[Chemical synthesis of 15N-labeled zervamicins IIB].
Analogues of 16-membered peptide antibiotic zervamicin IIB with the Gln3 and Gln11 residues 15N-labeled at the C alpha-atoms were synthesized by coupling the antibiotic segments (1-4), (5-9), and (10-16). In turn, these were prepared by a stepwise chain elongation in solution starting from their C-termini using benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) as an activating agent. The sterically hindered 2-aminoisobutyric acid was introduced by the BOP-dimethylaminopyridine system with the preactivation of the carboxyl component. The segment condensation was performed with the use of the 6-trifluoromethylbenzotriazol-1-yloxy-tris(pyrrolidino)phosphonium hexafluorophosphate activating reagent. The homogeneity of the resulting zervamicin analogues was confirmed by HPLC, and their structures were proved by NMR spectroscopy and FAB mass spectrometry.
Rimawi
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Lomonosov State Academy of Fine Chemical Technology, pr. Vernadskogo 86, Moscow, 117571 Russia. biotechnology@mtu-net.ru
Ogrel
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Raap
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Shvets
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D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D005998:Glycine / Q000737:chemistry; D007553:Isotope Labeling; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009584:Nitrogen / Q000737:chemistry*; D054848:Peptaibols; D010455:Peptides
D000900:Anti-Bacterial Agents; D054848:Peptaibols; D010455:Peptides; C077077:zervamicin IIB; D009584:Nitrogen; D005998:Glycine