Synthesis of Oleoylethanolamide Using Lipase

An effective process for the enzymatic synthesis of oleoylethanolamide is described in this study. The process included purification of a commercial oleic acid product and then optimization of the reaction between the purified oleic acid and ethanolamine in the presence of hexane and a lipase. Under the optimal amidation reaction conditions identified, oleoylethanolamide was obtained with 96.6% purity. The synthesis was also conducted on a large scale (50 mmol of each of the reactants), and oleoylethanolamide purity and yield after crystallization purification were 96.1 and 73.5%, respectively. Compared to the previous studies, the current method of preparing high-purity oleoylethanolamide is more effective and economically feasible. The scalability and ease for such synthesis make it possible to study the biological and nutritional functions of the cannabinoid-like oleoylethanolamide in animal or human subjects

New potential inhibitors of pheromonal attraction in the oriental fruit moth, Cydia molesta

New analogues of (Z)-dodec-8-en-1-yl acetate (Z8-12:OAc, 1), the main sex pheromone component of the Oriental fruit moth, Cydia molesta, were designed by formally transferring the terminal propyl group from the C-9 to the C-7 position to form vinyl-branched (2, 3) or, after isomerization, ethylidene-branched 4) structures and by replacing the -CH=CH- grouping by the -S-CH2- moiety (5, 6). Their biological activities were studied both electrophysiologically and behaviourally (laboratory mating and wind tunnel experiments). All the structural modifications resulted in analogues whose electroantennographic activities were lower than that of 1 following the order 1 much greater than 6 approximate to 5 much greater than 2 approximate to 4 approximate to 3. The single sensillum recording activities indicated that all the analogues stimulate the same Z8-12:OAc receptor neurone, In behavioural experiments, the analogues were generally found to reduce the ability of males to find a pheromone source, however, to different degrees. The highest inhibitory effect (90%) was observed for the thia analogues 5 and 6. The results support the view that the inhibitory properties of the analogues should not be entirely associated with their pheromone-mimicking capabilities

New mimics of the acetate function in pheromone-based attraction

Several analogues of (Z)-8-dodecenyl acetate (la), the major pheromone component of the Oriental fruit moth, Cydia molesta, with chloroformate and lactone functional groups in place of the acetate moiety, were synthesized and investigated for their biological activity at four evaluation levels, i.e. by electroantennography (EAG), electrosensillography (ESG), short-range sexual stimulation and activation in the flight-tunnel. We found very strict requirements on the shape as well as on the electron distribution of the acetate group for a productive interaction with the receptor. The behavioral results showed that, among the analogues investigated, the chloroformate lb, alken-4-olide 2a and also dodecyl acetate (lc) possess significant (60-85%) inhibitory activities. Based on electrophysiological evidence demonstrating that (i) only lb is competing with the major pheromone component la for the same receptor sites on the male antennal sensilla, (ii) lc elicits moderate EAG but no ESG responses and (iii) 2a does not produce any electrophysiologicai response at all, three possible inhibitory mechanisms by which these analogues are acting could be distinguished

Biotransformations of gamma-methyl-beta-ketosulfones:stereoselectivity of 3-methyl-1-(phenylsulfonyl)hexan-2-one reductions by various yeasts

The stereoselectivity of the reduction of rac-3-methyl1-(phenylsulfonyl)hexan-2-one (1) to 3-methyl1-(phenylsulfonyl)hexan-2-ol (2) diastereomers by more than 20 yeasts was studied. Reduction of carbonyl group in 1 proceeds with a high Re-face enantioselectivity: Candida guillermondii (98.9% e.e.), C. zeylanoides (>99.9%), and Kloeckera apiculata (99.6%), respectively and the (R)-1 enantiomer usually reacted faster. The enantioselectivity was determined by GC on chiral cyclodextrine phases and absolute configurations of products were assigned by NMR spectroscopy and a chemical correlation. Copyright (C) 1996 Elsevier Science Lt

Interactive visualization, information sharing, planning and learning for a team of robots

Abstract — In this paper we are interested in intelligent real-world multiagent systems that try to cooperatively solve a task. A multiagent (or multi-robot) system is a collection of agents that coexist in an environment and interact with each other. In our case, we are interested in fully cooperative multi-robot systems in which all robots share a common goal. We report in this work on research on the following topics: First, we developed a shared world model which estimates the global positions of objects in order to reduce the uncertainty in the environment. It allows us to fuse observations made by different agents and improve position estimates of each agent. Second, we extended our visualization of a robot soccer game by incorporating sensor data generated by a set of virtual sensors and by enabling remote human interaction. Third, we developed a new POMDP algorithm for agent planning in uncertain environments, in which the agent only receives partial information (through its sensors) regarding the true state of environment. Fourth, we have proposed a multiagent Q-learning technique, that allows a group of agents to learn how to jointly solve a task given the global coordination requirements of the system. I