Precursor-Directed Syntheses and Biological Evaluation of New Elansolid Derivatives

Heinrich Steinmetz; Wiebke Zander; Muftah A.M. Shushni; Rolf Jansen; Klaus Gerth; Richard Dehn; Gerald Dräger; Andreas Kirschning; Rolf Müller

doi:10.1002/cbic.201200228

Precursor-Directed Syntheses and Biological Evaluation of New Elansolid Derivatives

Heinrich Steinmetz
, Wiebke Zander
, Muftah A.M. Shushni
, Rolf Jansen
, Klaus Gerth
, Richard Dehn
, Gerald Dräger
, Andreas Kirschning
, Rolf Müller^*

^*Corresponding author for this work

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

Abstract

The antibiotic elansolid C1 (8) was isolated from Chitinophaga sancti strain FxGBF13 after fermentation in the presence of anthranilic acid. Remarkably, 8 was also obtained by addition of anthranilic acid to a crude fermentation extract containing the macrolide elansolid A2 (1*). This Michael-type conjugate addition allowed us to generate 21 new derivatives of elansolid C1 (9-29) by using various nucleophiles. Biological activities of all derivatives were evaluated against Staphylococcus aureus, Micrococcus luteus, and the mouse cell line L929.

Original language	English
Pages (from-to)	1813-1817
Number of pages	5
Journal	ChemBioChem
Volume	13
Issue number	12
DOIs	https://doi.org/10.1002/cbic.201200228
Publication status	Published - 17 Jul 2012

Keywords

Anthranilic acid
Antibiotics
Elansolid
Liquid chromatography
Nucleophiles

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Organic Chemistry

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10.1002/cbic.201200228

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abstract = "The antibiotic elansolid C1 (8) was isolated from Chitinophaga sancti strain FxGBF13 after fermentation in the presence of anthranilic acid. Remarkably, 8 was also obtained by addition of anthranilic acid to a crude fermentation extract containing the macrolide elansolid A2 (1*). This Michael-type conjugate addition allowed us to generate 21 new derivatives of elansolid C1 (9-29) by using various nucleophiles. Biological activities of all derivatives were evaluated against Staphylococcus aureus, Micrococcus luteus, and the mouse cell line L929.",

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author = "Heinrich Steinmetz and Wiebke Zander and Shushni, \{Muftah A.M.\} and Rolf Jansen and Klaus Gerth and Richard Dehn and Gerald Dr{\"a}ger and Andreas Kirschning and Rolf M{\"u}ller",

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doi = "10.1002/cbic.201200228",

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AU - Steinmetz, Heinrich

AU - Zander, Wiebke

AU - Shushni, Muftah A.M.

AU - Jansen, Rolf

AU - Gerth, Klaus

AU - Dehn, Richard

AU - Dräger, Gerald

AU - Kirschning, Andreas

AU - Müller, Rolf

PY - 2012/7/17

Y1 - 2012/7/17

N2 - The antibiotic elansolid C1 (8) was isolated from Chitinophaga sancti strain FxGBF13 after fermentation in the presence of anthranilic acid. Remarkably, 8 was also obtained by addition of anthranilic acid to a crude fermentation extract containing the macrolide elansolid A2 (1*). This Michael-type conjugate addition allowed us to generate 21 new derivatives of elansolid C1 (9-29) by using various nucleophiles. Biological activities of all derivatives were evaluated against Staphylococcus aureus, Micrococcus luteus, and the mouse cell line L929.

AB - The antibiotic elansolid C1 (8) was isolated from Chitinophaga sancti strain FxGBF13 after fermentation in the presence of anthranilic acid. Remarkably, 8 was also obtained by addition of anthranilic acid to a crude fermentation extract containing the macrolide elansolid A2 (1*). This Michael-type conjugate addition allowed us to generate 21 new derivatives of elansolid C1 (9-29) by using various nucleophiles. Biological activities of all derivatives were evaluated against Staphylococcus aureus, Micrococcus luteus, and the mouse cell line L929.

KW - Anthranilic acid

KW - Antibiotics

KW - Elansolid

KW - Liquid chromatography

KW - Nucleophiles

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AN - SCOPUS:84864776550

SN - 1439-4227

VL - 13

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EP - 1817

JO - ChemBioChem

JF - ChemBioChem

IS - 12

ER -

Precursor-Directed Syntheses and Biological Evaluation of New Elansolid Derivatives

Abstract

Keywords

ASJC Scopus subject areas

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