Synthesis of (E)-α,β-unsaturated carboxylic esters derivatives from cyanoacetic acid via promiscuous enzyme-promoted cascade esterification/Knoevenagel reaction. 2019

Monika Wilk, and Damian Trzepizur, and Dominik Koszelewski, and Anna Brodzka, and Ryszard Ostaszewski
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

A new enzymatic protocol based on lipase-catalyzed cascade toward (E)-α,β-unsaturated carboxylic esters is presented. The proposed methodology consists of elementary organic processes starting from acetals and cyanoacetic acid leading to the formation of desired products in a cascade sequence. The combination of enzyme promiscuous abilities gives a new opportunity to synthesize complex molecules in the one-pot procedure. Results of studies on the influence of an enzyme type, solvent, and temperature on the cascade reaction course are reported. The presented methodology provides meaningful qualities such as significantly simplified process, excellent E-selectivity of obtained products and recycling of a biocatalyst.

UI MeSH Term Description Entries
D008049 Lipase An enzyme of the hydrolase class that catalyzes the reaction of triacylglycerol and water to yield diacylglycerol and a fatty acid anion. It is produced by glands on the tongue and by the pancreas and initiates the digestion of dietary fats. (From Dorland, 27th ed) EC 3.1.1.3. Triacylglycerol Lipase,Tributyrinase,Triglyceride Lipase,Acid Lipase,Acid Lipase A,Acid Lipase B,Acid Lipase I,Acid Lipase II,Exolipase,Monoester Lipase,Triacylglycerol Hydrolase,Triglyceridase,Triolean Hydrolase,Hydrolase, Triacylglycerol,Hydrolase, Triolean,Lipase A, Acid,Lipase B, Acid,Lipase I, Acid,Lipase II, Acid,Lipase, Acid,Lipase, Monoester,Lipase, Triglyceride
D002175 Candida A genus of yeast-like mitosporic Saccharomycetales fungi characterized by producing yeast cells, mycelia, pseudomycelia, and blastophores. It is commonly part of the normal flora of the skin, mouth, intestinal tract, and vagina, but can cause a variety of infections, including CANDIDIASIS; ONYCHOMYCOSIS; VULVOVAGINAL CANDIDIASIS; and CANDIDIASIS, ORAL (THRUSH). Candida guilliermondii var. nitratophila,Candida utilis,Cyberlindnera jadinii,Hansenula jadinii,Lindnera jadinii,Monilia,Pichia jadinii,Saccharomyces jadinii,Torula utilis,Torulopsis utilis,Monilias
D004951 Esterification The process of converting an acid into an alkyl or aryl derivative. Most frequently the process consists of the reaction of an acid with an alcohol in the presence of a trace of mineral acid as catalyst or the reaction of an acyl chloride with an alcohol. Esterification can also be accomplished by enzymatic processes. Esterifications
D004952 Esters Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water. Ester
D000085 Acetates Derivatives of ACETIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain the carboxymethane structure. Acetate,Acetic Acid Esters,Acetic Acids,Acids, Acetic,Esters, Acetic Acid
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D055162 Biocatalysis The facilitation of biochemical reactions with the aid of naturally occurring catalysts such as ENZYMES.
D060326 Chemistry Techniques, Synthetic Methods used for the chemical synthesis of compounds. Included under this heading are laboratory methods used to synthesize a variety of chemicals and drugs. Inorganic Synthesis,Inorganic Synthesis Methods,Inorganic Synthesis Techniques,Methods of Inorganic Synthesis,Methods of Organic Synthesis,Methods of Peptide Synthesis,Organic Synthesis,Organic Synthesis Methods,Organic Synthesis Techniques,Peptide Synthesis Methods,Peptide Synthesis Techniques,Peptide Synthesis, Synthetic,Synthetic Chemistry Techniques,Synthetic Peptide Synthesis,Chemistry Technique, Synthetic,Inorganic Syntheses,Inorganic Synthesis Method,Inorganic Synthesis Technique,Method, Inorganic Synthesis,Method, Organic Synthesis,Method, Peptide Synthesis,Methods, Inorganic Synthesis,Methods, Organic Synthesis,Methods, Peptide Synthesis,Organic Syntheses,Organic Synthesis Technique,Peptide Syntheses, Synthetic,Peptide Synthesis Method,Peptide Synthesis Technique,Syntheses, Inorganic,Syntheses, Organic,Syntheses, Synthetic Peptide,Synthesis Method, Inorganic,Synthesis Method, Peptide,Synthesis Methods, Inorganic,Synthesis Methods, Peptide,Synthesis Technique, Inorganic,Synthesis Technique, Organic,Synthesis Technique, Peptide,Synthesis Techniques, Inorganic,Synthesis Techniques, Organic,Synthesis Techniques, Peptide,Synthesis, Inorganic,Synthesis, Organic,Synthesis, Synthetic Peptide,Synthetic Chemistry Technique,Synthetic Peptide Syntheses,Technique, Inorganic Synthesis,Technique, Organic Synthesis,Technique, Peptide Synthesis,Technique, Synthetic Chemistry,Techniques, Inorganic Synthesis,Techniques, Organic Synthesis,Techniques, Peptide Synthesis,Techniques, Synthetic Chemistry

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