Hydrogenolysis of N-Alkyl- and N-(2-Oxoalkyl)-quinuclidinium Salts

Adamski, R. J.; Hackney, Robert E.; Numajiri, Satoru; Spears, L. J.; Yen, Elizabeth

doi:10.1055/s-1973-22186

Cited by 3 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Resolution of racemic N-benzyl derivative can therefore be achieved by hydrolysis with BChE. Furthermore, N-benzyl groups can be removed by catalytic hydrogenation, [15] thus regenerating tertiary chiral quinuclidin-3-ols, which can serve as precursors for the synthesis of a variety of pharmacologically interesting analogues.…”

Section: Hydrolyses Kineticsmentioning

confidence: 99%

Stereoselective Hydrolysis of Quaternary Quinuclidinium Benzoates Catalyzed by Butyrylcholinesterase

et al. 2002

View full text Add to dashboard Cite

Four chiral, quaternary, N-methyl and N-benzyl derivatives of (R)-and (S)-quinuclidin-3-yl benzoates were synthesized and studied as substrates of horse serum butyrylcholinesterase (BChE). The k cat for the substrates decreased in the order (R)-N-methyl Ͼ (R)-N-benzyl (2.3-fold slower) ϾϾ (S)-Nmethyl (70.5-fold slower reaction), while for the (S)-N-benzyl ester inhibition of the enzyme was observed. The kinetics of inhibition (K a = 3.3 µM) indicated that binding to the catalytic site of BChE occurred. From the ratio of the k cat /K M values of both enantiomers an enantiomeric excess of 95% was calculated for N-methyl derivatives. Thus, BChE is suitable as a biocatalyst for the resolution of racemic quaternary quinu-

show abstract

Section: Hydrolyses Kineticsmentioning

confidence: 99%