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Enantiomeric preference of the butyrylcholinesterase toward chiral quinuclidinium esters and amides (CROSBI ID 498525)

Prilog sa skupa u zborniku | sažetak izlaganja sa skupa

Primožič, Ines ; Odžak, Renata ; Tomić, Srđanka Enantiomeric preference of the butyrylcholinesterase toward chiral quinuclidinium esters and amides // VIII International Meeting on Cholinesterases. Perugia, 2004. str. x-x

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

Podaci o matičnoj publikaciji

VIII International Meeting on Cholinesterases

Perugia:

Podaci o skupu

VIII International Meeting on Cholinesterases

poster

26.09.2004-30.09.2004

Perugia, Italija

Povezanost rada

Kemija