Bacterial siderophores: structure elucidation, and ill, 13C and 15N two-dimensional NMR assignments of azoverdin and related siderophores synthesized by Azomonas macrocytogenes ATCC 12334 - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue BioMetals Année : 1995

Bacterial siderophores: structure elucidation, and ill, 13C and 15N two-dimensional NMR assignments of azoverdin and related siderophores synthesized by Azomonas macrocytogenes ATCC 12334

Résumé

Two major azoverdins were isolated from the cultures of Azomonas macroo'togenes ATCC 12334 grown in iron-deficient medium. Their structures have been established using fast atom bombardment-mass spectroscopy, homonuclear and heteronuclear two-dimensional 15N, 13C and IH NMR, and circular dichroism techniques. These siderophores are chromopeptides possessing at the N-terminal end of their peptide chain the chromophore derived from 2,3-diamino-6,7-dihydroxyquinoline common to pyoverdins. The linear peptide chain (L)-Hse-(D)-AcOHOrn-(D)-Ser-(L)-AcOHOrn-(D)-Hse-(L)-CTHPMD has at its C-terminal end a new natural amino acid which is the result of the condensation of I mol of homoserine and 1 mol of 2,4-diaminobutyric acid forming a cyclic amidine belonging to the tetrahydropyrimidine family: 2-homoseryl-4-carboxyl-3,4,5,6-tetrahydropyrimidine. The azoverdins differ only by a substitutent bound to the nitrogen on C-3 of the chromophore: azoverdin, the most abundant one, possesses a succinamide moiety, whereas azoverdin A bears a succinic acid moiety, lSN-labelled azoverdin afforded readily, after the complete assignment of the ISN spectrum of the siderophore, a sequence determination of the peptidic part of the molecule and gave evidence for the presence of two tetrahydropyrimidine groups on the molecule: one on the chromophore and the second at the C-terminal end of the siderophore.

Dates et versions

hal-02359795 , version 1 (12-11-2019)

Identifiants

Citer

Jean Jacques Bernardini, Caroline Linget-Morice, François Hoh, Karen Collinson, Pavel Kyslik, et al.. Bacterial siderophores: structure elucidation, and ill, 13C and 15N two-dimensional NMR assignments of azoverdin and related siderophores synthesized by Azomonas macrocytogenes ATCC 12334. BioMetals, 1995, ⟨10.1007/BF00144615⟩. ⟨hal-02359795⟩
41 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More