204918-56-9Relevant articles and documents
Characterization of a distinct arabinofuranosyltransferase in Mycobacterium smegmatis
Zhang, Jian,Khoo, Kay-Hooi,Wu, Sz-Wei,Chatterjee, Delphi
, p. 9650 - 9662 (2007)
The D-arabinans in Mycobacterium are essential, extraordinarily complex entity comprised of D-arabinofuranose residues which are rarely found in nature. Despite the well-recognized importance of the mycobacterial arabinan, delineation of the arabinosylati
Neighboring-group participation by C-2 ether functions in glycosylations directed by nitrile solvents
Chao, Chin-Sheng,Lin, Ching-Yu,Mulani, Shaheen,Hung, Wei-Cheng,Mong, Kwok-Kong Tony
, p. 12193 - 12202 (2011/12/01)
Ether-protecting functions at C-2 hydroxy groups have been found to play participating roles in glycosylations when the reactions are conducted in nitrile solvent mixtures. The participation mechanism is based on intramolecular interaction between the lone electron pair of the oxygen atom of the C-2 ether function and the nitrile molecule when they are positioned in a cis configuration. A 1,2-cis glycosyl oxazolinium intermediate is formed. This participation, in conjunction with the anomeric effect of the glycosyl donor, confers high 1,2-trans selectivities on glycosylations. Further application of this concept has led to efficient preparations of α-(1→5)-arabinan oligomers.
Arabinofuranosyl oligosaccharides from mycobacteria: Synthesis and effect of glycosylation on ring conformation and hydroxymethyl group rotamer populations
D'Souza, Francis W.,Ayers, Joseph D.,McCarren, Patrick R.,Lowary, Todd L.
, p. 1251 - 1260 (2007/10/03)
A series of αD-arabinofuranosyl oligosaccharides (2-8) that are fragments of the arabinan portions of two polysaccharides present in the cell wall of Mycobacterium tuberculosis have been synthesized. Preparation of the oligosaccharides involved the sequen