Neurologically active plant compounds and peptide hormones: a chirality connection.
The most dramatic, but seldom mentioned, difference between alkaloid and peptide opioids is the change of chirality of the alpha carbon of the tyramine moiety. We propose that the presence of Gly2 or D-Ala2 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-CH3 and of its isomer Tyr-L-Ala-Phe-NH-CH3 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.
Fraternali
F
F
Division of Molecular Structure, National Institute for Medical Research, MRC, London, UK. ffranca@nimr.mrc.ac.uk
Anselmi
C
C
Temussi
P A
PA
D000596:Amino Acids / Q000737:chemistry; D006728:Hormones / Q000737:chemistry*; D008958:Models, Molecular; D010111:Oxymorphone / Q000031:analogs & derivatives / Q000737:chemistry; D010940:Plant Proteins / Q000737:chemistry*; D011487:Protein Conformation; D013141:Spiro Compounds / Q000737:chemistry
D000596:Amino Acids; D006728:Hormones; D010940:Plant Proteins; D013141:Spiro Compounds; C082822:7-spiroindanyloxymorphone; D010111:Oxymorphone