Structure of acinetoferrin, a new citrate-based dihydroxamate siderophore from Acinetobacter haemolyticus.
From low-iron cultures of Acinetobacter haemolyticus ATCC 17906, a new hydroxamate siderophore was purified by XAD-7 adsorption followed by preparative thin layer chromatography. The siderophore, named acinetoferrin, released citric acid, 1,3-diaminopropane and (E)-2-octenoic acid upon hydrolysis with HCl, reductive hydrolysis with HI and oxidation with periodate, respectively. Structure elucidation by a combination of NMR spectroscopy and positive fast atom bombardment mass spectrometry revealed that acinetoferrin is a derivative of citric acid, both of its terminal carboxyl groups being symmetrically amide-linked with the 1-amino-3-(N-hydroxy-N-2-octenylamino)propane residues. The (E)-2-octenoic acid is novel as a component of the siderophores.
Okujo
N
N
Faculty of Pharmaceutical Sciences, Okayama University, Japan.
Sakakibara
Y
Y
Yoshida
T
T
Yamamoto
S
S
D000150:Acinetobacter / Q000737:chemistry* / Q000254:growth & development / Q000378:metabolism; D002951:Citrates / Q000032:analysis; D019343:Citric Acid; D003470:Culture Media; D006877:Hydroxamic Acids / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D007501:Iron / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D017262:Siderophores / Q000096:biosynthesis / Q000737:chemistry* / Q000302:isolation & purification; D016339:Spectrometry, Mass, Fast Atom Bombardment; D014233:Tricarboxylic Acids / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism
D002951:Citrates; D003470:Culture Media; D006877:Hydroxamic Acids; D017262:Siderophores; D014233:Tricarboxylic Acids; C086668:acinetoferrin; D019343:Citric Acid; D007501:Iron