Albomycin

Albomycin δ2 bound to iron

Albomycins are a group of naturally occurring antibiotics belonging to the class of sideromycins, which are "compounds composed of iron carriers called siderophores linked to antibiotic moieties". They are particularly effective against Gram-negative bacteria of the family Enterobacteriaceae and few Gram-positive bacteria such s Streptococcus pneumoniae, Bacillus subtilis and Staphylococcus aureus.[1][2] In 2000 a group of scientists from SmithKline Beecham Pharmaceuticals, UK reported that the antibiotic part of albomycin in vitro can inhibit seryl t-RNA synthetase from both eukaryotic and prokaryotic representatives.[3]

Structure

Albomycins are naturally occurring sideromycins produced by some streptomycetes. The siderophore part of albomycin δ2 is similar to ferrichrome. It contains three molecules of δ-N-hydroxy-δ-N-acetyl ornithine linked to a serine, all by peptide linkage. The C-terminus of the serine is linked to another serine attached to the antibiotically active 4’-thio (N4-carbamoyl-3-methyl) cytidine moiety. The trihydroxamate part serves the siderophore function as it can trap Fe+3 and is essential for active transport of the antibiotic. Iron-free albomycin δ2 has a molecular weight of 992 Da, and when loaded with iron it is 1045 Da.[4]

Albomycin δ1
Albomycin δ2
Albomycin ε

References

  1. ↑ Pramanik, A.; Stroeher, U.; Krejci, J.; Standish, A.; Bohn, E.; Paton, J.; Autenrieth, I.; Braun, V. (October 2007). "Albomycin is an effective antibiotic, as exemplified with Yersinia enterocolitica and Streptococcus pneumoniae". International Journal of Medical Microbiology. 297 (6): 459–469. doi:10.1016/j.ijmm.2007.03.002. PMID 17459767.
  2. ↑ Pramanik, A.; Braun, V. (June 2006). "Albomycin Uptake via a Ferric Hydroxamate Transport System of Streptococcus pneumoniae R6". Journal of Bacteriology. 188 (11): 3878–3886. doi:10.1128/jb.00205-06. PMC 1482914. PMID 16707680.
  3. ↑ Stefanska, Anna L.; Fulston, Mark; Houge-Frydrych, Catherine S.V; Jones, Jo J.; Warr, Stephen R. (June 2000). "A Potent Seryl tRNA Synthetase Inhibitor SB-217452 Isolated from a Streptomyces species". The Journal of Antibiotics. 53 (12): 1346–1353. doi:10.7164/antibiotics.53.1346. PMID 11217799.
  4. ↑ Hartmann, Anton; Fiedler, Hans-Peter; Braun, Volkmar (September 1979). "Uptake and Conversion of the Antibiotic Albomycin by Escherichia coli K-12". European Journal of Biochemistry. 99 (3): 517–524. doi:10.1111/j.1432-1033.1979.tb13283.x. PMID 387415.
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