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Synthesis of a novel side‐chain to side‐chain cyclized enkephalin analogue containing a carbonyl bridge
Author(s) -
Pawlak Danuta,
Chung Ngoc Nga,
Schiller Peter W.,
Izdebski Jan
Publication year - 1997
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/(sici)1099-1387(199707)3:4<277::aid-psc107>3.0.co;2-3
Subject(s) - side chain , bridge (graph theory) , chemistry , chain (unit) , enkephalin , stereochemistry , combinatorial chemistry , biochemistry , organic chemistry , medicine , opioid , anatomy , polymer , physics , receptor , astronomy
A novel type of cyclic opiod peptide analogue, cyclo( N ϵ , N ϵ′ ‐carbonyl‐ D ‐Lys 2 ,Lys 5 )enkephalinamide, was prepared from a linear precursor peptide. The peptide was synthesized on the Merrifield resin and also by a combination of the solid‐phase technique and the classical method in solution. In both cases the cyclization was performed by reaction of bis(4‐nitrophenyl)carbonate with the free side‐chain amino groups of the two lysine residues. The described method permits the convenient preparation of novel peptide analogues cyclized via a ureido group incorporating the side‐chain amino groups of two α,ω‐diamino acid residues. The cyclic enkephalin analogue containing a 21‐membered ring structure showed preference for μ over δ opioid receptors in opioid bioassays in vitro . © 1997 European Peptide Society and John Wiley & Sons, Ltd.