Structure of vulnibactin, a new polyamine-containing siderophore from Vibrio vulnificus.
A new siderophore named vulnibactin has been isolated from low iron cultures of Vibrio vulnificus, a human pathogen. The structure was established as N-[3-(2,3-dihydroxybenzamido)propyl]-1,3-bis[2-(2-hydroxy-phenyl)- trans-5 - methyl-2-oxazoline-4-carboxamido]propane by a combination of acid hydrolysis, nuclear magnetic resonance spectroscopy and positive fast atom bombardment mass spectrometry. Vulnibactin is characterized as containing one residue of 2,3-dihydroxybenzoic acid as well as two residues of salicylic acid, both of which are involved in the formation of oxazoline rings with L-threonine bound to a norspermidine backbone. In addition, two other compounds with siderophore activity were purified and their structures were also determined. These two compounds provided further support for the structure of vulnibactin.
Okujo
N
N
Faculty of Pharmaceutical Sciences, Okayama University, Japan.
Saito
M
M
Yamamoto
S
S
Yoshida
T
T
Miyoshi
S
S
Shinoda
S
S
D000577:Amides / Q000737:chemistry* / Q000302:isolation & purification; D000818:Animals; D003470:Culture Media; D006868:Hydrolysis; D062385:Hydroxybenzoates / Q000032:analysis; D009682:Magnetic Resonance Spectroscopy; D010080:Oxazoles / Q000737:chemistry* / Q000302:isolation & purification; D012459:Salicylates / Q000032:analysis; D020156:Salicylic Acid; D017262:Siderophores / Q000737:chemistry* / Q000302:isolation & purification; D016339:Spectrometry, Mass, Fast Atom Bombardment; D014733:Vibrio / Q000737:chemistry*
D000577:Amides; D003470:Culture Media; D062385:Hydroxybenzoates; D010080:Oxazoles; D012459:Salicylates; D017262:Siderophores; C086667:vulnibactin; C009135:2,3-dihydroxybenzoic acid; D020156:Salicylic Acid