Preparation of site-specific isotopically labelled zervamicins, the antibiotic peptaibols produced by Emericellopsis salmosynnemata.
A simple procedure for the preparation of the specifically labelled peptide antibiotic zervamicins IC, IIA and IIB has been developed. The zervamicin molecules are labelled with stable isotopes by culturing the Emericellopsis salmosynnemata on a well-defined synthetic medium containing the highly isotopically enriched amino acid. To obtain the peptide with the specifically and highly enriched amino acid residue, precautions have been taken to prevent any de novo biosynthesis of the particular amino acid from unlabelled precursors. The enrichment of the labelled peptide is determined by mass spectrometric analysis. Following this method we have incorporated [2',4',5',6',7'-2H5]-L-Trp-1, [1'-15N]-L-Trp-1 and [2',3',4',5',6'-2H5]-L-Phl-16 into zervamicins IC, IIA and IIB on the preparative scale and without scrambling of the label. Thus, using the procedures described, isotopically labelled zervamicins can be prepared, allowing them to be studied by solid-state NMR.
Egorova-Zachernyuk
T A
TA
M. V. Lomonosov Moscow State Academy of Fine Chemical Technology, Russia.
Shvets
V I
VI
Versluis
K
K
Heerma
W
W
Creemers
A F
AF
Nieuwenhuis
S A
SA
Lugtenburg
J
J
Raap
J
J
D000900:Anti-Bacterial Agents / Q000096:biosynthesis / Q000302:isolation & purification / Q000378:metabolism*; D003903:Deuterium; D006999:Hypocreales / Q000378:metabolism*; D007473:Ion Channels; D007553:Isotope Labeling; D009587:Nitrogen Isotopes; D054848:Peptaibols; D010455:Peptides
D000900:Anti-Bacterial Agents; D007473:Ion Channels; D009587:Nitrogen Isotopes; D054848:Peptaibols; D010455:Peptides; C077076:zervamicin-IC; C077077:zervamicin IIB; C051145:zervamicin IIA; D003903:Deuterium