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Neurologically active plant compounds and peptide hormones: a chirality connection
Author(s) -
Fraternali Franca,
Anselmi Claudio,
Temussi Piero Andrea
Publication year - 1999
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/s0014-5793(99)00244-6
Subject(s) - chirality (physics) , stereochemistry , moiety , peptide , chemistry , alkaloid , tyramine , conformational change , biochemistry , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
The most dramatic, but seldom mentioned, difference between alkaloid and peptide opioids is the change of chirality of the α carbon of the tyramine moiety. We propose that the presence of Gly 2 or d ‐Ala 2 in the two most common message domains compensates this change by allowing the attainment of unusual conformations. A thorough conformational search of Tyr‐ d ‐Ala‐Phe‐NH‐CH 3 and of its isomer Tyr‐ l ‐Ala‐Phe‐NH‐CH 3 backs this view and establishes a solid link between alkaloid and peptide opioids. This finding supports the notion that morphine, like other neurologically active plant compounds, may bind to endogenous receptors in plants to regulate cell‐to‐cell signaling systems.