Summary
Synthetic molecules that mimic the properties of the natural siderophores promise to become powerful tools in the exploration of microbial iron(III)-uptake phenomena. Such molecules can serve as probes to (i) establish the essential structural requirements for biological action, (ii) trace alternative reaction pathways and (iii) compare receptors of different biological origins. In this article a series of synthetic ferrichrome analogs will be described. The strategy adopted for the design and synthesis of these compounds will be outlined and their properties in vitro and in vivo examined. The growth promotion activity of these compounds inArthrobacter flavescens is used to map the ferrichrome receptor surface. Their activities towardsZea mays allow us to trace the plants' reductive iron(III) uptake routes. Potential applications of modified ferrichrome analogs for the isolation of ferrichrome receptors, the generation of fluorescent probes and ultimately new families of antibiotic or antifungal agents, will also be indicated.
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References
Adjimani JP, Emery T (1988) Structural aspects of iron transport inMycelia sterilia EP. 76. J Bacteriol 170:1377–1379
Borgias BA, Barclay SJ, Raymond KN (1986) Structural chemistry of gallium(III). J Coord Chem 15:109–123
Breslow R (1980) Biomimetic control of chemical selectivity. Acc Chem Res 13:170–177
Burnham BF, Neilands JB (1960) Studies on the metabolic function of the ferrichrome compounds. J Biol Chem 236:554–559
Cram DJ (1988) The design of molecular hosts, guests and their complexes. Science 240:760–767
Crowley DE, Reid CPP, Szaniszlo PJ (1987) Microbial siderophores as iron sources for plants. In: Winkelmann G, van der Helm D, Neilands JB (eds) Iron transport in microbes, plants and animals. pp 375–386
Dayhoff MO, Schwartz RM, Orcutt BC (1978) In: Dayhoff MO (ed) Atlas of protein sequence and structure, vol 5, Suppl 3. National Biomedical Research Foundation, pp 345–352
Ecker DJ, Matzanke BF, Raymond KN (1986) Recognition and transport of ferric enterobactin inEscherichia coli. J Bacteriol 167:666–673
Ecker DJ, Loomis LD, Cass ME, Raymond KN (1988) Substituted complexes of enterobactin and synthetic analogues as probes of the ferric-enterobactin receptor inE. coli. J Am Chem Soc 110:2457–2464
Emery T (1966) Initial steps in the biosynthesis of ferrichrome. Incorporation ofσ N-hydroxyornithine andσN-acetyl 'Nhydroxyornithine. Biochemistry 5:3694–3701
Emery T (1971) Role of ferrichrome as a ferric ionophore inUstilago spherogena. Biochemistry 10:1483–1488
Emery T, Emery L, Olsen RK (1984) Retrohydroxamate ferrichrome; A biomimetic analogue of ferrichrome. Biochem Biophys Res Commun 119:1191–1197
Harris WR, Raymond KN (1979) Ferric ion sequestering agents, 3. J Am Chem Soc 101:6534–6541
Hider RC (1984) Siderophore mediated absorption of iron. Struct Bonding 58:25–87
Kellogg RM (1982) Bioorganic modelling. Top Curr Chem 101:111–145
Kellogg RM (1984) Chiral macrocycles as reagents and catalysts. Angew Chem Int Ed Eng 23:782–794
Lehn J-M (1988) Supramolecular chemistry - scope and perspectives. Angew Chem 100:91–116
Leong J, Neilands JB, Raymond KN (1974) Coordination isomers of biological iron transport compounds III. Biochem Biophys Res Commun 60:1066–1071
Leong J, Neilands JB (1976) Mechanisms of siderophore iron transport in enteric bacteria. J Bacteriol 126:823–830
Mutzanke BF, Muller GI, Raymond KN (1984) Hydroxamate siderophore mediated iron uptake inE. coli; stereospecißc recognition of ferric rhodotorulic acid. Biochem Biophys Res Commun 121:922–930
Neilands JB (1984) Methodology of siderophores. Struct Bonding 58:1–24
Raymond KN, Carrano CJ (1979) Coordination chemistry and microbial iron transport. Acc Chem Res 12:183–190
Raymond KN, Mueller G, Matzanke BF (1984) Complexation of iron by siderophores. A review of their solution and structural chemistry and biological function. Top Curr Chem 123:49–102
Rebek J (1987) Model studies in molecular recognition. Science 235:1478–1484
Rebek J (1988) Recent progress in molecular recognition. Top Curr Chem 149:189–210
Shanzer A, Libman J, Lifson S, Felder CE (1986) Origin of the Fe3−-binding and conformational properties of enterobactin. J Am Chem Soc 108:7609–7619
Shanzer A, Libman J, Lazar R, Tor Y, Emery T (1988) Synthetic ferrichrome analogues with growth promotion activity for arthobacter flavescens. Biochem Biophys Res Commun 157:389–394
Tor Y, Libman J, Shanzer A, Lifson S (1987) Biomimetic ferric ion carriers. A chiral analog of enterobactin. J Am Chem Soc 109:6517–6518
Tor Y, Libman J, Shanzer A (1987) Biomimetic ferric ion carriers. A chiral analog of enterobactin. J Am Chem Soc 109:6518–6519
Van der Helm D, Baker JR, Eng-Wilmot DL, Hossain MB, Loghry RA (1980) Crystal structure of ferrichrome and a comparison with the structure of ferrichrome A. J Am Chem Soc 102:4224–4231
Winkelmann G (1979) Evidence for stereospecific uptake of iron chelates in fungi. FEBS Lett 97:43–46
Winkelmann G, Braun V (1981) Stereoselective recognition of ferrichrome by fungi and bacteria. FEMS Microbiol Lett 11:237–241
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Shanzer, A., Libman, J. Synthetic siderophores as biological probes. Biol Metals 2, 129–134 (1989). https://doi.org/10.1007/BF01142550
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DOI: https://doi.org/10.1007/BF01142550