Abstract
This paper describes the chemical characterization of staphyloferrin B, a new complexone type siderophore isolated from low iron cultures of Staphylococcus hyicus DSM 20459. Purification of the very hydrophilic metabolite was achieved by anion exchange high performance liquid chromatography HPLC. Mass spectrometry showed a molecular mass of 448 amu. Hydrolysis with 8 mHCl revealed the presence of l-2,3-diaminopropionic acid, citrate, ethylenediamine and succinic semialdehyde. The connections between the four building blocks were determined by two-dimensional nuclear magnetic resonance measurements. UV/Vis and circular dichroism spectra are consistent with the proposed structure, which could also be confirmed by precursor feeding. The siderophore activity of staphyloferrin B was demonstrated by iron transport measurements.
Similar content being viewed by others
References
Arnow LE. 1937 Colorimetric determination of the components of 3,4-dihydroxy-phenylalanine-tyrosine mixtures. J Biol Chem 118, 531–537.
Cooper AJL, Redfield AG. 1975 Proton magnetic resonance studies of α-keto acids. J Biol Chem 250, 527–532.
Cove JH, Holland KT, Cunliff WJ. 1980 The vitamin requirements of staphylococci isolated from the human skin. J Appl Bacteriol 49, 29–37.
Csaky TZ. 1948 On the estimation of bound hydroxylamine in biological materials. Acta Chem Scand 2, 450–454.
Drechsel H, Metzger J, Freund S, Jung G, Boelaert J, Winkelmann G. 1991 Rhizoferrin—a novel siderophore from the fungus Rhizopus microsporus var. rhizopodiformis. Biol Met 4, 238–243.
Drechsel H, Jung G, Winkelmann G. 1992 Stereochemical characterization of rhizoferrin and identification of its dehydration products. Bio Metals 5, 141–148.
Frank H, Woiwode W, Nicholson G, Bayer E. 1981 Determination of the rate of acidic catalyzed racemization of protein amino acids. Liebigs Annal Chem 1981 354–365.
Haag H, Fiedler P, Meiwes J, Zähner H, Dreschel H, Jung G. 1993 Fermentation and isolation of staphyloferrin B, a compound with siderophore activity from staphylococci. FEMS Microbiol Lett, submitted.
Kalinowski H-O, Berger S, Braun S. 1984 13C-NMR-Spektroskopie. Stuttgart: G. Thieme Verlag.
Kalnitsky G. 1953 The non-enzymatic oxidation of α-ketoglutarate. J Biol Chem 201, 817–823.
Konetschny-Rapp S, Jung G, Meiwes J, Zähner H. 1990 Staphyloferrin A: a structurally new siderophore from staphylococci. Eur J Biochem 191, 65–74.
Meiwes J, Fiedler HP, Haag H, Zähner H, Konetschny-Rapp S, Jung G. 1990 Isolation and characterization of staphyloferrin A, a compound with siderophore activity from Staphylococcus hyicus DSM 20459. FEMS Microbiol Lett 67, 201–206.
Neilands JB. 1991 A brief history of iron metabolism. Biol Met 4, 1–6.
Rackis JJ, Kalnitsky G. 1957 The non-enzymatic oxidation of α-ketoglutarate. II. The products of the reaction. J Biol Chem 225, 751–758.
Rioux C, Jordan DC, Rattray JBM. 1983 Colorimetric determination of catechol siderophores in microbial cultures. Anal Biochem 133, 163–169.
Schwyn B, Neilands JB. 1987 Universal chemical assay for the detection and determination of siderophores. Anal Biochem 160, 47–56.
Smith MJ, Shoolery JN, Schwyn B, Holden I, Neilands JB. 1985 Rhizobactin, a structurally novel siderophore from Rhizobiurn meliloti. J Am Chem Soc 107, 1739–1743.
Thieken A, Winkelmann G. 1992 Rhizoferrin: a complexone type siderophore of the Mucorales and Entomophthorales (Zygomycetes). FEMS Microbiol Lett 94, 37–42.
Winkelmann G. 1991 Handbook of Microbial Iron Chelates. Boca Raton, FL: CRC Press.
Yamamoto S, Fujiata Y, Okujo N, Minami C, Matsuura S, Shinoda S. 1992 Isolation and paritial characterization of a compound with siderophore activity from Vibrio parahaemolyticus. FEMS Microbiol Lett 94, 181–186.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Drechsel, H., Freund, S., Nicholson, G. et al. Purification and chemical characterization of staphyloferrin B, a hydrophilic siderophore from staphylococci. Biometals 6, 185–192 (1993). https://doi.org/10.1007/BF00205858
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00205858