Kinetic resolution of tropic acid ethyl ester and its derivatives by lipase PS

Atuu, Mary Rose; Mahmood, Syed Junaid; Laib, Frank; Hossain, M. Mahmun

doi:10.1016/j.tetasy.2004.08.013

Cited by 17 publications

(9 citation statements)

References 35 publications

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“…Carbon‐14–labeled tropic acid was reported before, although little or no details on the synthesis were given . The synthesis of unlabeled racemic and chiral tropic acid chemically or biosynthetically was also reported by several groups . Our preparation of carbon‐14–labeled racemic tropic acid provides access to both enantiomers of Buscopan, and a viable method of separating the enantiomers of tropic acid is developed.…”

Section: Resultsmentioning

confidence: 99%

“…10,11 The synthesis of unlabeled racemic and chiral tropic acid chemically or biosynthetically was also reported by several groups. [12][13][14][15][16][17][18][19][20] Our preparation of FIGURE 1 Chemical structures of Buscopan, Spiriva, scopoline, and scopolamine SCHEME 1 Synthesis of deuterium-and carbon-14-labeled Buscopan SCHEME 2 Synthesis of dl-tropic acid-[carboxyl- 14 C] carbon-14-labeled racemic tropic acid provides access to both enantiomers of Buscopan, and a viable method of separating the enantiomers of tropic acid is developed. The synthesis of racemic tropic acid (Scheme 2) started from benzyl bromide, which was converted to the nitrile (2) in water in the presence of potassium cyanide-14 C and tetrabutylammonium bromide.…”

Section: Resultsmentioning

confidence: 99%

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Buscopan labeled with carbon‐14 and deuterium

Latli

Stiasni

Hrapchak

et al. 2016

Labelled Comp Radiopharmac

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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- C bromide, and n-butyl- H 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.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Buscopan labeled with carbon‐14 and deuterium

Latli

Stiasni

Hrapchak

et al. 2016

Labelled Comp Radiopharmac

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“…12 Interestingly, another β-hydroxy acid of tropic acid attracts our attention, which can exist in natural compounds of hyoscyamine and hyoscine derived from natural plants of henbane and stramonium. 42,43 The C−H acidity of the chiral center of tropic acid should be weaker than that in mandelic acid due to replacing hydroxyl groups with hydroxymethyl groups bonded to chiral carbon centers. However, in the literature studies, the preparation of enantiopure tropic acid needs a resolution progress using enantiopure reagents or enzymes.…”

Section: ■ Introductionmentioning

confidence: 99%

Monomer-Promoting Asymmetric Kinetic Resolution-Alternating Copolymerization To Afford AAB-Type Copolyesters

Xian

et al. 2023

J. Am. Chem. Soc.

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Living copolymerization of mixed monomers can enrich the diversity of copolymer materials with well-defined performance via controlling both monomers and stereosequences. However, periodic sequence-controlled living copolymerization of same-type monomers with more than two components in synthetic polymer science remains a challenge. In this work, a new method of monomer-promoting asymmetric kinetic resolution-alternating copolymerization can let a tricomponent mixture of l-lactide (S,S-LA or l-LA) and two enantiomeric isomers of racemic tropic acid cyclic esters (tropicolactone) be polymerized into sequence-controlled −(ASASBS) n – type biodegradable copolyesters (the subscript S presents the configuration and A and B present lactic acid units and tropic acid units, respectively), and diblock copolymers of −(ASASBS) n -b-(ARARBR) n – can further be obtained upon addition of R,R-LA (d -LA). Compared to previous asymmetric kinetic resolutions of racemic chemicals via polymerization or organic reactions, no enantiopure catalyst/initiator is required in this system. After the resolution and alternating copolymerization of S,S-LA and rac-tropicolactone, the ee value of unreacted tropicolactone can reach 99.4%. The alternating probability between tropicolactone and lactide monomers is more than 96% in periodic sequence polymers of −(ASASBS) n –. The tetracomponent mixture of rac-lactide and rac-tropicolactone can be copolymerized into an alternating copolymer with a −((ASASBS) x -ran-(ARARBR) y ) n – structure, in which the stereoselective linkage probability of 95% after S,S-lactide (R,R-lactide) followed by S-tropicolactone (R-tropicolactone) keeps very high too.

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“…3.1.1.3) is one of the most important industrial enzymes that catalyze the hydrolysis and the synthesis of triglycerides or acyl and aryl esters at an oil−water interface. Interest in lipases has increased markedly in the past 2 decades owing to their wide applications in food (Pandey et al, 1999; Jennings and Akoh, 2001), chemical (Villeneuve et al, 2000; Berglund, 2001), and medical industries (Oades et al, 1995; Aronne, 1998), especially in the enzymatic resolution of chiral compounds (de Jesus et al, 1995; Nair and Joly, 2000; Atuu et al, 2004).…”

Section: Introductionmentioning

confidence: 99%

Enhanced Production of Penicillium expansum PED-03 Lipase through Control of Culture Conditions and Application of the Crude Enzyme in Kinetic Resolution of Racemic Allethrolone

Dai

Xia

2008

Biotechnol Progress

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Alkaline lipase production was performed in submerged fermentation by Penicillium expansum PED-03. It was found that the suitable carbon source and nitrogen source for lipase production were 0.5% starch and 4.0% soybean meal, respectively. The maximal lipase activity (850 U/mL) of production was achieved at initial pH 5.5-6.0, 26 degrees C, 72 h. Tween-80 was an effective enhancer for lipase production. Agitation speed of the fermentor played an important role, and the suitable agitation speed for lipase production was 500 r/min. The lipase was stable within the range of pH 7.0-10.0 and 20-40 degrees C, and the optimum conditions for the enzymatic reaction were 35 degrees C and pH 9.5. The enzymatic resolution of racemic allethrolone (4-hydroxy-3-methyl-2-(2-propenyl)-2- cyclopenten-1-one) was carried out by the lipase from P. expansum PED-03, and the conversion reached 48% with excellent enantioselectivity (E > 100), which showed a good application potential in the production of optically pure allethrolone.

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Kinetic resolution of tropic acid ethyl ester and its derivatives by lipase PS

Cited by 17 publications

References 35 publications

Buscopan labeled with carbon‐14 and deuterium

Buscopan labeled with carbon‐14 and deuterium

Monomer-Promoting Asymmetric Kinetic Resolution-Alternating Copolymerization To Afford AAB-Type Copolyesters

Enhanced Production of Penicillium expansum PED-03 Lipase through Control of Culture Conditions and Application of the Crude Enzyme in Kinetic Resolution of Racemic Allethrolone

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