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The structure of syringomycins A 1 , E and G
Author(s) -
Segre A.,
Bachmann R.C.,
Ballio A.,
Bossa F.,
Grgurina I.,
Iacobellis N.S.,
Marino G.,
Pucci P.,
Simmaco M.,
Takemoto J.Y.
Publication year - 1989
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(89)81054-3
Subject(s) - chemistry
By a combination of 1D and 2D 1 H‐ and 13 C‐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 β‐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 A 1 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.