Carbohydrates, azido synthesis

Figure 17.12 Azido derivatives of sugars can be used as monomers for glycan and carbohydrate synthesis by cells. Such modifications can be probed using click chemistry or Staudinger ligation reactions.

M. Kiso, A. Yasm, and A. Hasegawa, Synthesis of 2-azido-2-deoxy-3,4 5,6-di-0-isopropyl-idene-aldehydo-D-aanoose dimethyl acetal and 4-azido-4-deoxy-2r3 5,6-di-0-isopropyI-i ene-aldehydo-D-piictoee dimethyl acetal, Carbohydr. Res. 127 137 (1984). 

G. Yang and F. Kong, Synthesis and glycosidic coupling reaction of substituted 2,6-dioxabicyclo[3.1.1]heptanes l,3-anhydro-2-azido-4,6-di-0-benzyl-2-deoxy-/ -D-manno-pyranose, Carbohydr. Res., 312 (1998) 77-83. 

M. Kloosterman, M. P. de Nijs, and J. H. van Boom, Synthesis of l,6-anhydro-2-0-trifluoromethanesulphonyl-/l-D-mannopyranose derivatives and their conversion into the corresponding l,6-anhydro-2-azido-2-deoxy-/ -D-glucopyranoses a convenient and efficient approach, J. Carbohydr. Chem., 5 (1986) 215-233 compare Ref. 129. 

Neu5Ac aldolase has also been used for the synthesis of 3-deoxy-D-mfl7j jo-octulosonic acid (KDO, 17) [16,17,20]. Condensation of o-arabinose (18) with pyruvate gave a mixture of KDO and 4-epi-KDO (19). Wong and coworkers have since reported the isolation of a KDO aldolase which produces KDO with complete stereospecificity at C-4 and also accepts a wide variety of carbohydrate substrates [51]. N-Acetylneuraminate synthase, found in Neisseria meningitidis, has been used to catalyse the condensation of 6-azido-6-deoxy-N-acetylmannosamine with phosphoenolpyruvate to give 9-azido-9-deoxy-Neu5Ac [52]. 

Bai, Y, Boons, G-J, Burton, A, Johnson, M, Haller, M, Vinyl glycosides in oligosaccharide synthesis (part 6) 3-buten-2-yl 2-azido-2-deoxy glycosides and 3-buten-2-yl 2-phthalimido-2-deoxy glycosides as novel glycosyl donors, J. Carbohydr. Chem., 19, 939-958, 2000. 

Bozo, E, Boros, S, Kuszmann, J, Synthesis of 4-cyanophenyl 2-azido-2-deoxy- and 3-azido-3-deoxy-1,5-dithio-p-D-xylopyranosides, Carbohydr. Res., 301, 23-32, 1997. 

Tber, B, Fahmi, N-E, Ronco, G, Villa, P, Ewing, D F, Mackenzie, G, An alternative strategy for the synthesis of 3 -azido-2, 3 -dideoxy-4 -thionucleosides starting from D-xylose, Carbohydr. Res., 267, 203-215, 1995. 

Broddefalk, J, Nilsson, U, Kihlberg, J, An improved synthesis of 3,4,6-tri-0-acetyl-2-azido-2-deoxy-a-D-galactopyranosyl bromide a key component for synthesis of glycopeptides and glycolipids, J. Carbohydr. Chem., 13, 129-132, 1994. 

---