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

Preview

PDF - Accepted Version - article Download (427kB) | Preview

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 title Project leader Project code Project type Dizajn, sinteza i evaluacija novih protuotrova kod trovanja živčanim bojnim otrovima i pesticidima-CHOLINESTERASE Zrinka Kovarik IP-2013-11-4307 HRZZ Kiralni organski materijali – sintetska, strukturna i funkcionalna istraživanja- Vladimir Vinković 098-0982904-2910 MZOS
Depositing User:	Anamarija Knežević
Date Deposited:	03 Nov 2017 12:51
URI:	http://fulir.irb.hr/id/eprint/3660
DOI:	10.1016/j.tetlet.2014.06.027

Actions (login required)

View Item