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Enzyme-catalyzed cascade synthesis of hydroxyiminoacetamides

Knežević, Anamarija; Vinković, Vladimir; Maraković, Nikola; Šinko, Goran (2014) Enzyme-catalyzed cascade synthesis of hydroxyiminoacetamides. Tetrahedron Letters, 55 (31). pp. 4338-4341. ISSN 0040-4039

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Abstract

In order to synthesize N-(3-azido-1- phenylpropyl)-2-hydroxyiminoacetamide, a key compound for the preparation of acetylcholinesterase (AChE) reactivators of the N- substituted 2-hydroxyiminoacetamide type, it was necessary to develop a method for forming an amide bond between an ethyl glyoxylate oxime and an amine. Using Candida antarctica lipase B (CAL-B) in a cascade enzyme-BOP catalyzed reaction, the efficient synthesis of the target hydroxyiminoacetamide was achieved.

Item Type: Article
Uncontrolled Keywords: amide formation; chemoenzymatic synthesis; coupling reagents; enzyme catalysis; oxime protecting groups
Subjects: NATURAL SCIENCES > Chemistry
NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Dizajn, sinteza i evaluacija novih protuotrova kod trovanja živčanim bojnim otrovima i pesticidima-CHOLINESTERASEZrinka KovarikIP-2013-11-4307HRZZ
Kiralni organski materijali – sintetska, strukturna i funkcionalna istraživanja-Vladimir Vinković098-0982904-2910MZOS
Depositing User: Anamarija Knežević
Date Deposited: 03 Nov 2017 12:51
Last Modified: 03 Nov 2017 12:51
URI: http://fulir.irb.hr/id/eprint/3660
DOI: 10.1016/j.tetlet.2014.06.027

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