Reference : Synthesis and biological evaluation of potential threonine synthase inhibitors: Rhizo...
Scientific journals : Article
Physical, chemical, mathematical & earth Sciences : Chemistry
Life sciences : Microbiology
http://hdl.handle.net/2268/155608
Synthesis and biological evaluation of potential threonine synthase inhibitors: Rhizocticin A and Plumbemycin A.
English
Gahungu, Mathias mailto [Université de Liège - ULiège > Centre de recherches du cyclotron > > >]
Arguelles Arias, Anthony mailto [Université de Liège - ULiège > > Centre d'ingénierie des protéines >]
Fickers, Patrick mailto [Université Libre de Bruxelles - ULB > Biotechnologies et Bioprocedes >]
Zervosen, Astrid mailto [Université de Liège - ULiège > > Centre de recherches du cyclotron >]
Joris, Bernard mailto [Université de Liège - ULiège > Département des sciences de la vie > Physiologie et génétique bactériennes >]
Damblon, Christian mailto [Université de Liège - ULiège > Département de chimie (sciences) > Chimie biologique structurale >]
Luxen, André mailto [Université de Liège - ULiège > Département de chimie (sciences) > Chimie organique de synthèse >]
2013
Bioorganic & Medicinal Chemistry
Elsevier Science
21
17
4958-67
Yes (verified by ORBi)
International
0968-0896
1464-3391
Oxford
United Kingdom
[en] (S,Z)-APPA ; Phosphonate antibiotic ; Plumbemycin ; Rhizocticin ; Threonine synthase inhibitors
[en] Rhizocticins and Plumbemycins are natural phosphonate antibiotics produced by the bacterial strains Bacillus subtilis ATCC 6633 and Streptomyces plumbeus, respectively. Up to now, these potential threonine synthase inhibitors have only been synthesized under enzymatic catalysis. Here we report the chemical stereoselective synthesis of the non-proteinogenic (S,Z)-2-amino-5-phosphonopent-3-enoic acid [(S,Z)-APPA] and its use for the synthesis of Rhizocticin A and Plumbemycin A. In this work, (S,Z)-APPA was synthesized via the Still-Gennari olefination starting from Garner's aldehyde. The Michaelis-Arbuzov reaction was used to form the phosphorus-carbon bond. Oligopeptides were prepared using liquid phase peptide synthesis (LPPS) and were tested against selected bacteria and fungi.
Centre de Recherches du Cyclotron - CRC ; Centre d'Ingénierie des Protéines - CIP
Researchers ; Professionals
http://hdl.handle.net/2268/155608
also: http://hdl.handle.net/2268/171954
10.1016/j.bmc.2013.06.064
Copyright (c) 2013 Elsevier Ltd. All rights reserved.

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