Structure of azotobactin D, a siderophore of Azotobacter vinelandii strain D (CCM 289)

Biochemistry
1988.0

Abstract

The structure elucidation of azotobactin D, the fluorescent siderophore excreted by Azotobacter uinelandii strain D, has been accomplished by using essentially NMR techniques and FAB mass spectrometry. It is a chromopeptide possessing a chromophore derived from 2,3-diamino-6,7-dihydroxyquinoline bound to a peptide chain of 10 amino acids constituted with D- and L-serine (2), L-homoserine (3), D-citrulline (1), D-N'-acetyl-Nb-hydroxyornithine (1), L-aspartic acid (1), D-threo-P-hydroxyaspartic acid (1), and glycine (1). The chromophore is located at the N-terminus of the peptide, and one of the homoserines is at its C-terminus. The latter lactonizes readily, yielding a high amount of azotobactin 6, which is in fact the major compound isolated after the purification steps. The chromophore has an S chiral center. The structure of this siderophore differs significantly from the structure proposed by Fukasawa et al. [Fukasawa, K., Goto, M., Sasaki, K., Hirata, Y., & Sato, S. (1972) Tetrahedron 28, 5359-5365] for the fluorescent peptide excreted similarly by A. uinelandii strain 0.

Knowledge Graph

Similar Paper