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Biodegradation of 1,2,3-Trichloropropane to Valuable (S)-2,3-DCP Using a One-Pot Reaction System

Bogale, Tadesse Fantaye; Gul, Ijaz; Wang, Le; Deng, Jiao; Chen, Yong; Majerić Elenkov, Maja; Tang, Lixia (2020) Biodegradation of 1,2,3-Trichloropropane to Valuable (S)-2,3-DCP Using a One-Pot Reaction System. Catalysts, 10 (1). ISSN 2073-4344

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Abstract

1, 2, 3-trichloropropane (TCP) being one of the important environmental pollutants, has drawn significant concern due to its highly toxic and carcinogenic effects. In this study, we built a one-pot reaction system in which immobilized haloalkane dehalogenase (DhaA31) and halohydrin dehalognase (HheC) were used to catalyze the recalcitrant TCP to produce 2, 3-dichloro-1-propanol (2, 3-DCP) by removing epichlorohydrin (ECH). SinceHheCdisplays a highRenantiopreference toward 2, 3-DCP, the production of enantiopure (S)-2, 3-DCP was expected. However, the enantioselective resolution of (R, S)-2, 3-DCP by HheC was greatly inhibited by the circular reaction occurring between the product ECH and 1, 3-dichloro-2-propanol (1.3-DCP). To resolve this problem, HZD-9 resin-based in situ product removal was implemented. Under the optimized conditions, TCP was completely consumed, resulting in optically pure (S)-2, 3-DCP with enantiomer excess (e.e) > 99% and 40% yield (out of the 44% theoretical maximum). The scale-up resin-integrated reaction system was successfully carried out in 0.5 L batch reactor. Moreover, the system could be reused for 6 rounds with 64% of original activity retained, showing that it could be applied in the treatment of large volumes of liquid waste and producing enantiopure (S)-2, 3-DCP.

Item Type: Article
Uncontrolled Keywords: immobilized dehalogenases ; 1, 2, 3-trichloropropane ; enantiopure compound ; one-pot reaction ; in-situ product removal
Subjects: BIOTECHNICAL SCIENCES > Biotechnology
Divisions: Division of Organic Chemistry and Biochemistry
Depositing User: Maja Majerić Elenkov
Date Deposited: 07 Dec 2020 10:25
Last Modified: 07 Dec 2020 10:25
URI: http://fulir.irb.hr/id/eprint/6080
DOI: 10.3390/catal10010003

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