Development of a Microwave-assisted Chemoselective Synthesis of Oxime-linked Sugar Linkers and Trivalent Glycoclusters
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...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-03-01
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| Series: | Pharmaceuticals |
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| Online Access: | http://www.mdpi.com/1424-8247/12/1/39 |
| _version_ | 1828900418944499712 |
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| author | Katherine McReynolds Dustin Dimas Grace Floyd Kara Zeman |
| author_facet | Katherine McReynolds Dustin Dimas Grace Floyd Kara Zeman |
| author_sort | Katherine McReynolds |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-13T15:45:53Z |
| format | Article |
| id | doaj.art-492e82a6245145f48169eb443a95ae15 |
| institution | Directory Open Access Journal |
| issn | 1424-8247 |
| language | English |
| last_indexed | 2024-12-13T15:45:53Z |
| publishDate | 2019-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceuticals |
| spelling | doaj.art-492e82a6245145f48169eb443a95ae152022-12-21T23:39:41ZengMDPI AGPharmaceuticals1424-82472019-03-011213910.3390/ph12010039ph12010039Development of a Microwave-assisted Chemoselective Synthesis of Oxime-linked Sugar Linkers and Trivalent GlycoclustersKatherine McReynolds0Dustin Dimas1Grace Floyd2Kara Zeman3Department of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, CA 95819-6057, USADepartment of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, CA 95819-6057, USADepartment of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, CA 95819-6057, USADepartment of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, CA 95819-6057, USAA 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.http://www.mdpi.com/1424-8247/12/1/39Microwave reactionschemoselectiveoximeaminooxyglycoclustersmultivalent |
| spellingShingle | Katherine McReynolds Dustin Dimas Grace Floyd Kara Zeman Development of a Microwave-assisted Chemoselective Synthesis of Oxime-linked Sugar Linkers and Trivalent Glycoclusters Pharmaceuticals Microwave reactions chemoselective oxime aminooxy glycoclusters multivalent |
| title | Development of a Microwave-assisted Chemoselective Synthesis of Oxime-linked Sugar Linkers and Trivalent Glycoclusters |
| title_full | Development of a Microwave-assisted Chemoselective Synthesis of Oxime-linked Sugar Linkers and Trivalent Glycoclusters |
| title_fullStr | Development of a Microwave-assisted Chemoselective Synthesis of Oxime-linked Sugar Linkers and Trivalent Glycoclusters |
| title_full_unstemmed | Development of a Microwave-assisted Chemoselective Synthesis of Oxime-linked Sugar Linkers and Trivalent Glycoclusters |
| title_short | Development of a Microwave-assisted Chemoselective Synthesis of Oxime-linked Sugar Linkers and Trivalent Glycoclusters |
| title_sort | development of a microwave assisted chemoselective synthesis of oxime linked sugar linkers and trivalent glycoclusters |
| topic | Microwave reactions chemoselective oxime aminooxy glycoclusters multivalent |
| url | http://www.mdpi.com/1424-8247/12/1/39 |
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