Bacterial siderophores: structure elucidation, and 1H, 13C and 15N two-dimensional NMR assignments of azoverdin and related siderophores synthesized by Azomonas macrocytogenes ATCC 12334 |
| |
Authors: | Jean-Jacques Bernardini Caroline Linget-Morice François Hoh S. Karen Collinson Pavel Kyslík William J. Page Anne Dell Mohamed A. Abdallah |
| |
Affiliation: | (1) Laboratoire de Chimie Microbienne, URA 31 CNRS, Faculté de Chimie, Université Louis Pasteur, Strasbourg, France;(2) Department of Microbiology, University of Alberta, Edmonton, Canada;(3) Department of Microbiology, Czech Academy of Sciences, Prague, Czech Republic;(4) Department of Biochemistry, Imperial College, London, UK;(5) Laboratoire de Chimie Microbienne, URA 31 CNRS, Faculté de Chimie, Université Louis Pasteur, 1 rue Blaise Pascal, 67008 Strasbourg, France |
| |
Abstract: | Two major azoverdins were isolated from the cultures of Azomonas macrocytogenes ATCC 12334 grown in irondeficient medium. Their structures have been established using fast atom bombardment-mass spectroscopy, homonuclear and heteronuclear two-dimensional 15N, 13C and 1H 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 1 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. 15N-labelled azoverdin afforded readily, after the complete assignment of the 15N 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. |
| |
Keywords: | azoverdin Azomonas macrocytogenes 15N NMR siderophore iron transport |
本文献已被 SpringerLink 等数据库收录! |
|