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Organic letters
02 16, 2018;20 (4): 1126-1129.

Diverted Total Synthesis of the Baulamycins and Analogues Reveals an Alternate Mechanism of Action.

Andrew D Steele, Guillaume Ernouf, Young Eun Lee, William M Wuest
Author Information
  1. Andrew D Steele: Department of Chemistry, Emory University , 1515 Dickey Drive Atlanta, Georgia 30322, United States.
  2. Guillaume Ernouf: Department of Chemistry, Emory University , 1515 Dickey Drive Atlanta, Georgia 30322, United States.
  3. Young Eun Lee: Department of Chemistry, Temple University , 1901 North 13th Street Philadelphia, Pennsylvania 19122, United States.
  4. William M Wuest: Department of Chemistry, Emory University , 1515 Dickey Drive Atlanta, Georgia 30322, United States. ORCID
PMID: 29388431 DOI: 10.1021/acs.orglett.8b00054

Abstract

The baulamycins were identified as in vitro siderophore biosynthesis inhibitors. Diverted total synthesis was used to construct the natural products and eight strategic analogues, three of which had improved inhibitory activity. Biological testing then revealed that membrane damage is the predominant mode of action in Staphylococcus aureus cells.

References

  1. J Am Chem Soc. 2014 Jan 29;136(4):1579-86 [PMID: 24401083]
  2. Chem Rev. 2017 Oct 11;117(19):12415-12474 [PMID: 28953368]
  3. J Am Chem Soc. 2017 May 31;139(21):7188-7191 [PMID: 28502178]
  4. J Org Chem. 2006 Oct 27;71(22):8329-51 [PMID: 17064003]
  5. Biochemistry. 2017 Nov 28;56(47):6177-6178 [PMID: 29125284]
  6. Clin Microbiol Rev. 1993 Apr;6(2):137-49 [PMID: 8472246]
  7. J Am Chem Soc. 2015 Jun 17;137(23):7314-7 [PMID: 26024439]
  8. J Am Chem Soc. 2004 Feb 4;126(4):1038-40 [PMID: 14746469]
  9. Chembiochem. 2014 Oct 13;15(15):2211-5 [PMID: 25147134]
  10. Microbiol Mol Biol Rev. 2007 Sep;71(3):413-51 [PMID: 17804665]
  11. Appl Environ Microbiol. 1997 Jun;63(6):2421-31 [PMID: 9172364]
  12. J Am Chem Soc. 2016 May 11;138(18):5833-6 [PMID: 27096543]
  13. J Org Chem. 2017 Mar 3;82(5):2414-2435 [PMID: 28194974]
  14. J Org Chem. 2017 Dec 15;82(24):12947-12966 [PMID: 28903000]
  15. Nature. 2017 Jul 26;547(7664):436-440 [PMID: 28748934]
  16. J Med Chem. 2008 Sep 11;51(17):5349-70 [PMID: 18690677]
  17. Arch Med Res. 2005 Nov-Dec;36(6):697-705 [PMID: 16216651]
  18. J Org Chem. 2015 Jul 17;80(14):7076-88 [PMID: 26108800]

Grants

  1. R35 GM119426/NIGMS NIH HHS

MeSH Term

Anti-Bacterial Agents
Biological Products
Fatty Alcohols
Molecular Structure
Resorcinols
Staphylococcus aureus

Chemicals

Anti-Bacterial Agents
Biological Products
Fatty Alcohols
Resorcinols
Journal Article Research Support, Non-U.S. Gov't
Article has an altmetric score of 6

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