Enzyme-catalyzed cascade synthesis of hydroxyiminoacetamides

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 ox...

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Published in:Tetrahedron Letters
Main Authors: Knežević, Anamarija, Vinković, Vladimir, Maraković, Nikola, Šinko, Goran
Format: Article in Journal/Newspaper
Language:Croatian
Published: Elsevier 2014
Subjects:
Online Access:http://fulir.irb.hr/3660/
http://fulir.irb.hr/3660/1/Tetr%20Lett%20postprint.pdf
http://www.sciencedirect.com/science/article/pii/S0040403914010065
https://doi.org/10.1016/j.tetlet.2014.06.027
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spelling ftrboskovicinst:oai:fulir.irb.hr:3660 2023-05-15T14:00:01+02:00 Enzyme-catalyzed cascade synthesis of hydroxyiminoacetamides Knežević, Anamarija Vinković, Vladimir Maraković, Nikola Šinko, Goran 2014 application/pdf http://fulir.irb.hr/3660/ http://fulir.irb.hr/3660/1/Tetr%20Lett%20postprint.pdf http://www.sciencedirect.com/science/article/pii/S0040403914010065 https://doi.org/10.1016/j.tetlet.2014.06.027 hr hrv Elsevier info:eu-repo/grantAgreement/HRZZ/IP/IP-2013-11-4307 info:eu-repo/grantAgreement/MZOS/ZP/098-0982904-2910 http://fulir.irb.hr/3660/ http://www.sciencedirect.com/science/article/pii/S0040403914010065 doi:10.1016/j.tetlet.2014.06.027 http://fulir.irb.hr/3660/1/Tetr%20Lett%20postprint.pdf info:eu-repo/semantics/openAccess Tetrahedron Letters Chemistry Organic Chemistry info:eu-repo/semantics/article 2014 ftrboskovicinst https://doi.org/10.1016/j.tetlet.2014.06.027 2022-07-08T13:10:34Z 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. Article in Journal/Newspaper Antarc* Antarctica Ruđer Bošković Institute Zagreb: Full-text Institutional Repository (FULIR) Tetrahedron Letters 55 31 4338 4341
institution Open Polar
collection Ruđer Bošković Institute Zagreb: Full-text Institutional Repository (FULIR)
op_collection_id ftrboskovicinst
language Croatian
topic Chemistry
Organic Chemistry
spellingShingle Chemistry
Organic Chemistry
Knežević, Anamarija
Vinković, Vladimir
Maraković, Nikola
Šinko, Goran
Enzyme-catalyzed cascade synthesis of hydroxyiminoacetamides
topic_facet Chemistry
Organic Chemistry
description 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.
format Article in Journal/Newspaper
author Knežević, Anamarija
Vinković, Vladimir
Maraković, Nikola
Šinko, Goran
author_facet Knežević, Anamarija
Vinković, Vladimir
Maraković, Nikola
Šinko, Goran
author_sort Knežević, Anamarija
title Enzyme-catalyzed cascade synthesis of hydroxyiminoacetamides
title_short Enzyme-catalyzed cascade synthesis of hydroxyiminoacetamides
title_full Enzyme-catalyzed cascade synthesis of hydroxyiminoacetamides
title_fullStr Enzyme-catalyzed cascade synthesis of hydroxyiminoacetamides
title_full_unstemmed Enzyme-catalyzed cascade synthesis of hydroxyiminoacetamides
title_sort enzyme-catalyzed cascade synthesis of hydroxyiminoacetamides
publisher Elsevier
publishDate 2014
url http://fulir.irb.hr/3660/
http://fulir.irb.hr/3660/1/Tetr%20Lett%20postprint.pdf
http://www.sciencedirect.com/science/article/pii/S0040403914010065
https://doi.org/10.1016/j.tetlet.2014.06.027
genre Antarc*
Antarctica
genre_facet Antarc*
Antarctica
op_source Tetrahedron Letters
op_relation info:eu-repo/grantAgreement/HRZZ/IP/IP-2013-11-4307
info:eu-repo/grantAgreement/MZOS/ZP/098-0982904-2910
http://fulir.irb.hr/3660/
http://www.sciencedirect.com/science/article/pii/S0040403914010065
doi:10.1016/j.tetlet.2014.06.027
http://fulir.irb.hr/3660/1/Tetr%20Lett%20postprint.pdf
op_rights info:eu-repo/semantics/openAccess
op_doi https://doi.org/10.1016/j.tetlet.2014.06.027
container_title Tetrahedron Letters
container_volume 55
container_issue 31
container_start_page 4338
op_container_end_page 4341
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