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...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Journal article |
| Language: | English |
| Published: |
2011
|
| _version_ | 1797102140963946496 |
|---|---|
| author | Cumpstey, I Frigell, J Pershagen, E Akhtar, T Moreno-Clavijo, E Robina, I Alonzi, D Butters, T |
| author_facet | Cumpstey, I Frigell, J Pershagen, E Akhtar, T Moreno-Clavijo, E Robina, I Alonzi, D Butters, T |
| author_sort | Cumpstey, I |
| collection | OXFORD |
| 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 | 2024-03-07T06:01:42Z |
| format | Journal article |
| id | oxford-uuid:ec6a4db1-f3da-4448-a4b6-61ea0aaef835 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T06:01:42Z |
| publishDate | 2011 |
| record_format | dspace |
| spelling | oxford-uuid:ec6a4db1-f3da-4448-a4b6-61ea0aaef8352022-03-27T11:17:18ZAmine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:ec6a4db1-f3da-4448-a4b6-61ea0aaef835EnglishSymplectic Elements at Oxford2011Cumpstey, IFrigell, JPershagen, EAkhtar, TMoreno-Clavijo, ERobina, IAlonzi, DButters, TDiglycose 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. |
| spellingShingle | Cumpstey, I Frigell, J Pershagen, E Akhtar, T Moreno-Clavijo, E Robina, I Alonzi, D Butters, T Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays. |
| 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 |
| work_keys_str_mv | AT cumpsteyi aminelinkeddiglycosidessynthesisfacilitatedbytheenhancedreactivityofallylicelectrophilesandglycosidaseinhibitionassays AT frigellj aminelinkeddiglycosidessynthesisfacilitatedbytheenhancedreactivityofallylicelectrophilesandglycosidaseinhibitionassays AT pershagene aminelinkeddiglycosidessynthesisfacilitatedbytheenhancedreactivityofallylicelectrophilesandglycosidaseinhibitionassays AT akhtart aminelinkeddiglycosidessynthesisfacilitatedbytheenhancedreactivityofallylicelectrophilesandglycosidaseinhibitionassays AT morenoclavijoe aminelinkeddiglycosidessynthesisfacilitatedbytheenhancedreactivityofallylicelectrophilesandglycosidaseinhibitionassays AT robinai aminelinkeddiglycosidessynthesisfacilitatedbytheenhancedreactivityofallylicelectrophilesandglycosidaseinhibitionassays AT alonzid aminelinkeddiglycosidessynthesisfacilitatedbytheenhancedreactivityofallylicelectrophilesandglycosidaseinhibitionassays AT butterst aminelinkeddiglycosidessynthesisfacilitatedbytheenhancedreactivityofallylicelectrophilesandglycosidaseinhibitionassays |