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dc.contributor.authorOng, Li Linen_US
dc.contributor.authorWong, Kathy Pooi Wenen_US
dc.contributor.authorRaj, Surhabi Devaen_US
dc.contributor.authorKhong, Duc Thinhen_US
dc.contributor.authorPanda, Parthasarathien_US
dc.contributor.authorSantoso, Mardien_US
dc.contributor.authorJudeh, Zaher M. A.en_US
dc.identifier.citationOng, L. L., Wong, K. P. W., Raj, S. D., Khong, D. T., Panda, P., Santoso, M. & Judeh, Z. M. A. (2022). An orthogonal approach for the precise synthesis of phenylpropanoid sucrose esters. New Journal of Chemistry, 46(20), 9710-9717.
dc.description.abstractPhenylpropanoid sucrose esters (PSEs) are plant-derived metabolites that exist widely in medicinal plants and possess important bioactivities. Their precise synthesis is challenging due to the distinct and diverse substitution patterns at the sugar framework, and it is scarcely reported. Orthogonal protection/deprotection strategies for disaccharides are more complex and less developed than those for monosaccharides. We disclose a precise synthesis of PSEs starting from 2,1′:4,6-di-O-diisopropylidene sucrose 7via an orthogonal protection/deprotection and selective cinnamoylation strategy. We demonstrate the strategy for the synthesis of several PSEs cinnamoylated at the O-3 and O-4′ positions of diisopropylidene sucrose 7. The strategy is enabled by a carefully selected and synergistic set of protecting groups and deprotecting agents under the optimized conditions. It potentially gives access to the ∼150 reported PSEs and opens the door for the custom synthesis of unnatural PSEs for industrial applications. The reported work also presents a viable strategy for the general orthogonal protection/deprotection of disaccharides for the precise synthesis of other classes of phenylpropanoid esters and related compounds.en_US
dc.description.sponsorshipNanyang Technological Universityen_US
dc.relation.ispartofNew Journal of Chemistryen_US
dc.rights© 2022 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.en_US
dc.subjectEngineering::Chemical engineeringen_US
dc.titleAn orthogonal approach for the precise synthesis of phenylpropanoid sucrose estersen_US
dc.typeJournal Articleen
dc.contributor.schoolSchool of Chemical and Biomedical Engineeringen_US
dc.contributor.schoolInterdisciplinary Graduate School (IGS)en_US
dc.contributor.researchNTU Institute for Health Technologiesen_US
dc.description.versionPublished versionen_US
dc.subject.keywordsCustom Synthesisen_US
dc.description.acknowledgementWe thank the Interdisciplinary Graduate School and the School of Chemical and Biomedical Engineering, Nanyang Technological University, Singapore for financial support (CoE, Startup Grant).en_US
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