Synthesis of mono- and dideoxygenated alpha,alpha-trehalose analogs.
In this work, we describe the synthesis and NMR characterization of four mono- and four dideoxygenated analogs of alpha,alpha-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 alpha,alpha-trehalose and subsequent deoxygenation under radical conditions. Complete assignment of all (1)H and (13)C resonances in the spectra of these deoxytrehaloses was achieved through the extensive use of 2D [(1)H,(1)H] and [(1)H,(13)C] 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.
Lin
Fiona L
FL
Department of Chemistry, University of California, Berkeley, CA 94720, USA.
van Halbeek
Herman
H
Bertozzi
Carolyn R
CR
D002236:Carbohydrate Conformation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D014199:Trehalose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D014199:Trehalose