The configuration of the chiral carbon atoms in staphyloferrin A and analysis of the transport properties in <Emphasis Type="Italic">Staphylococcus aureus</Emphasis> |
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Authors: | Hartmut?Drechsel Email author" target="_blank">Günther?WinkelmannEmail author |
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Institution: | 1.Institut für Mikrobiologie, Mikrobiologie & Biotechnologie,Universit?t Tübingen,Tübingen,Germany |
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Abstract: | Staphyloferrin A, the iron-transporting siderophore of Staphylococci, contains two citric acid residues linked to a D-ornithine backbone, having thus three chiral centers. While the chirality of the backbone can be determined after hydrolysis,
the chirality of the two citryl residues can only be determined from the intact staphyloferrin A molecule by circular dichroism
spectra. The chirality of the quarternary carbon atoms of citryl residues in fungal rhizoferrin and bacterial enantio-rhizoferrin have been determined previously to be R,R and S,S respectively. The present investigation shows that of the three
chiral centers in staphyloferrin A, the citryl residues can be assigned an S,S-configuration by comparison with synthetic
analogs, confirming a common chirality among the bacterial enantio-rhizoferrin and staphyloferrin A. This suggests that the bacterial carboxylates originate from a common biosynthetic pathway
leading to an S,S-configuration, while the fungal rhizoferrin possessing an R,R-configuration must have a different biosynthetic
origin. Growth promotion tests with staphylococci revealed that the S,S-configuration of staphyloferrin A and enantio-rhizoferrin enabled iron uptake, while the fungal rhizoferrin with R,R-configuration was not utilized.
Published online December 2004 |
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Keywords: | siderophores iron staphyloferrin rhizoferrin chirality stereochemistry |
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