Novel bioactive lipodepsipeptides from Pseudomonas syringae: the pseudomycins.
The covalent structure and most of the stereochemistry of the pseudomycins, bioactive metabolites of a transposon-generated mutant of a Pseudomonas syringae wild-type strain proposed for the biological control of Dutch elm disease, have been determined. While two pseudomycins are identical to the known syringopeptins 25-A and 25-B, pseudomycins A, B, C, C' are new lipodepsinonapeptides. For all of these the peptide moiety corresponds to L-Ser-D-Dab-L-Asp-L-Lys-L-Dab-L-aThr-Z-Dhb-L-Asp(3-OH) -L-Thr (4-Cl) with the terminal carboxyl group closing a macrocyclic ring on the OH group of the N-terminal Ser. This is in turn N-acylated by 3,4-dihydroxytetradecanoate in pseudomycin A, by 3-hydroxytetradecanoate in pseudomycin B, by 3,4-dihydroxyhexadecanoate in pseudomycin C, and by 3-hydroxyhexadecanoate in pseudomycin C'. Some preliminary data on the biological activity of pseudomycin A are reported.
Dipartimento di Scienze Biochimiche A. Rossi Fanelli, Università La Sapienza, Roma, Italy.
A
A
Ballio
F
F
Bossa
D
D
Di Giorgio
P
P
Ferranti
M
M
Paci
P
P
Pucci
A
A
Scaloni
A
A
Segre
G A
GA
Strobel
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000032:analysis; D000935:Antifungal Agents / Q000737:chemistry* / Q000494:pharmacology; D001426:Bacterial Proteins / Q000737:chemistry* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D005227:Fatty Acids / Q000032:analysis; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D010455:Peptides / Q000737:chemistry* / Q000494:pharmacology; D010944:Plants / Q000187:drug effects / Q000378:metabolism; D011549:Pseudomonas / Q000737:chemistry*
D000596:Amino Acids; D000935:Antifungal Agents; D001426:Bacterial Proteins; D005227:Fatty Acids; D010455:Peptides