
TY  - JOUR
A1  - Ball, JB 
A1  - Craik, DJ 
A1  - Alewood, PF 
A1  - Morrison, S 
A1  - Andrews, PR 
A1  - Nicholls, IA 
T1  - Synthesis and Conformational Analysis of the Slime-Mold Acrasin Glorin
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1989
VL  - 42
IS  - 12
SP  - 2171
EP  - 2180
KW  - 
UR  - https://doi.org/10.1071/CH9892171 
N2  - The chemotactic dipeptide for the slime-mould Polysphondylium violaceum, glorin (N- propionyl-y-L-glutamyl-L-ornithine-&#948;-lac ethyl ester) (8), was synthesized convergently in five steps with 41% overall yield, starting from L- ornithine hydrochloride (1) and L- glutamic acid &#947;-benzyl ester (4). -1H n.m.r. spectral analysis led to the conclusion that the propionamide and the &#947;-L- glutamyl amide bonds both undergo slow cis-trans isomerism in solution at room temperature. From a Karplus-type analysis of the values of the C&#945;,C&#946; coupling constants at the lactam chiral carbon, it was concluded that the six-membered ring can adopt either a half-chair or half-boat conformation, but it is not clear which. Similar calculations for the glutamyl Ca,C&#946; coupling constants were performed and, from these, significantly different relative populations for the three staggered conformations about the Glu-Ca,C&#946; bond were suggested. Receptor binding studies showed that glorin did not bind significantly to any of the six receptors studied, including opioid, dopamine, central benzodiazepine, peripheral benzodiazepine, &#945;1-adrenoceptor and &#945;2-adrenoceptor sites. 
ER  -

