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Pharmaceuticals 2019, 12(1), 39; https://doi.org/10.3390/ph12010039

Development of a Microwave-assisted Chemoselective Synthesis of Oxime-linked Sugar Linkers and Trivalent Glycoclusters

Department of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, CA 95819-6057, USA
*
Author to whom correspondence should be addressed.
Current address: Department of Chemistry and Biochemistry, The University of Oklahoma, 101 Stephenson Parkway, SLSRC, Room 1000, Norman, OK 73019-5251, USA.
Current address: Biocare Medical, 60 Berry Dr., Pacheco, CA 94553, USA.
Received: 19 February 2019 / Revised: 5 March 2019 / Accepted: 8 March 2019 / Published: 14 March 2019
(This article belongs to the Special Issue Carbohydrates 2018)
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Abstract

A rapid, high-yielding microwave-mediated synthetic procedure was developed and optimized using a model system of monovalent sugar linkers, with the ultimate goal of using this method for the synthesis of multivalent glycoclusters. The reaction occurs between the aldehyde/ketone on the sugars and an aminooxy moiety on the linker/trivalent core molecules used in this study, yielding acid-stable oxime linkages in the products and was carried out using equimolar quantities of reactants under mild aqueous conditions. Because the reaction is chemoselective, sugars can be incorporated without the use of protecting groups and the reactions can be completed in as little as 30 min in the microwave. As an added advantage, in the synthesis of the trivalent glycoclusters, the fully substituted trivalent molecules were the major products produced in excellent yields. These results illustrate the potential of this rapid oxime-forming microwave-mediated reaction in the synthesis of larger, more complex glycoconjugates and glycoclusters for use in a wide variety of biomedical applications. View Full-Text
Keywords: Microwave reactions; chemoselective; oxime; aminooxy; glycoclusters; multivalent Microwave reactions; chemoselective; oxime; aminooxy; glycoclusters; multivalent
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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McReynolds, K.; Dimas, D.; Floyd, G.; Zeman, K. Development of a Microwave-assisted Chemoselective Synthesis of Oxime-linked Sugar Linkers and Trivalent Glycoclusters. Pharmaceuticals 2019, 12, 39.

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