کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1389284 | 982859 | 2014 | 17 صفحه PDF | دانلود رایگان |

In this work, we describe the synthesis and NMR characterization of four mono- and four dideoxygenated analogs of α,α-d-trehalose. The symmetrical (2,2′-, 3,3′-, 4,4′- and 6,6′-) dideoxy analogs were obtained via selective protection and subsequent radical deoxygenation of the desired hydroxyl group set. The unsymmetrical (2′-, 3′-, 4′- and 6′-) monodeoxy analogs were synthesized by desymmetrization of α,α-trehalose and subsequent deoxygenation under radical conditions. Complete assignment of all 1H and 13C resonances in the spectra of these deoxytrehaloses was achieved through the extensive use of 2D {1H,1H} and {1H,13C} correlation NMR experiments. The synthesis of these trehalose analogs sets the stage for future biochemical and NMR-based studies to probe the substrate interactions of trehalose with the recently identified mycobacterial sulfotransferase Stf0.
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Journal: Carbohydrate Research - Volume 342, Issue 14, 15 October 2007, Pages 2014–2030