Synthetic Strategy toward γ-Keto Nitriles and Their Biocatalytic Conversion to Asymmetric γ-Lactones

Autor:	Brent D. Feske, Laura A. Wright, Richard Watkins, Ramon C. Hartage, Blair A. Weaver, Giuseppe Gumina, Sarah E. Franz, Ion Ghiviriga
Rok vydání:	2013
Předmět:	chemistry.chemical_classification Short-chain dehydrogenase Chemistry Aryl Organic Chemistry Intramolecular cyclization Enantioselective synthesis Combinatorial chemistry Catalysis Enzyme catalysis Hydrolysis chemistry.chemical_compound Enzyme Alkyl
Zdroj:	Synthesis. 45:2171-2178
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0033-1339282
Popis:	Asymmetric γ-hydroxy nitriles are valuable intermediates because hydrolysis of the nitriles can result in an intramolecular cyclization to chiral γ-lactones, which have a variety of biological uses. Starting with an assortment of different aldehydes (alkyl and aryl) a 4-step synthesis of γ-keto nitriles was developed. These prochiral substrates were then screened against a library of ketoreductases for their ability to stereoselectively reduce the carbonyl. Enzymes from the short chain dehydrogenase family showed activity and these enzymatic reactions were scaled up to produce a diverse set of chiral γ-lactones.
Databáze:	OpenAIRE
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