124917-17-5Relevant articles and documents
The Assignment of the Absolute Configuration of β-Chiral Primary Alcohols with Axially Chiral Trifluoromethylbenzimidazolylbenzoic Acid
Kriegelstein, Michal,Profous, David,P?ibylka, Adam,Canka?, Petr
, p. 12912 - 12921 (2020)
Axially chiral trifluoromethylbenzimidazolylbenzoic acid (TBBA) was used as a chiral derivatization agent for the assignment of the absolute configuration of β-chiral primary alcohols. The structures varied from simple aliphatic alcohols to complex cyclic systems and highly substituted sugar derivatives. The NMR-based method was successfully implemented to evaluate 17 compounds and displayed ΔδPM values higher than 0.1 ppm in most cases, which makes TBBA superior to MTPA and MPA and comparable to 9-AMA.
Total Synthesis of (±)-Scopolamine: Challenges of the Tropane Ring
Nocquet, Pierre-Antoine,Opatz, Till
, p. 1156 - 1164 (2016)
Scopolamine was synthesized using 6,7-dehydrotropine as a key intermediate. Rhodium-catalyzed [4 + 3] cycloaddition chemistry and a modified Robinson-Sch?pf reaction were each independently evaluated for their utility in constructing the tropane core. Both synthetic approaches gave comparable overall yields.
Buscopan labeled with carbon-14 and deuterium
Latli, Bachir,Stiasni, Michael,Hrapchak, Matt,Li, Zhibin,Grinberg, Nelu,Lee, Heewon,Busacca, Carl A.,Senanayake, Chris H.
, p. 557 - 564 (2016/11/23)
Hyosine butyl bromide, the active ingredient in Buscopan, is an anticholinergic and antimuscarinic drug used to treat pain and discomfort caused by abdominal cramps. A straightforward synthesis of carbon-14– and deuterium-labeled Buscopan was developed using scopolamine, n-butyl-1-14C bromide, and n-butyl-2H9 bromide, respectively. In a second carbon-14 synthesis, the radioactive carbon was incorporated in the tropic acid moiety to follow its metabolism. Herein, we describe the detailed preparations of carbon-14– and deuterium-labeled Buscopan.
Functional characterization of recombinant hyoscyamine 6β-hydroxylase from Atropa belladonna
Li, Jing,Van Belkum, Marco J.,Vederas, John C.
experimental part, p. 4356 - 4363 (2012/08/28)
(-)-Hyoscyamine, the enantiomerically pure form of atropine, and its derivative scopolamine are tropane alkaloids that are extensively used in medicine. Hyoscyamine 6β-hydroxylase (H6H, EC 1.14.11.11), a monomeric α-ketoglutarate dependent dioxygenase, converts (-)-hyoscyamine to its 6,7-epoxy derivative, scopolamine, in two sequential steps. In this study, H6H of Atropa belladonna (AbH6H) was cloned, heterologously expressed in Escherichia coli, purified and characterized. The catalytic efficiency of AbH6H, especially for the second oxidation, was found to be low, and this may be one of the reasons why Atropa belladonna produces less scopolamine than other species in the same family. 6,7-Dehydrohyoscyamine, a potential precursor for the last step of epoxidation, was shown not to be an obligatory intermediate in the biosynthesis of scopolamine using purified AbH6H with an in vitro 18O labeling experiment. Moreover, the nitrogen atom in the tropane ring of (-)-hyoscyamine was found to play an important role in substrate recognition.
