Synthesis and antibacterial studies of teixobactin analogues with non-isostere substitution of enduracididine

Kang Jin; Kathy Hiu Laam Po; Wang Yeuk Kong; Chung Hei Lo; Chun Wah Lo; Ho Yin Lam; Amaya Sirinimal; Jonathan Avraham Reuven; Sheng Chen; Xuechen Li

doi:10.1016/j.bmc.2018.01.016

Synthesis and antibacterial studies of teixobactin analogues with non-isostere substitution of enduracididine

Kang Jin, Kathy Hiu Laam Po, Wang Yeuk Kong, Chung Hei Lo, Chun Wah Lo, Ho Yin Lam, Amaya Sirinimal, Jonathan Avraham Reuven, Sheng Chen, Xuechen Li

Research output: Journal article publication › Journal article › Academic research › peer-review

31 Citations (Scopus)

Abstract

Teixobactin is a structurally and mechanistically novel antimicrobial peptide with potent activities against Gram-positive pathogens. It contains L-allo-enduracididine (End) residue which is not readily accessible. In this report, we have used convergent Ser Ligation as the key step to prepare a series of teixobactin analogues with End being substituted with its non-isostere moieties. Among these analogues, compounds T16, T27 and T29 exhibited the best antimicrobial activities against different Gram-positive bacteria with MICs ranging from 0.25 to 1.0 µM. Structure-activity relationship is also established for further development of more promising teixobactin analogues.

Original language	English
Pages (from-to)	1062-1068
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	26
Issue number	5
DOIs	https://doi.org/10.1016/j.bmc.2018.01.016
Publication status	Published - 1 Mar 2018

Keywords

SAR study
Ser ligation
Teixobactin analogues

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

More information

10.1016/j.bmc.2018.01.016

Cite this

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abstract = "Teixobactin is a structurally and mechanistically novel antimicrobial peptide with potent activities against Gram-positive pathogens. It contains L-allo-enduracididine (End) residue which is not readily accessible. In this report, we have used convergent Ser Ligation as the key step to prepare a series of teixobactin analogues with End being substituted with its non-isostere moieties. Among these analogues, compounds T16, T27 and T29 exhibited the best antimicrobial activities against different Gram-positive bacteria with MICs ranging from 0.25 to 1.0 µM. Structure-activity relationship is also established for further development of more promising teixobactin analogues.",

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AU - Jin, Kang

AU - Po, Kathy Hiu Laam

AU - Kong, Wang Yeuk

AU - Lo, Chung Hei

AU - Lo, Chun Wah

AU - Lam, Ho Yin

AU - Sirinimal, Amaya

AU - Reuven, Jonathan Avraham

AU - Chen, Sheng

AU - Li, Xuechen

PY - 2018/3/1

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DO - 10.1016/j.bmc.2018.01.016

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Synthesis and antibacterial studies of teixobactin analogues with non-isostere substitution of enduracididine

Abstract

Keywords

ASJC Scopus subject areas

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