Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays
Diglycose derivatives, consisting of two monosaccharides linked at non-anomeric positions by a bridging nitrogen atom, have been synthesised. Conversion of one of the precursor monosaccharide coupling components into an unsaturated derivative enhances its electrophilicity at the allylic position, fa...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2011-08-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.7.128 |
| _version_ | 1819062895909011456 |
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| author | Ian Cumpstey Jens Frigell Elias Pershagen Tashfeen Akhtar Elena Moreno-Clavijo Inmaculada Robina Dominic S. Alonzi Terry D. Butters |
| author_facet | Ian Cumpstey Jens Frigell Elias Pershagen Tashfeen Akhtar Elena Moreno-Clavijo Inmaculada Robina Dominic S. Alonzi Terry D. Butters |
| author_sort | Ian Cumpstey |
| collection | DOAJ |
| description | Diglycose derivatives, consisting of two monosaccharides linked at non-anomeric positions by a bridging nitrogen atom, have been synthesised. Conversion of one of the precursor monosaccharide coupling components into an unsaturated derivative enhances its electrophilicity at the allylic position, facilitating coupling reactions. Mitsunobu coupling between nosylamides and 2,3-unsaturated-4-alcohols gave the 4-amino-pseudodisaccharides with inversion of configuration as single regio- and diastereoisomers. A palladium-catalysed coupling between an amine and a 2,3-unsaturated 4-trichloroacetimidate gave a 2-amino-pseudodisaccharide as the major product, along with other minor products. Derivatisation of the C=C double bond in pseudodisaccharides allowed the formation of Man(N4–6)Glc and Man(N4–6)Man diglycosides. The amine-linked diglycosides were found to show weak glycosidase inhibitory activity. |
| first_indexed | 2024-12-21T15:06:03Z |
| format | Article |
| id | doaj.art-aa6d4c41b8c3436095de710c4f8b67e2 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-21T15:06:03Z |
| publishDate | 2011-08-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-aa6d4c41b8c3436095de710c4f8b67e22022-12-21T18:59:27ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972011-08-01711115112310.3762/bjoc.7.1281860-5397-7-128Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assaysIan Cumpstey0Jens Frigell1Elias Pershagen2Tashfeen Akhtar3Elena Moreno-Clavijo4Inmaculada Robina5Dominic S. Alonzi6Terry D. Butters7Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, SwedenDepartment of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, SwedenDepartment of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, SwedenDepartment of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, SwedenDepartment of Organic Chemistry, Faculty of Chemistry, University of Seville, Prof. García González, 1, 41012 Seville, SpainDepartment of Organic Chemistry, Faculty of Chemistry, University of Seville, Prof. García González, 1, 41012 Seville, SpainGlycobiology Institute, Department of Biochemistry, Oxford University, South Parks Road, Oxford, OX1 3QU, EnglandGlycobiology Institute, Department of Biochemistry, Oxford University, South Parks Road, Oxford, OX1 3QU, EnglandDiglycose derivatives, consisting of two monosaccharides linked at non-anomeric positions by a bridging nitrogen atom, have been synthesised. Conversion of one of the precursor monosaccharide coupling components into an unsaturated derivative enhances its electrophilicity at the allylic position, facilitating coupling reactions. Mitsunobu coupling between nosylamides and 2,3-unsaturated-4-alcohols gave the 4-amino-pseudodisaccharides with inversion of configuration as single regio- and diastereoisomers. A palladium-catalysed coupling between an amine and a 2,3-unsaturated 4-trichloroacetimidate gave a 2-amino-pseudodisaccharide as the major product, along with other minor products. Derivatisation of the C=C double bond in pseudodisaccharides allowed the formation of Man(N4–6)Glc and Man(N4–6)Man diglycosides. The amine-linked diglycosides were found to show weak glycosidase inhibitory activity.https://doi.org/10.3762/bjoc.7.128aminationglycomimeticsglycosidasesMitsunobupseudodisaccharides |
| spellingShingle | Ian Cumpstey Jens Frigell Elias Pershagen Tashfeen Akhtar Elena Moreno-Clavijo Inmaculada Robina Dominic S. Alonzi Terry D. Butters Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays Beilstein Journal of Organic Chemistry amination glycomimetics glycosidases Mitsunobu pseudodisaccharides |
| title | Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays |
| title_full | Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays |
| title_fullStr | Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays |
| title_full_unstemmed | Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays |
| title_short | Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays |
| title_sort | amine linked diglycosides synthesis facilitated by the enhanced reactivity of allylic electrophiles and glycosidase inhibition assays |
| topic | amination glycomimetics glycosidases Mitsunobu pseudodisaccharides |
| url | https://doi.org/10.3762/bjoc.7.128 |
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