Novel bioactive lipodepsipeptides from Pseudomonas syringae: The pseudomycins

FEBS Letters

Di Giorgio, D.³  Pucci, P.⁴  Ferranti, P.⁴  Paci, M.¹  Ballio, A.³  Bossa, F.³  Segre, A.²  Scaloni, A.³  Strobel, G.A.⁵ 

[1] Dipartimento di Scienze e Tecnologie Chimiche, Università ‘Tor Vergata’, Roma, Italy;Istituto di Strutturistica Chimica ‘G. Giacomello’, CNR, Casella Postale 10, Montelibretti Stazione, Italy;Dipartimento di Scienze Biochimiche ‘A. Rossi Fanelli' e’ Centro di Biologia Molecolare del CNR, Università ‘La Sapienza’, P. le Aldo Moro 5, 00185 Roma, Italy;Servizio di Spettrometria di Massa CNR, e Dipartimento di Chimica Organica e Biologica, Università ‘Federico II’, Napoli, Italy;Department of Plant Pathology, Montana State University, Bozeman, MT 59717, USA

关键词: Phytotoxin;    Lipodepsipeptide;    Pseudomycin;    Syringomycin;    Pseudomonas syringae;    TFA;    trifluoroacetic acid;    FAB-MS;    fast atom bombardment mass spectrometry;    TBDMS;    t-butyldimethylsilyl;    Asp-(3OH);    3-hydroxyaspartic acid;    Thr(4-Cl);    4-chlorothreonine;    Dab;    2;    4-diaminobutyric acid;    Dhb;    dehydro-2-aminobutyric acid;    a Thr;    allothreonine;    2D NMR;    two-dimensional nuclear magnetic resonance;    NOE;    nuclear Overhauser effect;    TPPI;    time proportional phase increment;    FID;    free induction decay;    NOESY;    nuclear Overhauser effect correlated spectroscopy;    TOCSY;    total correlated spectroscopy;   

DOI  :  10.1016/0014-5793(94)01179-6

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

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.

【 授权许可】

Unknown