Pregled bibliografske jedinice broj: 195362
Resolucija racemičnih N-kvaternih derivata kinuklidin-3-il-izobutirata butirilkolinesterazom
Resolucija racemičnih N-kvaternih derivata kinuklidin-3-il-izobutirata butirilkolinesterazom // XIX. hrvatski skup kemičara i kemijskih inženjera : Knjiga sažetaka / Škare, Danko (ur.).
Zagreb: HKD, HDKIT, 2005. str. 128-128 (poster, nije recenziran, sažetak, znanstveni)
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Naslov
Resolucija racemičnih N-kvaternih derivata kinuklidin-3-il-izobutirata butirilkolinesterazom
(Resolution of racemic N-quaternary derivatives of quinuclidin-3-yl isobutyrates by butyrylcholinesterase)
Autori
Oršulić, Mislav ; Primožič, Ines ; Tomić, Srđanka
Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni
Izvornik
XIX. hrvatski skup kemičara i kemijskih inženjera : Knjiga sažetaka
/ Škare, Danko - Zagreb : HKD, HDKIT, 2005, 128-128
Skup
XIX. hrvatski skup kemičara i kemijskih inženjera
Mjesto i datum
Opatija, Hrvatska, 24.04.2005. - 27.04.2005
Vrsta sudjelovanja
Poster
Vrsta recenzije
Nije recenziran
Ključne riječi
butirilkolinesteraza; esteri kinuklidin-3-ola
(butyrylcholinesterase; esters of quinuclidin-3-ol)
Sažetak
Many esters of optically active quinuclidin-3-ol have been tested and recognized as pharamacological agents. Previous work also showed that butyryl cholinesterase (BChE ; 3.1.1.8.) catalyzed the hydrolysis of N-benzyl protected quinuclidinium esters in a stereoselective manner. In order to study the influence of substrate structure on kinetic resolution, racemic, (R)- and (S)-esters of quinuclidin-3-ol and isobutyric acid were synthesized as well as their racemic and chiral, quaternary N-benzyl and N-p-bromobenzyl derivatives. Racemic quinuclidin-3-yl acetate was synthesized in the first step by esterification of quinuclidin-3-ol with acetic anhydride. Resolution of the racemate with L- and D-tartaric acid, enantiomerically pure acetates were obtained. Chiral (R)- and (S)-quinuclidin-3-ols were prepared by hydrolysis of (R)- and (S)-acetates, respectively. N-Benzyl and N-p-bromobenzyl derivatives were synthesized in the next step by quaternization of appropriate chiral or racemic esters with benzyl bromide and p-bromobenzyl bromide. The rates of hydrolysis were monitored (HPLC) at 30°C in 0.1 M phosphate buffer, pH 7.4. Kinetic studies revealed that (R)-enatiomers of the tested esters are much better substrates than (S)-enantiomers. Introduction of the bromine atom in the para position of the phenyl ring resulted in a remarkable improvement of hydrolysis enantioselectivity.
Izvorni jezik
Hrvatski
Znanstvena područja
Kemija
