Anguibactin

Vibrio anguillarum FatA FatB FatC, FatD Anguibactin Crosa, 1997... 

Anguibactin (Fig. 24, 70) from Vibrio anguillarum 171) contains DHB condensed with Cys (stereochemistry not determined). It is accompanied by a biosynthetic by-product 311) without the histamine part as its methyl ester. 

An analogous set of studies demonstrated that acinetobactin from Acinetohacter baumannii (392) has actually the structure 77 shown in Fig. 27 and that the one originally proposed (Fig. 24, 78) is that of pre-acinetobactin. In contrast, the thiazoline ring of anguibactin (Fig. 24, 70) (see above Sect. 5) is stable. Acinetobactin forms a 1 1 complex with Fe ". ... 

Jalal MAF, Hossain MB, van der Hehn D, Sanders-Loehr J, Actis LA, Crosa JH (1989) Structure of Anguibactin, a Unique Plasmid-related Siderophore from Fish-pathogen Vibrio anguillarum. J Am Chem Soc 111 292... 

Bacterial siderophores are another class of widespread toxins produced by bacteria. On land, mycobactins and exophilins are the best-known representatives. Those found in the sea, aquachelins, marinobactins, anguibactin, vulnibactin, and aerobactin (Table 12.3.1) are amphiphilic. This is a property that has received great attention for drug delivery problems and in relation to recognition processes (Testa 2000), devising efBcient algorithms for computer calculation (Fisher 2000). 

Jalal, M.A.F. Hossain, M.B. van der Helm, D. Sanders-Loehr, J. Actis, L.A. Crosa, J.H. (1989) Structure of anguibactin, a unique plasmid-related bacterial siderophore from the fish pathogen Vibrio anguillarum. J. Am. Chem. Soc., Ill, 292-6. 

Marine bacteria are known to produce thiazoline-containing metabolites the antimitotic curacins and the metal chelators anguibactin and agrochelin. 

Anguibactin (470) is a unique siderophore (microbial iron-transport compound) isolated from iron-deficient cultures of a fish pathogenic bacterium, Vibrio anguillarum (378). The structure of 470 was determined by X-ray diffraction studies of its anhydro derivative. Another related compound copurified with 470 was identified as 2-(2, 3 -dihydroxyphenyl)-thiazoline-4-carboxyiic acid methyl ester (471) (379). 

Figure 4 Structures of siderophores with heterocyclic ligands (a) acinetohactin, (h) anguibactin, and (c) yersiniahactin...

Anguibactin, a siderophore of the fish pathogen, Vibrio anguillarum, is a virulence factor. When anguibactin was fed to a siderophore-deficient avirulent mutant of V. anguillarum, the mutant successfully established itself in the host fish [112]. 

Closely related to Anguibactin, A-01722. Isol. from low-iron cultures of Acinetobacter baumannii ATCC 19606. Siderophore. 

Vibrio anguillarum Fish Anguibactin Siderophore Jalal eta/., 1989... 

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