Bambermycin

Names

[ Name ]:
Bambermycin

[Synonym ]:
(2R)-3-{[{[(2R,3R,4R,5S,6S)-3-{[(2S,3R,4R,5S,6R)-3-Acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-methyl-5-({(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)carbamoyl]tetrahydro-2H-pyran-2-yl}oxy)tetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}methyl)tetrahydro-2H-pyran-2-yl]oxy}-6-carbamoyl-4-(carbamoyloxy)-5-hydroxy-5-methyltetrah
Moenomycine
MOENOMYCIN
menomycin
Bambermycine
BAMBERMYCIN
BAMBERMYCINS
flavophospholipol
Flavomycin
moenomycin a

Biological Activity

[Description]:

Moenomycin complex is a potent transglycosylase inhibitor. Moenomycin complex inhibits bacterial growth by blocking the transglycosylase activity of class A penicillin-binding proteins (PBPs)[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

Transglycosylase[1]

[References]

[1]. Cheng TJ, et al. Domain requirement of moenomycin binding to bifunctional transglycosylases and development of high-throughput discovery of antibiotics. Proc Natl Acad Sci U S A. 2008 Jan 15;105(2):431-6.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Molecular Formula ]:
C₆₉H₁₀₇N₄O₃₅P

[ Molecular Weight ]:
1582.583

[ Exact Mass ]:
1581.661377

[ PSA ]:
611.69000

[ LogP ]:
4.81

[ Index of Refraction ]:
1.615

[ Storage condition ]:
0-6°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QA3020000

CHEMICAL NAME :: Moenomycin

CAS REGISTRY NUMBER :: 11015-37-5

LAST UPDATED :: 198910

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,740,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,740,1978

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 600 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - smooth muscle relaxant (mechanism undefined, spasmolytic) Behavioral - wakefulness Behavioral - somnolence (general depressed activity)

REFERENCE :: AACHAX Antimicrobial Agents and Chemotherapy (1961-70). (Ann Arbor, MI) 1961-70. For publisher information, see AMACCQ. Volume(issue)/page/year: -,743,1965

Safety Information

[ Hazard Statements ]:
H413

[ Risk Phrases ]:
53

[ RIDADR ]:
UN 3077 9 / PGIII

[ RTECS ]:
QA3020000

Articles

Positive cooperativity between acceptor and donor sites of the peptidoglycan glycosyltransferase.

Biochem. Pharmacol. 93(2) , 141-50, (2015)

The glycosyltransferases of family 51 (GT51) catalyze the polymerization of lipid II to form linear glycan chains, which, after cross linking by the transpeptidases, form the net-like peptidoglycan ma...

Risk assessment of ciprofloxacin, flavomycin, olaquindox and colistin sulfate based on microbiological impact on human gut biota.

Regul Toxicol Pharmacol 53(3) , 209-16, (2009)

Trace levels of veterinary antibiotics that reside in livestock products may disturb the balance of human intestinal microbiota and impair the colonized barrier function, which is critical to protect ...

Effect of flavophospholipol on conjugation frequency between Escherichia coli donor and recipient pairs in vitro and in the chicken gastrointestinal tract.

J. Antimicrob. Chemother. 58(2) , 359-66, (2006)

To examine the ability of flavophospholipol to inhibit bacterial conjugation between Escherichia coli donor and recipient pairs in vitro and in day-of-hatch chickens.In vitro donor cultures were incub...