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Croatica Chemica Acta, Vol.78 No.1 March 2005.

Original scientific paper

Enantiomers of Quinuclidin-3-ol Derivatives: Resolution and Interactions with Human Cholinesterases

Anita Bosak
Ines Primožić
Mislav Oršulić
Srdjanka Tomić
Vera Simeon-Rudolf

Fulltext: english, pdf (126 KB) pages 121-128 downloads: 614* cite
APA 6th Edition
Bosak, A., Primožić, I., Oršulić, M., Tomić, S. & Simeon-Rudolf, V. (2005). Enantiomers of Quinuclidin-3-ol Derivatives: Resolution and Interactions with Human Cholinesterases. Croatica Chemica Acta, 78 (1), 121-128. Retrieved from https://hrcak.srce.hr/2800
MLA 8th Edition
Bosak, Anita, et al. "Enantiomers of Quinuclidin-3-ol Derivatives: Resolution and Interactions with Human Cholinesterases." Croatica Chemica Acta, vol. 78, no. 1, 2005, pp. 121-128. https://hrcak.srce.hr/2800. Accessed 16 Dec. 2018.
Chicago 17th Edition
Bosak, Anita, Ines Primožić, Mislav Oršulić, Srdjanka Tomić and Vera Simeon-Rudolf. "Enantiomers of Quinuclidin-3-ol Derivatives: Resolution and Interactions with Human Cholinesterases." Croatica Chemica Acta 78, no. 1 (2005): 121-128. https://hrcak.srce.hr/2800
Harvard
Bosak, A., et al. (2005). 'Enantiomers of Quinuclidin-3-ol Derivatives: Resolution and Interactions with Human Cholinesterases', Croatica Chemica Acta, 78(1), pp. 121-128. Available at: https://hrcak.srce.hr/2800 (Accessed 16 December 2018)
Vancouver
Bosak A, Primožić I, Oršulić M, Tomić S, Simeon-Rudolf V. Enantiomers of Quinuclidin-3-ol Derivatives: Resolution and Interactions with Human Cholinesterases. Croatica Chemica Acta [Internet]. 2005 [cited 2018 December 16];78(1):121-128. Available from: https://hrcak.srce.hr/2800
IEEE
A. Bosak, I. Primožić, M. Oršulić, S. Tomić and V. Simeon-Rudolf, "Enantiomers of Quinuclidin-3-ol Derivatives: Resolution and Interactions with Human Cholinesterases", Croatica Chemica Acta, vol.78, no. 1, pp. 121-128, 2005. [Online]. Available: https://hrcak.srce.hr/2800. [Accessed: 16 December 2018]

Abstracts
The (R)- and (S)-enantiomers of quinuclidin-3-ol and quinuclidin-3-yl acetate as well as their quaternary N-methyl and N-benzyl derivatives were synthesized in order to study the stereoselectivity of human erythrocyte acetylcholinesterase (EC 3.1.1.7) and plasma butyrylcholinesterase (EC 3.1.1.8). The compounds were tested as substrates and inhibitors of cholinesterases. Both cholinesterases hydrolyze the derivatives of quinuclidin-3-yl acetate with a preference for the (R)- over (S)-enantiomers. In contrast to the hydrolysis of the enantiomers of acetates, the inhibition of acetylcholinesterase and butyrylcholinesterase by the (R)- and (S)-enantiomers of quinuclidin-3-ol derivatives does not reveal enantiomeric preference of the enzymes. The (R)- and (S)-acetates also act as nonstereoselective inhibitors of the enzyme-induced hydrolysis of acetylthiocholine. The best substrate is (R)-N-methyl-3-acetoxyquinuclidinium iodide with kcat = 1.5 x 106 min–1 and kcat = 5.5 x 104 min–1 for acetylcholinesterase and butyrylcholinesterase, respectively. The (R)- and (S)-N-benzylquinuclidinium derivatives are the most potent inhibitors of both enzymes.

Keywords
acetylcholinesterase; butyrylcholinesterase; chiral substrates and inhibitors; chiral quinuclidin-3-ol derivatives; chiral quinuclidin-3-yl acetates; stereoselectivity of cholinesterases

Hrčak ID: 2800

URI
https://hrcak.srce.hr/2800

[croatian]

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