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. Author manuscript; available in PMC: 2012 Jan 21.
Published in final edited form as: ACS Chem Biol. 2010 Oct 22;6(1):95–100. doi: 10.1021/cb100267k

Figure 1.

Figure 1

Comparison of methods for glycodiversification of natural products. (a) In vitro glycorandomization. Reducing sugars are converted to sugar-1-phosphates by E1, a flexible anomeric kinase. E2, A suitably flexible sugar-1-phosphate nucleotidyltransferase activates each sugar phosphate to the corresponding nucleotide sugar. Large panels of NDP-donors are used to probe the specificity of natural product GTs. Grey oval represents diverse natural product or natural product-like aglycons (X = O, S, or NH). (b) In vivo glycodiversification via a ‘non-natural glycoside host’ strain. Reducing sugars and aglycons are fed to a bacterial host engineered to express E1, E2, and a promiscuous GT. The endogenous biosynthetic machinery ensures recycling of necessary cofactors and aglycons decorated with non-natural sugars are collected from the culture media. (c) In vivo glucoside host. Aglycons are fed into a bacterial host engineered to express a GT which uses endogenous dTDP/UDPGlc as the glycosyl donor.