Bottromycin

Title: Bottromycin
CAS Registry Number: 1393-68-6
Additional Names: B-mycin
Literature References: A complex of five antibiotics of which the main active component is bottromycin A2. Produced by Streptomyces bottropensis and S. canadensis: Waisvisz et al., J. Am. Chem. Soc. 79, 4520, 4522, 4524 (1957); Miller et al., Antimicrob. Agents Chemother. 1967, 407. Production: GB 762736 (1956 to Koninklijke Nederlandsche Gist en Spiritus-Fabriek); Umesawa et al., JP 68 10998 (1968 to Microbiochem. Res. Found.), C.A. 69, 85439x (1968); Hata et al., US 3650904 (1972). Partial structure: Waisvisz, Hoeven, J. Am. Chem. Soc. 80, 38 (1958). Sepn and structures of bottromycins A1, A2, and B: Nakamura et al., J. Antibiot. 18A, 47, 60 (1965); 19A, 10 (1966). Isoln and characterization of bottromycins A2, B2, C2: Nakamura et al., ibid. 20A, 1 (1967). Revised structure of bottromycin A2: Takahashi et al., ibid. 29A, 1120 (1976); D. Schipper, ibid. 36A, 1076 (1983). Mode of action of bottromycin A2: T. Otaka, A. Kaji, J. Biol. Chem. 251, 2299 (1976); eidem, FEBS Lett. 123, 173 (1981).
Derivative Type: Bottromycin A2
Additional Names: Bottromycic A2 acid methyl ester
Molecular Formula: C42H62N8O7S
Molecular Weight: 823.06
Percent Composition: C 61.29%, H 7.59%, N 13.61%, O 13.61%, S 3.90%
Botulin Toxins Bradycor Bradykinin Brain Natriuretic Peptide Brallobarbital


Bottromycin
Chemical structure of bottromycin A2.png
Identifiers
CAS number 15005-62-6
PubChem 3081434
ChemSpider 26365309
Jmol-3D images Image 1
Properties
Molecular formula C42H62N8O7S
Molar mass 823.06 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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, an aminoglycoside 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.