The Studies on a new type of Enzymatic Dynamic Kinetic Resolution based on Esterification.

RYSZARD, OSTASZEWSKI (2017) The Studies on a new type of Enzymatic Dynamic Kinetic Resolution based on Esterification. In: Sixth International Conference on Advances in Applied Science and Environmental Technology - ASET 2017, 25-26 February 2017, Bangkok, Thailand.

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Chiral, β,γ-Unsaturated carboxylic acids derivatives are important intermediates in the synthesis of many biologically active compounds; for example anti-microtubule agents [1], Bisnorvernolepin [2] and Vineomycinone B2 [3]. Recently we have performed studies on enzymatic kinetic resolution based on esterification of carboxylic acids with orthoestres, used as a donor of alkoxy group [4,5]. As a compound for our studies, we choose 2-benzyl-2-methylbut-3-enic acid, which contains stereogenic quaternary carbon center. This compound is a substrate for the synthesis of irreversible inhibitors of a carboxypeptidase A, a representative zinc-containing proteolytic enzyme [6]. 2-Benzyl-2-methylbut-3-enic acid was synthesized in 4-step synthesis, containing enzymatic hydrolysis of benzylmethylmalonic dimethylester [6]. We propose short, two step synthesis of optically active 2-benzyl-2-methylbut-3-enic acid from commercially available tiglic acid. The results of optimization of the kinetic resolution of 2-benzyl-2-methylbut-3-enic acid, containing enzyme screening, influence of solvent and reaction conditions will be demonstrated.[7].

Item Type: Conference or Workshop Item (Paper)
Uncontrolled Keywords: [1] Hayashi, Y. et al. J. Org. Chem. 2000 65 8402-8405 [2] Kieczykowski G.R. et al. J. Am. Chem. Soc. 1980 102 782-790 [3] Danishefsky S.J. et al. J. Am. Chem. Soc. 1985 107 1285-1293 [4] Brodzka, A.; Koszelewski D.; Ostaszewski R. J. Mol. Catal. BEnzym. 2012 82 96-101 [5] Brodzka, A. et al. Tetrahedron-Assymetry 2013 8 427-433 [6] Lee, M.; Kim, D.H. Bioorgan. Med. Chem. 2002, 10, 913-922 [7] Ostaszewski R., et al. ACS Catal., 2016, 6, 3287−3292,
Depositing User: Mr. John Steve
Date Deposited: 16 Mar 2019 11:57
Last Modified: 16 Mar 2019 11:57

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