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Enantioselective extraction of unprotected amino acids coupled with racemization

Title
Enantioselective extraction of unprotected amino acids coupled with racemization
Authors
Huang H.Jin Y.Shirbhate M.E.Kang D.Choi M.Chen Q.Kim Y.Kim S.-J.Byun I.-S.Wang M.Bouffard J.Kim S.K.Kim K.M.
Ewha Authors
김성진김영미김관묵Jean Bouffard
SCOPUS Author ID
김성진scopus; 김영미scopus; 김관묵scopus; Jean Bouffardscopus
Issue Date
2021
Journal Title
Nature Communications
ISSN
2041-1723JCR Link
Citation
Nature Communications vol. 12, no. 1
Publisher
Nature Research
Indexed
SCIE; SCOPUS WOS scopus
Document Type
Article
Abstract
Scalable and economical methods for the production of optically pure amino acids, both natural and unnatural, are essential for their use as synthetic building blocks. Currently, enzymatic dynamic kinetic resolution (DKR) underpins some of the most effective processes. Here we report the development of enantioselective extraction coupled with racemization (EECR) for the chirality conversion of underivatized amino acids. In this process, the catalytic racemization of amino acids in a basic aqueous solution is coupled with the selective extraction of one enantiomer into an organic layer. Back-extraction from the organic layer to an acidic aqueous solution then completes the deracemization of the amino acid. The automation of the EECR process in a recycling flow reactor is also demonstrated. Continuous EECR is made possible by the sterically hindered chiral ketone extractant 5, which prevents the coextraction of the copper racemization catalyst because of its nonplanar geometry. Furthermore, the extractant 5 unexpectedly forms imines with amino acids faster and with greater enantioselectivity than less bulky derivatives, even though 5 cannot participate in intramolecular resonance-assisted hydrogen bonding. These features may allow EECR to challenge the preponderance of enzymatic DKR in the production of enantiomerically enriched amino acids. © 2021, The Author(s).
DOI
10.1038/s41467-020-20402-x
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자연과학대학 > 화학·나노과학전공 > Journal papers
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