Related Experiment Video
Updated: Jul 12, 2025
From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes Tü6028
Published on: January 13, 2017
Total Synthesis of Nikkomycin Sz and Nikkomycin Soz
Shuai Fan1, Tai Jiang1, Muhammad Nasir Siddique1
1State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
Abstract:
The nikkomycins Sz/Soz are a class of locked nucleoside antibiotics that share a common [5,6] trans-bicyclic core. Herein we present an efficient synthesis of these nikkomycins from diene, using neighboring group participation N-glycosylation and stereoselective oxidation state installation. This synthetic strategy overcomes several challenges due to the poor redox tolerance of the uracil base, the high strain of the trans-fused furanopyran C8 monosaccharides, and the acid-sensitive glycosidic bond when dealing with the deoxynucleotide natural product nikkomycin Sz.
