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Design and synthesis of a bicyclic non-peptide β-bend mimetic of enkephalin

✍ Scribed by Bruce L. Currie; John L. Krstenansky; Zhao-Lan Lin; Jiraporn Ungwitayatorn; Yu-Hwei Lee; Michelle del Rosario-Chow; Wen-Sing Sheu; Michael E. Johnson

Publisher
Elsevier Science
Year
1993
Tongue
French
Weight
781 KB
Volume
49
Category
Article
ISSN
0040-4020

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✦ Synopsis

hbrtmct: 9th~~ ~~~~~~'~~1 pvups of a biokgi~~ act& peptide can be mnqd on a non-pep&k framework in the "bkkgimlly act& wt,hnadon " it may be possible to maxrmiza the captor intrradios ad eliminate or r&a the mnbw of amide bonds that are atikbkfor pmteo&tk enzyme ckawtge. lhus, we han3 ~ig~~~~~~ the 2,5,7-~~~tit~~2,3.4,4a,7,7a~~~~,3-b~~k~g~~~ ads basis for mm-peptide mimetic analogs for pqvtides that prqfu the@ed m@nm&on. Computer assistexi mokcukr modeling studies haw indicateva' that the redting analogs cksdy rctemhk the fvnaiotml grorgp positioning parricufarly of type I and I' peptide &bends. Compktai adogs 5f Lcu-edephaiin have been synthesized and shown to be potent nakxo~-revwsibk agonists in tke ekctrical& stimulated guinea pig ikum assay. The b-bend, also known as a &turn, &loop or reversed turn, is a 1~~~ ~~1~~1~ Hbonded ring and is a conformational feature existing in many biologically active peptide and proteins. The main feature of a B-bend is the reversal of the direction of the peptide chain by approximately 180". Several types of B-bend ~nfo~ations were originally described by Vale in 1968.' By varying tpz, &, #3, &, there are at least 14 types of B-bend structure which have been tabulated by Chou and Rtsmar~.~ Among

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