221285-92-3Relevant academic research and scientific papers
The total synthesis and reassignment of stereochemistry of dragonamide
Chen, Hongliang,Feng, Yaqing,Xu, Zhengshuang,Ye, Tao
, p. 11132 - 11140 (2005)
The first total synthesis of dragonamide is reported. The synthesis has led to a reassignment of the configuration at the stereogenic centre on the alkyne-bearing fragment of the molecule.
Structural prerequisites for receptor binding of helicokinin I, a diuretic insect neuropeptide from helicoverpa zea
Van, Chien Tran,Zdobinsky, Tino,Seebohm, Guiscard,Nennstiel, Dirk,Zerbe, Oliver,Scherkenbeck, Juergen
, p. 2714 - 2725 (2014/05/06)
In insects essential physiological processes such as muscle activity or water balance are controlled by neuropeptides. However, owing to their metabolic instability and adverse physicochemical properties peptides are unsuited as crop protection agents. Helicokinin I, a diuretic neuropeptide of cotton pest Helicoverpa zea represents a most promising target for the design of neuropeptide mimetics. Several helicokinin analogues containing scaffolds with varying rigidity and different orientations of the N- and C-terminal peptide chains were synthesized and tested for receptor binding. Additional conformational analyses by NMR spectroscopy in a membrane-mimicking environment together with MD simulations provide a deeper insight into the structural requirements for receptor binding and explain the remarkable activity of a macrocyclic helicokinin I derivative. A delicate balance of rigidity and flexibility makes the difference between activity and inactivity. Detailed conformational studies of analogues of the diuretic insect-neuropeptide helicokinin I containing diverse cyclic scaffolds with different flexibility and orientation of the N- and C-termini provide a better understanding of the structural requirements for receptor binding. Copyright
