Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid

Patrick Rabe; Tim A. Klapschinski; Nelson L. Brock; Christian A. Citron; Paul D'Alvise; Lone Gram; Jeroen S. Dickschat

doi:10.3762/bjoc.10.188

Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid

Patrick Rabe, Tim A. Klapschinski, Nelson L. Brock, Christian A. Citron, Paul D'Alvise, Lone Gram, Jeroen S. Dickschat

Rheinische Friedrich-Wilhelms-Universität Bonn

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Abstract

Tropodithietic acid (TDA) is a structurally unique sulfur-containing antibiotic from the Roseobacter clade bacterium Phaeobacter inhibens DSM 17395 and a few other related species. We have synthesised several structural analogues of TDA and used them in bioactivity tests against Staphylococcus aureus and Vibrio anguillarum for a structure-activity relationship (SAR) study, revealing that the sulfur-free analogue of TDA, tropone-2-carboxylic acid, has an antibiotic activity that is even stronger than the bioactivity of the natural product. The synthesis of this compound and of several analogues is presented and the bioactivity of the synthetic compounds is discussed.

Original language	English
Journal	Beilstein Journal of Organic Chemistry
Volume	10
Pages (from-to)	1796-1801
Number of pages	6
ISSN	2195-951X
DOIs	https://doi.org/10.3762/bjoc.10.188
Publication status	Published - 2014

Bibliographical note

This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)

Keywords

CHEMISTRY,
PHAEOBACTER-GALLAECIENSIS
NATURAL-PRODUCTS
BIOSYNTHESIS
ROSEOBACTER
THIOTROPOCIN
BACTERIA
INHIBENS
TROPONE
REVEAL
NOV.
antibiotics
natural products
Roseobacter
SAR study
tropodithietic acid
tropone

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3762/bjoc.10.188

Beilstein J Org Chem 10 1796 1 Final published version, 282 KB

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title = "Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid",

abstract = "Tropodithietic acid (TDA) is a structurally unique sulfur-containing antibiotic from the Roseobacter clade bacterium Phaeobacter inhibens DSM 17395 and a few other related species. We have synthesised several structural analogues of TDA and used them in bioactivity tests against Staphylococcus aureus and Vibrio anguillarum for a structure-activity relationship (SAR) study, revealing that the sulfur-free analogue of TDA, tropone-2-carboxylic acid, has an antibiotic activity that is even stronger than the bioactivity of the natural product. The synthesis of this compound and of several analogues is presented and the bioactivity of the synthetic compounds is discussed.",

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author = "Patrick Rabe and Klapschinski, {Tim A.} and Brock, {Nelson L.} and Citron, {Christian A.} and Paul D'Alvise and Lone Gram and Dickschat, {Jeroen S.}",

note = "This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)",

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T1 - Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid

AU - Rabe, Patrick

AU - Klapschinski, Tim A.

AU - Brock, Nelson L.

AU - Citron, Christian A.

AU - D'Alvise, Paul

AU - Gram, Lone

AU - Dickschat, Jeroen S.

N1 - This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)

PY - 2014

Y1 - 2014

N2 - Tropodithietic acid (TDA) is a structurally unique sulfur-containing antibiotic from the Roseobacter clade bacterium Phaeobacter inhibens DSM 17395 and a few other related species. We have synthesised several structural analogues of TDA and used them in bioactivity tests against Staphylococcus aureus and Vibrio anguillarum for a structure-activity relationship (SAR) study, revealing that the sulfur-free analogue of TDA, tropone-2-carboxylic acid, has an antibiotic activity that is even stronger than the bioactivity of the natural product. The synthesis of this compound and of several analogues is presented and the bioactivity of the synthetic compounds is discussed.

AB - Tropodithietic acid (TDA) is a structurally unique sulfur-containing antibiotic from the Roseobacter clade bacterium Phaeobacter inhibens DSM 17395 and a few other related species. We have synthesised several structural analogues of TDA and used them in bioactivity tests against Staphylococcus aureus and Vibrio anguillarum for a structure-activity relationship (SAR) study, revealing that the sulfur-free analogue of TDA, tropone-2-carboxylic acid, has an antibiotic activity that is even stronger than the bioactivity of the natural product. The synthesis of this compound and of several analogues is presented and the bioactivity of the synthetic compounds is discussed.

KW - CHEMISTRY,

KW - PHAEOBACTER-GALLAECIENSIS

KW - NATURAL-PRODUCTS

KW - BIOSYNTHESIS

KW - ROSEOBACTER

KW - THIOTROPOCIN

KW - BACTERIA

KW - INHIBENS

KW - TROPONE

KW - REVEAL

KW - NOV.

KW - antibiotics

KW - natural products

KW - Roseobacter

KW - SAR study

KW - tropodithietic acid

KW - tropone

U2 - 10.3762/bjoc.10.188

DO - 10.3762/bjoc.10.188

M3 - Journal article

C2 - 25161739

SN - 2195-951X

VL - 10

SP - 1796

EP - 1801

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid

Abstract

Bibliographical note

Keywords

UN SDGs

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