Lipase-mediated regioselective modifications of macrolactonic sophorolipids
Abstract Chemoenzymatic synthesis and modification of well-defined macrolactonic sophorolipid (SLML) analogues via a series of successive regioselective de-esterification/transesterification reactions is investigated. Of the lipases screened, Candida antartica lipase- B (Novozyme-435) successfully d...
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ftnazarbayevuniv:oai:testnur.nu.edu.kz:123456789/2952 2023-05-15T14:15:35+02:00 Lipase-mediated regioselective modifications of macrolactonic sophorolipids Aliya, Sembayeva Sembayeva, Aliya Berhane, Beniam Carr, Jason A. 2017-04-06 http://nur.nu.edu.kz/handle/123456789/2952 https://doi.org/10.1016/j.tet.2017.02.043 https://www.sciencedirect.com/science/article/pii/S0040402017301825 en eng Tetrahedron Tetrahedron © 2017 Elsevier Ltd. All rights reserved. Sophorolipids Glycolipids Lipases NMR spectroscopy Lactone Fatty acid esters Biosurfactant Article 2017 ftnazarbayevuniv https://doi.org/10.1016/j.tet.2017.02.043 2019-04-02T14:35:55Z Abstract Chemoenzymatic synthesis and modification of well-defined macrolactonic sophorolipid (SLML) analogues via a series of successive regioselective de-esterification/transesterification reactions is investigated. Of the lipases screened, Candida antartica lipase- B (Novozyme-435) successfully deacylated the C-6′ acetoxy group of natural and peracylated SLMLs. Subsequent transesterification with acylating agents (esters of fatty acids) was successful only with the C-6′ deacetylated natural SLML providing an avenue to well-defined analogues of varying amphilicity. The macrolactonic motif was essential for enzymatic recognition of the sophorose rings of these complex glycolipids. In the absence of the lactonic motif, the peracylated sophorose rings are not deacylated, rather the carboxyl end of the non-lactonic forms that was preferentially transesterified. All macrolactonic derivatives were characterized by IR, 1H, 13C, 1H-1H and 1H-13C NMR spectroscopy, as well as HRMS where applicable. Article in Journal/Newspaper antartic* Nazarbayev University Repository Tetrahedron 73 14 1873 1880 |
institution |
Open Polar |
collection |
Nazarbayev University Repository |
op_collection_id |
ftnazarbayevuniv |
language |
English |
topic |
Sophorolipids Glycolipids Lipases NMR spectroscopy Lactone Fatty acid esters Biosurfactant |
spellingShingle |
Sophorolipids Glycolipids Lipases NMR spectroscopy Lactone Fatty acid esters Biosurfactant Aliya, Sembayeva Sembayeva, Aliya Berhane, Beniam Carr, Jason A. Lipase-mediated regioselective modifications of macrolactonic sophorolipids |
topic_facet |
Sophorolipids Glycolipids Lipases NMR spectroscopy Lactone Fatty acid esters Biosurfactant |
description |
Abstract Chemoenzymatic synthesis and modification of well-defined macrolactonic sophorolipid (SLML) analogues via a series of successive regioselective de-esterification/transesterification reactions is investigated. Of the lipases screened, Candida antartica lipase- B (Novozyme-435) successfully deacylated the C-6′ acetoxy group of natural and peracylated SLMLs. Subsequent transesterification with acylating agents (esters of fatty acids) was successful only with the C-6′ deacetylated natural SLML providing an avenue to well-defined analogues of varying amphilicity. The macrolactonic motif was essential for enzymatic recognition of the sophorose rings of these complex glycolipids. In the absence of the lactonic motif, the peracylated sophorose rings are not deacylated, rather the carboxyl end of the non-lactonic forms that was preferentially transesterified. All macrolactonic derivatives were characterized by IR, 1H, 13C, 1H-1H and 1H-13C NMR spectroscopy, as well as HRMS where applicable. |
format |
Article in Journal/Newspaper |
author |
Aliya, Sembayeva Sembayeva, Aliya Berhane, Beniam Carr, Jason A. |
author_facet |
Aliya, Sembayeva Sembayeva, Aliya Berhane, Beniam Carr, Jason A. |
author_sort |
Aliya, Sembayeva |
title |
Lipase-mediated regioselective modifications of macrolactonic sophorolipids |
title_short |
Lipase-mediated regioselective modifications of macrolactonic sophorolipids |
title_full |
Lipase-mediated regioselective modifications of macrolactonic sophorolipids |
title_fullStr |
Lipase-mediated regioselective modifications of macrolactonic sophorolipids |
title_full_unstemmed |
Lipase-mediated regioselective modifications of macrolactonic sophorolipids |
title_sort |
lipase-mediated regioselective modifications of macrolactonic sophorolipids |
publisher |
Tetrahedron |
publishDate |
2017 |
url |
http://nur.nu.edu.kz/handle/123456789/2952 https://doi.org/10.1016/j.tet.2017.02.043 https://www.sciencedirect.com/science/article/pii/S0040402017301825 |
genre |
antartic* |
genre_facet |
antartic* |
op_relation |
Tetrahedron |
op_rights |
© 2017 Elsevier Ltd. All rights reserved. |
op_doi |
https://doi.org/10.1016/j.tet.2017.02.043 |
container_title |
Tetrahedron |
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73 |
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14 |
container_start_page |
1873 |
op_container_end_page |
1880 |
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1766287933790224384 |