To the problem of biologically active conformation of enkephalin
- PMID: 7231396
- DOI: 10.1007/BF02354848
To the problem of biologically active conformation of enkephalin
Abstract
A semi-rigid structural analog of [Leu5] enkephalin, possessing the azo-bridge between Tyr1 and Phe4 residues, was synthesized, along with two other linear enkephalin analogs: [4'-amino Phe4] enkephalin and [4'/hydroxyphenyl/-azo Phe4] enkephalin. The results of the determination of the analgesic activity of the synthesized compounds suggest that the biologically active conformation of the enkephalin molecule should be such that both aromatic rings, Tyr1 and Phe4, are situated in close proximity.
Similar articles
-
X-ray diffraction studies of enkephalins. Crystal structure of [(4'-bromo) Phe4,Leu5]enkephalin.Biochem J. 1984 Mar 15;218(3):677-89. doi: 10.1042/bj2180677. Biochem J. 1984. PMID: 6721829 Free PMC article.
-
A cyclic enkephalin analog with high in vitro opiate activity.Proc Natl Acad Sci U S A. 1980 Dec;77(12):7162-6. doi: 10.1073/pnas.77.12.7162. Proc Natl Acad Sci U S A. 1980. PMID: 6261242 Free PMC article.
-
A crystal molecular conformation of leucine-enkephalin related to the morphine molecule.Biopolymers. 1989 Jan;28(1):27-40. doi: 10.1002/bip.360280106. Biopolymers. 1989. PMID: 2720108
-
Melphalan-containing N,N-dialkylenkephalin analogs as potential irreversible antagonists of the delta opioid receptor.NIDA Res Monogr. 1986;75:185-8. NIDA Res Monogr. 1986. PMID: 2828969
-
[Structural-functional relations of short analogs of enkephalin].Bioorg Khim. 1986 Jul;12(7):869-97. Bioorg Khim. 1986. PMID: 3021174 Review. Russian.
Cited by
-
Applications of biaryl cyclization in the synthesis of cyclic enkephalin analogs with a highly restricted flexibility.Amino Acids. 2024 Mar 1;56(1):18. doi: 10.1007/s00726-023-03371-5. Amino Acids. 2024. PMID: 38427104 Free PMC article.
-
Design, synthesis, and opioid activity of arodyn analogs cyclized by ring-closing metathesis involving Tyr(allyl).Bioorg Med Chem. 2018 Mar 15;26(6):1157-1161. doi: 10.1016/j.bmc.2017.11.029. Epub 2017 Nov 21. Bioorg Med Chem. 2018. PMID: 29273415 Free PMC article.
-
Molecular-dynamics simulations of [Met5]- and [D-Ala2,Met5]-enkephalins. Biological implication of monomeric folded and dimeric unfolded conformations.Biochem J. 1988 Oct 15;255(2):621-8. Biochem J. 1988. PMID: 3202835 Free PMC article.
-
Synthesis of stable and potent delta/mu opioid peptides: analogues of H-Tyr-c[D-Cys-Gly-Phe-D-Cys]-OH by ring-closing metathesis.J Med Chem. 2007 Jun 28;50(13):3138-42. doi: 10.1021/jm061048b. Epub 2007 Jun 1. J Med Chem. 2007. PMID: 17539621 Free PMC article.