The structure of syringomycins A1, E and G

FEBS Letters

Pucci, P.¹  Grgurina, I.³  Marino, G.¹  Simmaco, M.³  Iacobellis, N.S.²  Bachmann, R.C.⁵  Ballio, A.³  Bossa, F.³  Segre, A.⁴  Takemoto, J.Y.⁵ 

[1] Dipartimento di Chimica Organica e Biologica, Università di Napoli, 80134 Napoli, Italy;Istituto Tossine e Micotossine da Parassiti Vegetali del CNR, 70126 Bari Italy;Dipartimento di Scienze Biochimiche e Centro di Biologia Molecolare del CNR, Università ‘La Sapienza’, 00185 Roma Italy;Istituto di Strutturistica Chimica ‘G. Giacomello’, CNR, Casella Postale 10, 00016 Monterotondo Stazione, Italy;Department of Biology, Utah State University, Logan, UT 84322-5305, USA

关键词: Phytotoxin;    Lipodepsipeptide;    Syringomycin A1;    Syringomycin E;    Syringomycin G;    Pseudomonas syringae pv. syringae;    DMSO;    dimethyl sulfoxide;    FAB-MS;    fast atom bombardment mass spectrometry;    Abu;    2-aminobutyric acid;    3(OH)Asp;    3-hydroxyaspartic acid;    Dab;    2;    4-diaminobutyric acid;    Dhb;    2;    3-dehydro-2-aminobutyric acid;    4(Cl)Thr;    4-chlorothreonine;    4(OH)Thr;    4-hydroxythreonine;    SR;    syringomycin;   

DOI  :  10.1016/0014-5793(89)81054-3

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

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 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 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.

【 授权许可】

Unknown