Structure of syringotoxin, a bioactive metabolite of Pseudomonas syringae pv. syringae

FEBS Letters

Gallo, M.²  Pucci, P.²  Simmaco, M.⁶  Paci, M.⁴  Iacobellis, N.S.³  Ballio, A.⁶  Bossa, F.¹  Segre, A.⁵  Collina, A.⁵  Scaloni, A.⁶ 

[1] Servizio di Spettrometria di Massa CNR, Università Federico II, 80134 Napoli, Italy;Istituto Tossine e Micotossine da Parassiti Vegetali del CNR, 70126 BariItaly;Dipartimento di Scienze e Tecnologie Chimiche, Università 'Tor Vergata', 00173 Roma, Italy;Istituto di Strutturistica Chimica ‘G. Giacomello’, CNR, Casella Postale 10,00016 Montelibretti Stazione, Italy;Dipartimento di Scienze Biochimiche e Centra di Biologia Molecolare del CNR, Università ‘La Sapienzars, 00185 RomaItaly

关键词: Phytotoxin;    Lipodepsipeptide;    Syringotoxin;    Pseudomonas syringae pv. syringae;    DMSO;    dimethyl sulf oxide;    FAB-MS;    fast atom bombardment mass spectrometry;    TBDMS;    t-butyldimethylsilyl;    (3-OH)Asp;    3-hydroxyaspartic acid;    Dab;    2;    4-diaminobutyric acid;    Dhb;    2;    3-dehydro-2-aminobutyric acid;    (4-Cl)Thr;    4-chlorothreonine;    Hse;    homoserine;    Hse>;    homoserine lactone;    (4-OH)Thr;    4-hydroxythreonine;    aThr;    allo-threonine;    DQF-COSY;    double quantum filtered correlated spectroscopy;    TOCSY;    total correlated spectroscopy;    NOESY;    nuclear Overhauser effect correlated spectroscopy;    SR;    syringomyein;    ST;    syringotoxin;   

DOI  :  10.1016/0014-5793(90)81197-V

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

The covalent structure of syringotoxin, a bioactive metabolite of Pseudomonas syringae pv. syringae isolates, pathogenic on various species of citrus trees, has been deduced from ID and 2D ¹H- and ¹³C-NMR spectra combined with extensive FAB-MS data and results of some chemical reactions. Similarly to syringomicins and syringostatins, produced by other plant pathogenic strains of P. syringae pv. syringae, syringotoxin is a lipodep-sinonapeptide. Its peptide moiety corresponds to Ser-Dab-Gly-Hse-Om-aThr-Dhb-(3-OH)Asp-(4-Cl)Thr with the terminal carboxy group closing a macrocyclic ring on the OH group of the N-terminal Ser, which in turn is N-acetylated by 3-hydroxytetradecanoic acid.

【 授权许可】

Unknown