K.; Pogozheva, Irina D.; Lomize, Andrei L. (1996)."Development of a model for the δ-opioid receptor pharmacophore. 4. Residue 3 dehydrophenylalanine analogues of Tyr-c[ D -Cys-Phe- D -Pen]OH (JOM-13) confirm required gauche orientation of aromatic side chain." Biopolymers 39(3): 287-296. <http://hdl.handle.net/2027.42/37870> | en_US |
dc.identifier.issn | 0006-3525 | en_US |
dc.identifier.issn | 1097-0282 | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/37870 | |
dc.identifier.uri | http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=retrieve&db=pubmed&list_uids=8756510&dopt=citation | en_US |
dc.description.abstract | We have previously proposed a model for the δ-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 Phe 3 side chain exist in the x 1 = −60° 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 δ-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 δ-pharmacophore model. © 1996 John Wiley & Sons, Inc. | en_US |
dc.format.extent | 778993 bytes | |
dc.format.extent | 3118 bytes | |
dc.format.mimetype | application/pdf | |
dc.format.mimetype | text/plain | |
dc.language.iso | en_US | |
dc.publisher | Wiley Subscription Services, Inc., A Wiley Company | en_US |
dc.subject.other | Chemistry | en_US |
dc.subject.other | Polymer and Materials Science | en_US |
dc.title | Development of a model for the δ-opioid receptor pharmacophore. 4. Residue 3 dehydrophenylalanine analogues of Tyr-c[ D -Cys-Phe- D -Pen]OH (JOM-13) confirm required gauche orientation of aromatic side chain | en_US |
dc.type | Article | en_US |
dc.rights.robots | IndexNoFollow | en_US |
dc.subject.hlbsecondlevel | Chemical Engineering | en_US |
dc.subject.hlbsecondlevel | Chemistry | en_US |
dc.subject.hlbsecondlevel | Materials Science and Engineering | en_US |
dc.subject.hlbtoplevel | Engineering | en_US |
dc.subject.hlbtoplevel | Science | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.contributor.affiliationum | College of Pharmacy, University of Michigan, Ann Arbor, MI 48109-1065 ; College of Pharmacy, University of Michigan, Ann Arbor, MI 48109-1065 | en_US |
dc.contributor.affiliationum | College of Pharmacy, University of Michigan, Ann Arbor, MI 48109-1065 | en_US |
dc.contributor.affiliationum | College of Pharmacy, University of Michigan, Ann Arbor, MI 48109-1065 | en_US |
dc.contributor.affiliationum | College of Pharmacy, University of Michigan, Ann Arbor, MI 48109-1065 | en_US |
dc.identifier.pmid | 8756510 | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/37870/1/2_ftp.pdf | en_US |
dc.identifier.doi | http://dx.doi.org/10.1002/(SICI)1097-0282(199609)39:3<287::AID-BIP2>3.0.CO;2-K | en_US |
dc.identifier.source | Biopolymers | en_US |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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