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

[21] Biocatalytic Asymmetric Synthesis of Chiral Aryl Alcohols
Bai, Dongya
He, Junyao
Ouyang, Bin
Huang, Jin
Wang, Pu
PROGRESS IN CHEMISTRY, 2017, 29 (05) : 491 - 501
[22] Biocatalytic combinatorial synthesis
Krstenansky, JL
Khmelnitsky, Y
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (10) : 2157 - 2162
[23] Process Development of C-N Cross-Coupling and Enantioselective Biocatalytic Reactions for the Asymmetric Synthesis of Niraparib
Chung, Cheol K.
Bulger, Paul G.
Kosjek, Birgit
Belyk, Kevin M.
Rivera, Nelo
Scott, Mark E.
Humphrey, Guy R.
Limanto, John
Bachert, Donald C.
Emerson, Khateeta M.
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2014, 18 (01) : 215 - 227
[24] Biocatalytic Strategy for Highly Diastereo- and Enantioselective Synthesis of 2,3-Dihydrobenzofuran-Based Tricyclic Scaffolds
Vargas, David A.
Khade, Rahul L.
Zhang, Yong
Fasan, Rudi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (30) : 10148 - 10152
[25] Bioequivalence of Intravenous and Oral Formulations of the Antiepileptic Drug Lacosamide
Cawello, Willi
Bonn, Rainer
Boekens, Hilmar
PHARMACOLOGY, 2012, 90 (1-2) : 40 - 46
[26] Chiral pool approach for the synthesis of functionalized amino acids: synthesis of antiepileptic drug (R)-lacosamide
Aratikatla, Eswar K.
Bhattacharya, Asish K.
TETRAHEDRON LETTERS, 2015, 56 (42) : 5802 - 5803
[27] Effectiveness of first antiepileptic drug
Kwan, P
Brodie, MJ
EPILEPSIA, 2001, 42 (10) : 1255 - 1260
[28] Topiramate: A new antiepileptic drug
Markind, JE
AMERICAN JOURNAL OF HEALTH-SYSTEM PHARMACY, 1998, 55 (06) : 554 - 562
[29] Zonisamide: A new antiepileptic drug
Sobieszek, G
Borowicz, KK
Kimber-Trojnar, Z
Malek, R
Piskorska, B
Czuczwar, SJ
POLISH JOURNAL OF PHARMACOLOGY, 2003, 55 (05): : 683 - 689
[30] Antiepileptic Drug Therapy and Monitoring
Podell, Michael
TOPICS IN COMPANION ANIMAL MEDICINE, 2013, 28 (02) : 59 - 66

← 1 2 3 4 5 →