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.

Novel bioactive lipodepsipeptides from Pseudomonas syringae: the pseudomycins / Ballio, A; Bossa, F; Di Giorgio, D; Ferranti, Pasquale; Paci, M; Pucci, Pietro; Scaloni, A; Segre, A; Strobel, Ga. - In: FEBS LETTERS. - ISSN 0014-5793. - STAMPA. - 355:1(1994), pp. 96-100. [10.1016/0014-5793(94)01179-6]

Novel bioactive lipodepsipeptides from Pseudomonas syringae: the pseudomycins.

FERRANTI, PASQUALE;PUCCI, PIETRO;
1994

Abstract

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.
1994
Novel bioactive lipodepsipeptides from Pseudomonas syringae: the pseudomycins / Ballio, A; Bossa, F; Di Giorgio, D; Ferranti, Pasquale; Paci, M; Pucci, Pietro; Scaloni, A; Segre, A; Strobel, Ga. - In: FEBS LETTERS. - ISSN 0014-5793. - STAMPA. - 355:1(1994), pp. 96-100. [10.1016/0014-5793(94)01179-6]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/358609
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