Enantiomeric preference of the butyrylcholinesterase toward chiral quinuclidinium esters and amides (CROSBI ID 498525)
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Podaci o odgovornosti
Primožič, Ines ; Odžak, Renata ; Tomić, Srđanka
engleski
Enantiomeric preference of the butyrylcholinesterase toward chiral quinuclidinium esters and amides
Quaternary N-benzyl (R)- and (S)-esters of quinuclidin-3-ol and amides of quinuclidin-3-yl amine and pivalic, butyric and benzoic acid were synthesized. Kinetic studies revealed that (R)-enantiomers of tested esters are much better substrates than (S)-enantiomers. On the other hand, (S)-enantiomers of esters and amides showed higher affinity toward BChE except in the case of the butyric acid derivatives. In order to explain experimental data concerning reactivity of enantiomers, quantum chemical calculations (ONIOM scheme, B3LYP/3-21G ; PM3) of the stable species in the acylation step were performed. It was shown that enantiomeric preference of BChE, as well as rates of hydrolysis, are governed in large part by steric limitations and electrostatic interactions in the choline subsite.
butyrylcholinesterase ; N-benzyl esters and amides
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Podaci o prilogu
x-x.
2004.
objavljeno
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VIII International Meeting on Cholinesterases
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Podaci o skupu
VIII International Meeting on Cholinesterases
poster
26.09.2004-30.09.2004
Perugia, Italija