𝔖 Bobbio Scriptorium
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Asymmetric synthesis of the hydroxylamino sugar of calicheamicin

✍ Scribed by William R. Roush; Bruce C. Follows

Book ID
104214506
Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
409 KB
Volume
35
Category
Article
ISSN
0040-4039

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✦ Synopsis

A ste~hemically general procedure for the conversion of 2,3epoxyalcohols to N-alkoxy oxazolidinones via the DBU promoted cyclizations of 2,3cpoxy-N-alkoxyun~haneurethanes has been developed and applied to the first asymmetric synthesis of the calicheamicin hyclroxylamino sugar, 7. Aryl tetrasacchakle 1 has been identified as the major DNA binding and mcognition substructure of calicheamicin, a potent double strand DNA-cleaving enediyne antibiotic that binds and cleaves DNA fmm within the minor gmove. *2 Oligosaccharide 1 contains several novel structural elements that presumably connibute to the DNA portion-bong properties,~~dej including the 2,4,~~~oxy-~~o sugar (B residue) and the hydroxylamino linkage connecting the A and B x&dues. In anticipation that conjugates of aryl tetrasaccharide 1 @

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