Biocatalytic enantioselective synthesis of cenobamate, an antiepileptic drug

被引：1

作者：

Haritha, Vennapusa ^{[1
,2
]}

Deepthi, Pulivarthi ^{[2
]}

Gundamalla, Rachel ^{[2
]}

Nagesh, Kommu ^{[2
]}

Satyanarayana, Suggala V. ^{[3
]}

Rao, Adari Bhaskar ^{[2
]}

Balasubramanian, Sridhar ^{[4
]}

Reddy, Basireddy Venkata Subba ^{[2
]}

机构：

[1] Jawaharlal Nehru Technol Univ Anantapur, Ananthapuramu, India

[2] CSIR Indian Inst Chem Technol, Fluoro Agrochem, Hyderabad, India

[3] Jawaharlal Nehru Technol Univ Anantapur, JNTUA Coll Engn, Dept Chem Engn, Constituent Coll, Ananthapuramu, India

[4] CSIR Indian Inst Chem Technol, Ctr X Ray Crystallog, Hyderabad 500007, India

来源：

CHIRALITY | 2024年 / 36卷 / 04期

关键词：

biocatalysis; carrots; chiral alcohol; epilepsy; prochiral ketones; STEREOSELECTIVE REDUCTION; CHIRAL ALCOHOLS; PROGRESS REPORT; KETONES; VEGETABLES; ROOT;

D O I：

10.1002/chir.23660

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A green and efficient process for the synthesis of cenobamate has been accomplished in 70% yield and >99% ee through the bio-reduction of beta-ketotetrazole using Daucus carota whole plant cells. The corresponding beta-hydroxytetrazole was isolated in 60% yield and >98% ee. This is the first report on the biocatalytic reduction of beta-ketotetrazole using plant enzymes derived from D. carota root cells with excellent enantioselectivity.

引用

页数：7

共 50 条

[11] Synthetic Approaches toward the Synthesis of Brivaracetam: An Antiepileptic Drug
Gayke, Manoj
Narode, Hanuman
Eppa, Gyanchander
Bhosale, Rajesh S.
Yadav, Jhillu Singh
ACS OMEGA, 2022, 7 (03): : 2486 - 2503
[12] An Efficient Biocatalytic Preparation of a Key Chiral Intermediate to the Anti-Epileptic Drug Cenobamate Using an In-House Recombinant Alcohol Dehydrogenase
Assaf, Camille
Kurmis, Karolis
Wimsey, Christopher Thomas
Reddy, Dwarampudi Adi
Madhra, Mukesh Kumar
Bycroft, Matthew
CHEMISTRYSELECT, 2024, 9 (18):
[13] Enantioselective Biocatalytic Oxidative Desymmetrization of Substituted Pyrrolidines
Koehler, Valentin
Bailey, Kevin R.
Znabet, Anass
Raftery, James
Helliwell, Madeleine
Turner, Nicholas J.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (12) : 2182 - 2184
[14] Retigabine: the newer potential antiepileptic drug
Czuczwar, Piotr
Wojtak, Agnieszka
Cioczek-Czuczwar, Anna
Parada-Turska, Jolanta
Maciejewski, Ryszard
Czuczwar, Stanislaw J.
PHARMACOLOGICAL REPORTS, 2010, 62 (02) : 211 - 219
[15] Cordyceps fungus-mediated enantioselective synthesis of chiral alcohol and enhanced biocatalytic efficiency in cyclodextrin/surfactant-buffer system
Gui, Qian
Zhang, Hai -Min
Qian, Feng
Liu, Han -Yu
Kong, Xiang-Xin
Lv, Guo-Ying
Wang, Pu
BIOCHEMICAL ENGINEERING JOURNAL, 2024, 205
[16] Cyanide-free Enantioselective Synthesis of Nitriles: Synthetic Proof of a Biocatalytic Concept and Mechanistic Insights
Metzner, Richard
Okazaki, Seiji
Asano, Yasuhisa
Groeger, Harald
CHEMCATCHEM, 2014, 6 (11) : 3105 - 3109
[17] Sustainable biocatalytic synthesis of L-homophenylalanine as pharmaceutical drug precursor
Ahmad, A. L.
Oh, P. C.
Shukor, S. R. Abd
BIOTECHNOLOGY ADVANCES, 2009, 27 (03) : 286 - 296
[18] Biocatalytic Desymmetrization of an Atropisomer with both an Enantioselective Oxidase and Ketoreductases
Yuan, Bo
Page, Abigail
Worrall, Christopher P.
Escalettes, Franck
Willies, Simon C.
McDouall, Joseph J. W.
Turner, Nicholas J.
Clayden, Jonathan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (39) : 7010 - 7013
[19] Antiepileptic drug trials
Baulac, Michel
Cascino, Gregory D.
NEUROLOGY, 2015, 84 (20) : 2010 - 2011
[20] A Short Review on Synthetic Advances toward the Synthesis of Rufinamide, an Antiepileptic Drug
Padmaja, R. D.
Chanda, Kaushik
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2018, 22 (04) : 457 - 466

← 1 2 3 4 5 →