2. Academic Validation
  3. Bioinspired Total Synthesis of Complex Nucleoside Antibiotics A201A, A201D and A201E

Bioinspired Total Synthesis of Complex Nucleoside Antibiotics A201A, A201D and A201E

  • Angew Chem Int Ed Engl. 2023 Jan 16;62(3):e202213810. doi: 10.1002/anie.202213810.
Jiaxiang Wang 1,  Jiahui Gao 1,  Tianyun Guo 1,  Xing Huo 1,  Wenhua Zhang 2,  Jian Liu 1,  Xiaolei Wang 1
Affiliations

Affiliations

  • 1 State Key Laboratory of Applied Organic Chemistry, Department of Chemistry and School of Pharmacy, Lanzhou University, Lanzhou, 730000, P. R. China.
  • 2 School of Life Sciences, Lanzhou University, Lanzhou, 730000, P. R. China.
PMID: 36411245 DOI: 10.1002/anie.202213810
Abstract

Herein, bioinspired total syntheses of A201A, A201D, and A201E based on a previously reported biosynthetic pathway are presented. The challenging 1,2-cis-furanoside, a core structure of the A201 family, was obtained by remote 2-quinolinecarbonyl-assisted glycosylation. We accomplished the total synthesis of A201A and A201E based on the critical 1,2-cis-furanoside moiety through late-stage glycosylation without any interference from basic dimethyl adenosine. We also confirmed the absolute configuration of A201E by total synthesis. This modular synthesis strategy enables efficient preparation of A201 family Antibiotics, allowing the study of their structure-activity relationships and mode of action. This study satisfies the increasing demand for developing novel Antibiotics inspired by the A201 family.

Keywords

Carbohydrates; Hydrogen-Bond-Assisted Glycosylation; Natural Products; Nucleoside Antibiotics; Total Synthesis.

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