Lipase-catalyzed enantioselective synthesis of (R,R)-lactide from alkyl lactate to produce PDLA (poly D-lactic acid) and stereocomplex PLA (poly lactic acid)
R-lactide, a pivotal monomer for the production of poly (D-lactic acid) (PDLA) or stereocomplex poly (lactic acid) (PLA) was synthesized from alkyl (R)-lactate through a lipase-catalyzed reaction without racemization. From among several types of lipase, only lipase B from Candida antarctica (Novozym...
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ftuisanist:oai:scholarworks.unist.ac.kr:201301/20351 2023-05-15T13:56:05+02:00 Lipase-catalyzed enantioselective synthesis of (R,R)-lactide from alkyl lactate to produce PDLA (poly D-lactic acid) and stereocomplex PLA (poly lactic acid) Jeon, Byoung Wook Lee, Jumin Kim, Hyun Sook Cho, Dae Haeng Lee, Hyuk Chang, Rakwoo Kim, Yong Hwan 2016-09-06 https://scholarworks.unist.ac.kr/handle/201301/20351 http://www.sciencedirect.com/science/article/pii/S0168165613002770 https://doi.org/10.1016/j.jbiotec.2013.06.021 ENG eng ELSEVIER SCIENCE BV JOURNAL OF BIOTECHNOLOGY, v.168, no.2, pp.201 - 207 0168-1656 http://www.sciencedirect.com/science/article/pii/S0168165613002770 https://scholarworks.unist.ac.kr/handle/201301/20351 3192 26747 2-s2.0-84885870929 000325978300011 doi:10.1016/j.jbiotec.2013.06.021 (R,R)-lactide Alkyl (R)-lactate Lipase Molecular sieve Novozym 435 ARTICLE ART 2016 ftuisanist https://doi.org/10.1016/j.jbiotec.2013.06.021 2022-05-15T05:27:34Z R-lactide, a pivotal monomer for the production of poly (D-lactic acid) (PDLA) or stereocomplex poly (lactic acid) (PLA) was synthesized from alkyl (R)-lactate through a lipase-catalyzed reaction without racemization. From among several types of lipase, only lipase B from Candida antarctica (Novozym 435; CAL-B) was effective in the reaction that synthesized (R,R)-lactide. Enantiopure (R,R)-lactide, which consisted of over 99% enantiomeric excess, was synthesized from methyl (R)-lactate through CAL-B catalysis. Removal of the methanol by-product was critical to obtain a high level of lactide conversion. The (R, R)lactide yield was 56% in a reaction containing 100 mg of Novozym 435, 10 mM methyl (R)-lactate and 1500 mg of molecular sieve 5 A in methyl tert-butyl ether (MTBE). The important monomer (R,R)-lactide that is required for the production of the widely recognized bio-plastic PDLA and the PLA stereocomplex can be obtained using this novel synthetic method. close Article in Journal/Newspaper Antarc* Antarctica ScholarWorks@UNIST (Ulsan National Institute of Science and Technology) Journal of Biotechnology 168 2 201 207 |
institution |
Open Polar |
collection |
ScholarWorks@UNIST (Ulsan National Institute of Science and Technology) |
op_collection_id |
ftuisanist |
language |
English |
topic |
(R,R)-lactide Alkyl (R)-lactate Lipase Molecular sieve Novozym 435 |
spellingShingle |
(R,R)-lactide Alkyl (R)-lactate Lipase Molecular sieve Novozym 435 Jeon, Byoung Wook Lee, Jumin Kim, Hyun Sook Cho, Dae Haeng Lee, Hyuk Chang, Rakwoo Kim, Yong Hwan Lipase-catalyzed enantioselective synthesis of (R,R)-lactide from alkyl lactate to produce PDLA (poly D-lactic acid) and stereocomplex PLA (poly lactic acid) |
topic_facet |
(R,R)-lactide Alkyl (R)-lactate Lipase Molecular sieve Novozym 435 |
description |
R-lactide, a pivotal monomer for the production of poly (D-lactic acid) (PDLA) or stereocomplex poly (lactic acid) (PLA) was synthesized from alkyl (R)-lactate through a lipase-catalyzed reaction without racemization. From among several types of lipase, only lipase B from Candida antarctica (Novozym 435; CAL-B) was effective in the reaction that synthesized (R,R)-lactide. Enantiopure (R,R)-lactide, which consisted of over 99% enantiomeric excess, was synthesized from methyl (R)-lactate through CAL-B catalysis. Removal of the methanol by-product was critical to obtain a high level of lactide conversion. The (R, R)lactide yield was 56% in a reaction containing 100 mg of Novozym 435, 10 mM methyl (R)-lactate and 1500 mg of molecular sieve 5 A in methyl tert-butyl ether (MTBE). The important monomer (R,R)-lactide that is required for the production of the widely recognized bio-plastic PDLA and the PLA stereocomplex can be obtained using this novel synthetic method. close |
format |
Article in Journal/Newspaper |
author |
Jeon, Byoung Wook Lee, Jumin Kim, Hyun Sook Cho, Dae Haeng Lee, Hyuk Chang, Rakwoo Kim, Yong Hwan |
author_facet |
Jeon, Byoung Wook Lee, Jumin Kim, Hyun Sook Cho, Dae Haeng Lee, Hyuk Chang, Rakwoo Kim, Yong Hwan |
author_sort |
Jeon, Byoung Wook |
title |
Lipase-catalyzed enantioselective synthesis of (R,R)-lactide from alkyl lactate to produce PDLA (poly D-lactic acid) and stereocomplex PLA (poly lactic acid) |
title_short |
Lipase-catalyzed enantioselective synthesis of (R,R)-lactide from alkyl lactate to produce PDLA (poly D-lactic acid) and stereocomplex PLA (poly lactic acid) |
title_full |
Lipase-catalyzed enantioselective synthesis of (R,R)-lactide from alkyl lactate to produce PDLA (poly D-lactic acid) and stereocomplex PLA (poly lactic acid) |
title_fullStr |
Lipase-catalyzed enantioselective synthesis of (R,R)-lactide from alkyl lactate to produce PDLA (poly D-lactic acid) and stereocomplex PLA (poly lactic acid) |
title_full_unstemmed |
Lipase-catalyzed enantioselective synthesis of (R,R)-lactide from alkyl lactate to produce PDLA (poly D-lactic acid) and stereocomplex PLA (poly lactic acid) |
title_sort |
lipase-catalyzed enantioselective synthesis of (r,r)-lactide from alkyl lactate to produce pdla (poly d-lactic acid) and stereocomplex pla (poly lactic acid) |
publisher |
ELSEVIER SCIENCE BV |
publishDate |
2016 |
url |
https://scholarworks.unist.ac.kr/handle/201301/20351 http://www.sciencedirect.com/science/article/pii/S0168165613002770 https://doi.org/10.1016/j.jbiotec.2013.06.021 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
JOURNAL OF BIOTECHNOLOGY, v.168, no.2, pp.201 - 207 0168-1656 http://www.sciencedirect.com/science/article/pii/S0168165613002770 https://scholarworks.unist.ac.kr/handle/201301/20351 3192 26747 2-s2.0-84885870929 000325978300011 doi:10.1016/j.jbiotec.2013.06.021 |
op_doi |
https://doi.org/10.1016/j.jbiotec.2013.06.021 |
container_title |
Journal of Biotechnology |
container_volume |
168 |
container_issue |
2 |
container_start_page |
201 |
op_container_end_page |
207 |
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1766263304623226880 |