Highly potent side-chain to side-chain cyclized enkephalin analogues containing a carbonyl bridge: Synthesis, biology and conformation

Journal of Peptide Science

Volumn 7, Issue 3, 2001, Pages 128-140

  Pawlak, Danuta ^a   Oleszczuk, Marta ^b   Wójcik, Jacek ^b   Pachulska, Maria ^a   Chung, Nga N ^c   Schiller, Peter W ^c   Izdebski, Jan ^a  

^a UNIVERSITY OF WARSAW   (Poland)

^b INSTITUTE OF BIOCHEMISTRY AND BIOPHYSICS   (Poland)

^c CLIN RESEARCH INSTITUTE OF MONTREAL   (Canada)

Author keywords

Conformation; Cyclic opioid peptides; EDMC; NMR; Side chain to side chain cyclization; Structure activity relationship; Synthesis

Indexed keywords

BIS(4 NITROPHENYL)CARBONATE; CARBONIC ACID DERIVATIVE; CARBONYL DERIVATIVE; CYCLOENKEPHALINAMIDE[N EPSILON,N BETA' CARBONYL 2 DEXTRO LYSINE 5 (ALPHA,BETA DIAMINOPROPIONIC ACID)]; ENKEPHALIN DERIVATIVE; ENKEPHALINAMIDE DERIVATIVE; LEUCINE ENKAPHALIN; MU OPIATE RECEPTOR AGONIST; OPIATE PEPTIDE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CHEMICAL COMPOSITION; CHEMICAL INTERACTION; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; CYCLIZATION; DRUG POTENCY; ELECTRICITY; GUINEA PIG; ILEUM; MOLECULAR BIOLOGY; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN INTERACTION; PROTEIN STRUCTURE; STRUCTURE ANALYSIS; SYSTEM ANALYSIS; VAS DEFERENS;

ANIMALS; CARBON; ENKEPHALINS; GUINEA PIGS; ILEUM; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MICE; MODELS, CHEMICAL; MODELS, MOLECULAR; MONTE CARLO METHOD; PEPTIDES; PROTEIN CONFORMATION; PROTONS; RECEPTORS, OPIOID, MU; VAS DEFERENS;

CAVIA PORCELLUS; SUS SCROFA;

EID: 0035060228     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/psc.303     Document Type: Article

References (36)

1. Conformational analysis of enkephalin and conformation-activity relationship
2. Synthesis of a novel side-chain to side-chain cyclized enkephalin analogue containing a carbonyl bridge
3. N-cyclohexyl-N′-isopropylcarbodiimide: A hybrid that combines the structural features of DCC and DIC
4. The action of morphine and related substances on contraction and on acetylcholine output of coaxially stimulated guinea pig ileum
5. A new example of a morphine sensitive neuroeffector junction
6. Unsulfated C-terminal 7-peptide of cholecystokinin: A new ligand of the opiate receptor
7. A cyclic enkephalin analog with high in vitro opiate activity
8. Opioid activities of fragments of β-endorphin and of its leucine65-analogue
9. Conformational analysis of a novel cyclic enkephalin analogue using NMR and EDMC calculations
10. Two-dimensional spectroscopy. Application to nuclear magnetic resonance
11. Enhanced NMR resolution by restricting the effective sample volume
12. Coherence transfer by isotropic mixing: Application to proton correlation spectroscopy
13. Structure determination of a tetrasaccharide: Transient nucleara overhauser effects in the rotating frame
14. Practical aspects of two-dimensional transverse NOE spectroscopy
15. Piure absorption gradient enhanced heteronuclear single quantum correlation spectroscopy with improved sensitivity
16. Sensitivity improvement in proton-detected two-dimensional heteronuclear correlation NMR spectroscopy
17. The sensitivity of experiments which use gradient pulses for coherence-pathway selection
18. A pure-phase homonuclear J-modulated HMQC experiment with tilted cross-peak patterns for an accuracy determination of homonuclear coupling constants
19. NMR chemical shifts of common laboratory solvents as trace impurities
20. 15N random coil NMR chemical shifts of the common amino acids. I. Investigations of nearest-neighbor effects
21. 2SO Solutions
22. Exploration of the conformational space of oxytocin and arginine-vasopressin using the electro-statistically driven Monte Carlo and molecular dynamics methods
23. On the multiple-minima problem in the conformational analysis of polypeptides. II. An electrostatically driven Monte Carlo method - Tests on poly{L-alanine}
24. On the multiple-minima problem in the conformational analysis of polypeptides. IV. Application of the electrostatically driven Monte Carlo method to the 20-residue membrane-bound portion of melittin
25. Energy parameters in polypeptides. 10. Improved geometrical parameters and nonbonded interactions for use in the ECEPP/3 algorithm, with application to proline-containing peptides
26. Empirical solvation models can be used to differentiate native from near-native conformations of bovine pancreatic trypsin inhibitor
27. Monte Carlo-minimization approach to the multiple-minima problem in protein folding
28. On the multiple-minima problem in the conformational analysis of polypeptides. I. Backbone degrees of freedom for a perturbed α-helix
29. Equation of state calculations by fast computing machines
30. On the evaluation of interproton distances for three-dimensional structure by NMR using a relaxation rate matrix analysis
31. An algorithm for least-squares estimation of nonlinear parameters
32. A novel side-chain-linked antiparallel cyclic dimer of enkephalin
33. MOLMOL: A program for display and analysis of macromolecular structures