Volume 52, Issue 35 pp. 9082-9084

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Elimination Reactions of Esters in the Biosynthesis of Polyketides and Ribosomal Peptides^†

Dr. Bartlomiej Krawczyk,

Dr. Bartlomiej Krawczyk

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 124, 10623 Berlin (Germany)

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Eric F. van Herwerden,

Eric F. van Herwerden

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 124, 10623 Berlin (Germany)

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Prof. Dr. Herman S. Overkleeft,

Prof. Dr. Herman S. Overkleeft

Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2300 RA Leiden (The Netherlands)

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Prof. Dr. Roderich D. Süssmuth,

Corresponding Author

Prof. Dr. Roderich D. Süssmuth

[email protected]

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 124, 10623 Berlin (Germany)

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 124, 10623 Berlin (Germany)Search for more papers by this author

Dr. Bartlomiej Krawczyk,

Dr. Bartlomiej Krawczyk

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 124, 10623 Berlin (Germany)

Search for more papers by this author

Eric F. van Herwerden,

Eric F. van Herwerden

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 124, 10623 Berlin (Germany)

Search for more papers by this author

Prof. Dr. Herman S. Overkleeft,

Prof. Dr. Herman S. Overkleeft

Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2300 RA Leiden (The Netherlands)

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Prof. Dr. Roderich D. Süssmuth,

Corresponding Author

Prof. Dr. Roderich D. Süssmuth

[email protected]

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 124, 10623 Berlin (Germany)

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 124, 10623 Berlin (Germany)Search for more papers by this author

First published: 09 August 2013

https://doi.org/10.1002/anie.201304851

Citations: 2

^†

H.S.O. acknowledges the Alexander von Humboldt Foundation for a Friedrich Wilhelm Bessel Research Award. This work was supported by the cluster of excellence UniCat (granted by the German research council-DFG).

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Graphical Abstract

Enoyl intermediates are normally obtained through β-elimination of β-hydroxy carbonyl compounds. The OH group is eliminated either directly or is first activated through phosphorylation. Alternative strategies have now been identified: Glutamination or acetylation of a β-hydroxycarbonyl compound followed by β-elimination of an ester was proven to be a key step in the biosynthesis of class I lantipeptide and tetronate antibiotics.

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Volume52, Issue35

August 26, 2013

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Elimination Reactions of Esters in the Biosynthesis of Polyketides and Ribosomal Peptides^†

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Elimination Reactions of Esters in the Biosynthesis of Polyketides and Ribosomal Peptides^†