The structure of syringomycins A1, E and G.
By a combination of 1D and 2D 1H- and 13C-NMR, FAB-MS, and chemical and enzymatic reactions carried out at the milligram level, it has been demonstrated that syringomycin E, the major phytotoxic antibiotic produced by Pseudomonas syringae pv. syringae, is a new lipodepsipeptide. Its amino acid sequence is Ser-Ser-Dab-Dab-Arg-Phe-Dhb-4(Cl)Thr-3(OH)Asp with the beta-carboxy group of the C-terminal residue closing a macrocyclic ring on the OH group of the N-terminal Ser, which in turn is N-acylated by 3-hydroxydodecanoic acid. Syringomycins A1 and G, two other metabolites of the same bacterium, differ from syringomycin E only in their fatty acid moieties corresponding, respectively, to 3-hydroxydecanoic and 3-hydroxytetradecanoic acid.
Segre
A
A
Dipartimento di Scienze Biochimiche, Università La Sapienza, Roma, Italy.
Bachmann
R C
RC
Ballio
A
A
Bossa
F
F
Grgurina
I
I
Iacobellis
N S
NS
Marino
G
G
Pucci
P
P
Simmaco
M
M
Takemoto
J Y
JY
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000032:analysis; D000900:Anti-Bacterial Agents / Q000032:analysis* / Q000145:classification; D001426:Bacterial Proteins / Q000032:analysis* / Q000302:isolation & purification; D001427:Bacterial Toxins / Q000032:analysis*; D003652:Decanoic Acids / Q000032:analysis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010446:Peptide Fragments / Q000032:analysis; D010447:Peptide Hydrolases; D010456:Peptides, Cyclic / Q000032:analysis; D011549:Pseudomonas / Q000032:analysis / Q000378:metabolism*
D000596:Amino Acids; D000900:Anti-Bacterial Agents; D001426:Bacterial Proteins; D001427:Bacterial Toxins; D003652:Decanoic Acids; D010446:Peptide Fragments; D010456:Peptides, Cyclic; C032677:syringomycin; D010447:Peptide Hydrolases