137310-15-7Relevant academic research and scientific papers
Chemoenzymatic synthesis of both enantiomers of baclofen
Chenevert, Robert,Desjardins, Michel
, p. 4249 - 4250 (1991)
Both enantiomers of baclofen have been synthesized in five steps from 4-chlorocinnamic acid. The key step is the highly stereoselective enzymatic hydrolysis of dimethyl 3-(4-chlorophenyl)glutarate by chymotrypsin.
PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE 3-SUBSTITUTED GLUTARIC ACID MONOAMIDE
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Page/Page column 14, (2012/11/13)
The process for producing an optically active 3-substituted glutaric acid monoamide is characterized in comprising the step of precipitating the optically active 3-substituted glutaric acid monoamide by mixing an acid and a mixed liquid containing an optically active 3-substituted glutaric acid monoamide represented by the following formula (2): wherein * indicates an asymmetric carbon atom; R1 is a C1-8 alkyl group, a C2-8 alkenyl group, a C2-8 alkynyl group, a C4-20 aryl group or a C5-20 aralkyl group; and the alkyl group, the alkenyl group, the alkynyl group, the aryl group and the aralkyl group may have a substituent, a basic compound, water and an organic solvent.
Chirality holds the key for potent inhibition of the botulinum neurotoxin serotype a protease
Stowe, G. Neil,Silhar, Peter,Hixon, Mark S.,Silvaggi, Nicholas R.,Allen, Karen N.,Moe, Scott T.,Jacobson, Alan R.,Barbieri, Joseph T.,Janda, Kim D.
supporting information; experimental part, p. 756 - 759 (2010/04/05)
(Chemical Equetion Presentation) Botulinum neurotoxin serotype A (BoNT/A) is the most toxic protein known to man and also a bioterrorism agent. As defined by our previous research targeting the etiological agent responsible for BoNT/A intoxication, a protease, we now report on the asymmetric synthesis of four new BoNT/A inhibitors; the most potent of this series is roughly 2-fold more active than the best small molecule inhibitor currently known.
Chemoenzymatic enantioselective synthesis of baclofen
Chenevert,Desjardins
, p. 2312 - 2317 (2007/10/02)
We report two different chemoenzymatic enantioselective syntheses of baclofen based on the distinction between enantiotopic ester groups in compounds bearing a prochiral centre. In the first approach, the key step is the highly stereoselective enzymatic hydrolysis of dimethyl 3-(4-chlorophenyl)glutarate by chymotrypsin in an aqueous medium. In the second approach, the key step is the enzyme-catalyzed esterification of 2-(4-chlorophenyl)-1,3-propanediol by acetic anhydride in the presence of a lipase in an organic medium. We report two different chemoenzymatic enantioselective syntheses of baclofen based on the distinction between enantiotopic ester groups in compounds bearing a prochiral centre. In the first approach, the key step is the highly stereoselective enzymatic hydrolysis of dimethyl 3-(4-chlorophenyl)glutarate by chymotrypsin in an aqueous medium. In the second approach, the key step is the enzyme-catalyzed esterification of 2-(4-chlorophenyl)-1,3-propanediol by acetic anhydride in the presence of a lipase in an organic medium.
