In this paper, we report an efficient total synthesis of 5-deoxytoyocamycin, which was isolated from microbial sources with excellent antitumor activity. Our synthetic strategy uses 1,2,3-triacetate-5-deoxyribose as the starting material and Vorbrüggen glycosylation as the key step.
An enzyme substrate, 4-nitrophenyl-β-D-ribofuranoside, was synthesized from commercially available 1,2,3,5-tetra-O-acetyl-β-D-ribofuranoside and p-nitrophenol using an efficient glycosylation. The synthesized substrate can fulfill the requirements for the detection of ribofuranosidase.
A novel galactoside derivative (1) incorporating p-nitroaniline (p-NA) as chromophore has been synthesized and used as a cascaded chromogenic enzyme substrate for the detection of β-D-galactosidase, which was characterized using UV, 1H NMR, 13C NMR and MS spectra. A plausible mechanism for the release of p-NPA from the enzyme substrate 1 was proposed.
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