Synthesis of dehydroalanine fragments as thiostrepton side chain mimetics.
Syntheses of dehydroalanine derivatives via a solid-support route, starting from selenocystein, and via conventional solution phase chemistry are described along with initial biological testing. The target compounds were designed as mimetics of the dehydroalanine side chain of the macrocyclic antibiotic thiostrepton that acts on the bacterial ribosome.
Ayida
Benjamin K
BK
Department of Medicinal Chemistry, Anadys Pharmaceuticals, Inc., 3115 Merryfield Row, San Diego, CA 92121, USA.
Simonsen
Klaus B
KB
Vourloumis
Dionisios
D
Hermann
Thomas
T
D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002853:Chromatography, Liquid; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D018716:Molecular Mimicry; D013883:Thiostrepton / Q000737:chemistry* / Q000494:pharmacology
C015102:dehydroalanine; D013883:Thiostrepton; D000409:Alanine