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Please use this identifier to cite or link to this item: http://repository.iitr.ac.in/handle/123456789/8051
Title: Amalgamation of Synthetic Biology and Chemistry for High-Throughput Nonconventional Synthesis of the Antimalarial Drug Artemisinin
Authors: Singh D.
McPhee D.
Paddon C.J.
Cherry J.
Maurya G.
Mahale G.
Patel Y.
Kumar N.
Singh S.
Sharma B.
Kushwaha L.
Singh S.
Kumar A.
Published in: Organic Process Research and Development
Abstract: The development of a cost-effective process for the production of artemisinin, the precursor of all artemisinin-derived drugs, the first-line treatment for malaria, has been a long-pursued endeavor. The breakthrough achievement of coaxing genetically engineered yeast to express Artemisia annua genes for the commercial production of artemisinic acid, an advanced intermediate in the synthesis of artemisinin, has yet to fully realize an affordable malaria treatment for the poor because of the lack of a cost-effective chemical conversion into artemisinin. We describe herein a commercially feasible and pragmatic synthesis of artemisinin from amorpha-4,11-diene, an early-stage intermediate produced in 2-fold higher molar yield than engineered yeast cells can process into artemisinic acid. The key to this novel approach is an exceedingly effective functionalization of the isopropenyl group of amorphadiene via endo-epoxyamorphadiene to give dihydroartemisinic acid, which upon esterification followed by oxidation and cyclicization furnishes pure artemisinin in approximately 60% yield. © 2017 American Chemical Society.
Citation: Organic Process Research and Development (2017), 21(4): 551-558
URI: https://doi.org/10.1021/acs.oprd.6b00414
http://repository.iitr.ac.in/handle/123456789/8051
Issue Date: 2017
Publisher: American Chemical Society
Keywords: amorphadiene
Artemisia annua
artemisinic acid
artemisinin
endo epoxidation
malaria
ISSN: 10836160
Author Scopus IDs: 57198856967
26666174100
6602106652
7202723225
42761777200
24074519600
55523539100
55219988200
24784526700
26653833400
57194055804
57214305690
26663981200
Author Affiliations: Singh, D., Chemistry Research and Development, Ipca Laboratories Limited, Kandivali Industrial Estate, Kandivali West, Mumbai, 400067, India
McPhee, D., Research and Development, Amyris Inc., 5885 Hollis Street, Emeryville, CA 94608, United States
Paddon, C.J., Research and Development, Amyris Inc., 5885 Hollis Street, Emeryville, CA 94608, United States
Cherry, J., Research and Development, Amyris Inc., 5885 Hollis Street, Emeryville, CA 94608, United States
Maurya, G., Chemistry Research and Development, Ipca Laboratories Limited, Kandivali Industrial Estate, Kandivali West, Mumbai, 400067, India
Mahale, G., Chemistry Research and Development, Ipca Laboratories Limited, Kandivali Industrial Estate, Kandivali West, Mumbai, 400067, India
Patel, Y., Chemistry Research and Development, Ipca Laboratories Limited, Kandivali Industrial Estate, Kandivali West, Mumbai, 400067, India
Kumar, N., Chemistry Research and Development, Ipca Laboratories Limited, Kandivali Industrial Estate, Kandivali West, Mumbai, 400067, India
Singh, S., Chemistry Research and Development, Ipca Laboratories Limited, Kandivali Industrial Estate, Kandivali West, Mumbai, 400067, India
Sharma, B., Chemistry Research and Development, Ipca Laboratories Limited, Kandivali Industrial Estate, Kandivali West, Mumbai, 400067, India
Kushwaha, L., Chemistry Research and Development, Ipca Laboratories Limited, Kandivali Industrial Estate, Kandivali West, Mumbai, 400067, India
Singh, S., Chemistry Research and Development, Ipca Laboratories Limited, Kandivali Industrial Estate, Kandivali West, Mumbai, 400067, India
Kumar, A., Chemistry Research and Development, Ipca Laboratories Limited, Kandivali Industrial Estate, Kandivali West, Mumbai, 400067, India
Corresponding Author: Cherry, J.; Research and Development, Amyris Inc., 5885 Hollis Street, United States; email: cherry@amyris.com
Appears in Collections:Journal Publications [ECE]

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