Bacterial siderophore

E. Jurkevitch, Y. Hadar, and Y. Chen, Involvement of bacterial siderophores in the remedy of lime-induced chlorosis in peanut. Soil Sci. Soc. Am. J. 52 1032 (1988). 

Fig. 31. Bacterial siderophores that evade recognition by side-rocalin, salmochelin S4, and petrobactin.

Bacterial siderophores are typically small peptidic molecules, which contain side chains and functional groups that can provide high-affinity ligands for coordination of ferric ions. The structures of some siderophores are shown in Drechsel and Jung [142]. Siderophore synthesis occurs via enzymatic assembly by nonribosomal peptide synthetases [144], In bacteria, siderophore synthesis is... 

Liermann LJ, Kalinowski BE, Brantley SL, Ferry JG (2000) Role of bacterial siderophores in dissolution of hornblende. Geochim Cosmochim Acta 64 587-602... 

Demange P, Bateman A, Mertz C, Dell A, Piemont Y, Abdallah MA (1990) Bacterial Siderophores Structure of Pyoverdins Pt, Siderophores of Pseudomonas tolaasii NCPPB 2192, and Pyoverdins Pf, Siderophores of Pseudomonas fluorescens CCM 2798. Identification of an Unusual Natural Amino Acid. Biochemistry 29 11041... 

Demange P, Wendenbaum S, Bateman A, Dell A, Meyer JM, Abdallah MA (1986) Bacterial Siderophores Structure of Pyoverdins and Related Compounds. In Swinburne TR (ed) Iron, Siderophores, and Plant Diseases. Plenum, New York, p 131... 

Sansinenea E, Ortiz A (2009) Bacterial Siderophores Containing a Thiazoline Ring. Mini-Rev Org Chem 6 120... 

Wong-Lun-Sang S, Bemardini JJ, Hennard C, Kyslik P, Dell A, Abdallah MA (1996) Bacterial Siderophores Structure Elucidation, 2D H and C NMR Assignments of Pyoverdins Produced by Pseudomonas floorescens CHAO. Tetrahedron Lett 37 3329... 

Alterobactin A is a cyclic mono-catechol-bis-hydroxycarboxylate bacterial siderophore with an extremely high affinity for iron(III) (see Table 12). On hydrolysis n the absence of iron) it gives an acyclic derivative which forms a bis-ligand iron(III) complex. ... 

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. 

The competition between transferrin and infectious organisms is a fascinating topic. During infection, the mammalian host will attempt to diminish the iron available to the bacterium. The iron levels in the blood decrease and the iron stores in the liver increase. The observation that siderophore synthesis is sharply reduced at temperatures just over 37 °C may mean that the physiological function of fever is to depress bacterial siderophore synthesis, as shown for a rabbit pathogen, Pseudomonas multocida.1203... 

For a synthesis of Cephalosporin C Woodward and co-workers required a protecting group that could be removed under mild and highly specific conditions. From this work, the 2,23-trichloroethyl (TCE) group was bom and its specific removal on treatment with zinc in acetic acid was the concluding step to their pioneering synthesis.193 More recently, zinc and 1 M ammonium acetate in THF has also be used.194 The group is still employed extensively in peptide synthesis as shown in a late step in a synthesis of the bacterial siderophore Alterobactin A [Scheme 6.83].195... 

The Mtr group was used to protect an arginine residue in a solution phase synthesis of the bacterial siderophore Alterobactin A.510 In the closing stages of the synthesis, an ester function was first unleashed from intermediate 257.1 [Scheme 8,257] followed by the selective deprotection of a terminal iV-Boc group with trifluoroacetic acid Note the preservation of the Mtr group and the... 

Yoshida T., Hayashi K., and Ohmoto H. (2002) Dissolution of iron hydroxides by marine bacterial siderophore. Chem. Geol. 184(1-2), 1-9. 

The bacterial siderophores parabactin and compound II secreted by Paracoccus denitrificans have been shown to inhibit the growth of leukaemia cells in culture and in experimental animals. They also appear capable of inhibiting the replication of RNA viruses. 

Fig. 19.26 Three types of bacterial siderophores (a) desferrichrome (b) desferrioxamine B (cl enierobactin.

A large proportion of bacterial siderophore uptake studies were centered on enteric bacteria as typified by E. coli and S. typhimurium. These bacteria possess a cell wall consisting of an outer membrane layer and a peptidoglycan layer. The former acts as a molecular sieve-type barrier, and the latter confers mechanical stability. Thus, the metabolically active cytoplasmic membrane is protected against bile salts and hydrolytic enzymes found in the mammalian gastrointestinal tract. The outer membrane... 

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