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Other names
Bottromycin A(2); Bottromycic A2 acid, methyl ester
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
PubChem CID
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Properties | |
C42H62N8O7S | |
Molar mass | 823.05608 g.mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Bottromycin is a macrocyclic peptide with antibiotic activity. It was first discovered in 1957 as a natural product isolated from Streptomyces bottropensis.[1] It has been shown to inhibit methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococci (VRE) among other Gram-positive bacteria and mycoplasma.[2] Bottromycin is structurally distinct from both vancomycin, a glycopeptide antibiotic, and methicillin, a beta-lactam antibiotic.
Bottromycin binds to the A site of the ribosome and blocks the binding of aminoacyl-tRNA, therefore inhibiting bacterial protein synthesis.[3] Although bottromycin exhibits antibacterial activity in vitro, it has not yet been developed as a clinical antibiotic, potentially due to its poor stability in blood plasma.[2] To increase its stability in vivo, some bottromycin derivatives have been explored.[2]
The structure of bottromycin contains a macrocyclic amidine as well as a thiazole ring. The absolute stereochemistry at several chiral centers has been determined as of 2009.[4] In 2012, a three-dimensional solution structure of bottromycin was published.[5] The solution structure revealed that several methyl groups are on the same face of the structure.
Bottromycin falls within the ribosomally synthesized and post-translationally modified peptide class of natural product.[6]
Huo
was invoked but never defined (see the help page).