Total Syntheses of Fimsbactin A and B and Their Stereoisomers to Probe the Stereoselectivity of the Fimsbactin Uptake Machinery in Acinetobacter baumannii

Soojeung Kim; Haeun Lee; Woon Young Song; Hak Joong Kim

doi:10.1021/acs.orglett.0c00790

Total Syntheses of Fimsbactin A and B and Their Stereoisomers to Probe the Stereoselectivity of the Fimsbactin Uptake Machinery in Acinetobacter baumannii

Soojeung Kim, Haeun Lee, Woon Young Song, Hak Joong Kim

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

The stereoselective synthesis of fimsbactin A, a siderophore of the human pathogen Acinetobacter baumannii, was established. Based on this synthetic route, various fimsbactin stereoisomeric analogues were generated and tested for their iron delivery activity for A. baumannii. This investigation revealed that the fimsbactin uptake machinery in this bacterium was indeed highly stereoselective in substrate recognition.

Original language	English
Pages (from-to)	2806-2810
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.0c00790
Publication status	Published - 2020 Apr 3

Bibliographical note

Funding Information:
This work was supported by grants from Korea Centers for Disease Control and Prevention, Ministry of Health and Welfare, Republic of Korea (2019-ER5401-00), the National Research Foundation of Korea (NRF-2018R1D1A1A02086039), and the Korea Basic Science Institute (KBSI) National Research Facilities & Equipment Center (NFEC), funded by the Korea government (Ministry of Education) (2019R1A6C1010028). We also thank Prof. Hugh Kim for his helpful advice on this manuscript.

Publisher Copyright:
© 2020 American Chemical Society.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c00790

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title = "Total Syntheses of Fimsbactin A and B and Their Stereoisomers to Probe the Stereoselectivity of the Fimsbactin Uptake Machinery in Acinetobacter baumannii",

abstract = "The stereoselective synthesis of fimsbactin A, a siderophore of the human pathogen Acinetobacter baumannii, was established. Based on this synthetic route, various fimsbactin stereoisomeric analogues were generated and tested for their iron delivery activity for A. baumannii. This investigation revealed that the fimsbactin uptake machinery in this bacterium was indeed highly stereoselective in substrate recognition.",

author = "Soojeung Kim and Haeun Lee and Song, {Woon Young} and Kim, {Hak Joong}",

note = "Funding Information: This work was supported by grants from Korea Centers for Disease Control and Prevention, Ministry of Health and Welfare, Republic of Korea (2019-ER5401-00), the National Research Foundation of Korea (NRF-2018R1D1A1A02086039), and the Korea Basic Science Institute (KBSI) National Research Facilities & Equipment Center (NFEC), funded by the Korea government (Ministry of Education) (2019R1A6C1010028). We also thank Prof. Hugh Kim for his helpful advice on this manuscript. Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

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doi = "10.1021/acs.orglett.0c00790",

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AU - Lee, Haeun

AU - Song, Woon Young

AU - Kim, Hak Joong

N1 - Funding Information: This work was supported by grants from Korea Centers for Disease Control and Prevention, Ministry of Health and Welfare, Republic of Korea (2019-ER5401-00), the National Research Foundation of Korea (NRF-2018R1D1A1A02086039), and the Korea Basic Science Institute (KBSI) National Research Facilities & Equipment Center (NFEC), funded by the Korea government (Ministry of Education) (2019R1A6C1010028). We also thank Prof. Hugh Kim for his helpful advice on this manuscript. Publisher Copyright: © 2020 American Chemical Society.

PY - 2020/4/3

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N2 - The stereoselective synthesis of fimsbactin A, a siderophore of the human pathogen Acinetobacter baumannii, was established. Based on this synthetic route, various fimsbactin stereoisomeric analogues were generated and tested for their iron delivery activity for A. baumannii. This investigation revealed that the fimsbactin uptake machinery in this bacterium was indeed highly stereoselective in substrate recognition.

AB - The stereoselective synthesis of fimsbactin A, a siderophore of the human pathogen Acinetobacter baumannii, was established. Based on this synthetic route, various fimsbactin stereoisomeric analogues were generated and tested for their iron delivery activity for A. baumannii. This investigation revealed that the fimsbactin uptake machinery in this bacterium was indeed highly stereoselective in substrate recognition.

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Total Syntheses of Fimsbactin A and B and Their Stereoisomers to Probe the Stereoselectivity of the Fimsbactin Uptake Machinery in Acinetobacter baumannii

Abstract

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ASJC Scopus subject areas

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