Glycosyl phosphate analogues

Figure 6.51 Production of a non-fissile glycosyl phosphate analogue via the Michaelis-Arbusov reaction.

Isosteric analogues of glycosyl phosphates phosphorothioates, boranophosphates, phosphoroamidates... 

The replacement of the anomeric oxygen with a phosphor atom has been reported for the generation of non-isosteric analogues of glycosyl phosphates (Fig. 30).59 This class of compounds however has not found applications. 

T. Kannan, S. Vinodhkumar, B. Varghese, and D. Loganathan, Synthesis of glycosyl phos-phoramidate Novel isosteric analogues of glycosyl phosphates, Bioorq. Med. Chem. Lett., 11... 

The Lipid A analogues (84) - (88) have been synthesized. The 4,6-disulphated 1-thyminyl-analogue (85) had anti-HIV activity, while the analogues (86) and (87), in which the natural a-glycosyl phosphate moiety is substituted by a phosphono-oigrethyl group, had anti-tumour activity. ... 

A number of deoxy-, dideo y-monofluoro-, and dideoxy-difluoro-o-D-glucopyranosyl phosphates have been prepared for a comparative study of their acid hydrolysis rates. As in the hydrolysis of alkyl glycosides, deoxy derivatives reacted faster and fluorinated analogues much slower than the parent 1-phosphates, and it was concluded that the transition states for the hydrolysis of glycosides and glycosyl phosphates are essentially identical. ... 

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