The convergent total synthesis and antibacterial profile of the natural product streptothricin F.

Autor:	Dowgiallo MG; Department of Chemistry and Chemical Biology, Northeastern University Boston MA USA r.manetsch@northeastern.edu., Miller BC; Department of Chemistry and Chemical Biology, Northeastern University Boston MA USA r.manetsch@northeastern.edu., Kassu M; Department of Chemistry and Chemical Biology, Northeastern University Boston MA USA r.manetsch@northeastern.edu., Smith KP; Department of Pathology, Beth Israel Deaconess Medical Center Boston MA USA.; Harvard Medical School Boston MA USA., Fetigan AD; Department of Chemistry and Chemical Biology, Northeastern University Boston MA USA r.manetsch@northeastern.edu., Guo JJ; Department of Chemistry and Chemical Biology, Northeastern University Boston MA USA r.manetsch@northeastern.edu.; Center for Drug Discovery, Northeastern University Boston MA USA.; Barnett Institute for Chemical and Biological Analysis, Northeastern University Boston MA USA., Kirby JE; Department of Pathology, Beth Israel Deaconess Medical Center Boston MA USA.; Harvard Medical School Boston MA USA., Manetsch R; Department of Chemistry and Chemical Biology, Northeastern University Boston MA USA r.manetsch@northeastern.edu.; Department of Pharmaceutical Sciences, Northeastern University Boston MA USA.; Center for Drug Discovery, Northeastern University Boston MA USA.
Jazyk:	angličtina
Zdroj:	Chemical science [Chem Sci] 2022 Feb 25; Vol. 13 (12), pp. 3447-3453. Date of Electronic Publication: 2022 Feb 25 (Print Publication: 2022).
DOI:	10.1039/d1sc06445b
Abstrakt:	A convergent, diversity-enabling total synthesis of the natural product streptothricin F has been achieved. Herein, we describe the potent antimicrobial activity of streptothricin F and highlight the importance of a total synthesis that allows for the installation of practical divergent steps for medicinal chemistry exploits. Key features of our synthesis include a Burgess reagent-mediated 1,2- anti -diamine installation, diastereoselective azidation of a lactam enolate, and a mercury(ii) chloride-mediated desulfurization-guanidination. The development of this chemistry enables the synthesis and structure-activity studies of streptothricin F analogs. Competing Interests: The authors declare no competing financial interest. The HP D300 digital dispenser and TECAN M1000 used for MIC analysis in Table 1 were provided for our use by TECAN (Morrisville, NC). TECAN had no role in study design, data collection/interpretation, manuscript preparation, or decision to publish. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
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