Article Dans Une Revue Chemistry - A European Journal Année : 2017

Total synthesis and biological assessment of novel albicidins discovered by mass spectrometric networking

Résumé

Natural products represent an important source of potential novel antimicrobial drug leads. Low production by microorganisms in cell culture often delays the structural elucidation or even prevents a timely discovery. Starting from the anti-Gram-negative antibacterial compound albicidin produced by Xanthomonas albilineans, we describe a bioactivity-guided approach combined with non-targeted tandem mass spectrometry and spectral (molecular) networking for the discovery of novel antimicrobial compounds. We report eight new natural albicidin derivatives, four of which bear a β-methoxy cyanoalanine or β-methoxy asparagine as the central α-amino acid. We present the total synthesis of these albicidins, which facilitated the unambiguous determination of the (2S,3R)-stereoconfiguration which is complemented by the assessment of the stereochemistry on antibacterial activity.

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hal-01608574 , version 1 (26-05-2020)

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Leonard von Eckardstein, Daniel Petras, Tam Dang, Stéphane Cociancich, Souhir Sabri, et al.. Total synthesis and biological assessment of novel albicidins discovered by mass spectrometric networking. Chemistry - A European Journal, 2017, 23 (61), pp.1-6. ⟨10.1002/chem.201704074⟩. ⟨hal-01608574⟩
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