Open AccessEnergy conformation study of Met-enkephalin and its D-Ala2 analogue and their resemblance to rigid opiates.
Author(s) -
Gilda H. Loew,
Stanley K. Burt
Publication year - 1978
Publication title -
proceedings of the national academy of sciences of the united states of america
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.011
H-Index - 771
eISSN - 1091-6490
pISSN - 0027-8424
DOI - 10.1073/pnas.75.1.7
Subject(s) - conformational isomerism , moiety , stereochemistry , phenethylamine , enkephalin , chemistry , residue (chemistry) , tyrosine , receptor , molecule , biochemistry , organic chemistry , opioid
Conformational similarities of Met-enkephalin and its D-Ala2 analogue to rigid opiates were studied by both empirical and quantum mechanical methods. By both methods, conformers with maximum resemblance to rigid opiates have the highest energies. Conformers with the lowest energy had no resemblance to rigid opiates. However, several low and intermediate energy conformers were identified in which at least the NH2-terminal tyrosine residue overlaps with the phenethylamine moiety of rigid opiates and which could equally well accommodate either Gly2 or D-Ala2. The conformer among these with greatest additional resemblance to other binding sites of rigid opiates is proposed as the most likely candidate for an induced fit at the receptor site.