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SML0285

Sigma-Aldrich

Pleuromutilin

≥95%

Synonym(s):

Drosophilin B, Mutilin 14-glycolate, NSC 121145

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About This Item

Empirical Formula (Hill Notation):
C22H34O5
CAS Number:
Molecular Weight:
378.50
EC Number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥95%

form

powder

optical activity

[α]/D +30 to +40° (c=1; CH2Cl2)

color

white to beige

solubility

DMSO: >10 mg/mL (warmed)

shipped in

wet ice

storage temp.

−20°C

SMILES string

C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]3C)OC(=O)CO

InChI

1S/C22H34O5/c1-6-20(4)11-16(27-17(25)12-23)21(5)13(2)7-9-22(14(3)19(20)26)10-8-15(24)18(21)22/h6,13-14,16,18-19,23,26H,1,7-12H2,2-5H3/t13-,14+,16-,18+,19+,20-,21+,22+/m1/s1

InChI key

ZRZNJUXESFHSIO-BKUNHTPHSA-N

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Biochem/physiol Actions

Pleuromutilin is a diterpene that acts against gram positive bacteria and mycoplasm. It is present in Pleurotus mutilus and Pleurotus passecherianus. Pleuromutilin exhibits its antibacterial action by interfering with the prokaryotic 70S ribosomal subunit and inactivates initiation complex. Pleuromutilin is useful in treating mycoplasma infections in animals.
Pleuromutilin is an antibiotic natural product that inhibits bacterial protein synthesis by binding to bacterial ribosomes in the peptidyl transferase center and inhibiting peptide bond formation.

Pictograms

Exclamation markEnvironment

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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The enterococcal ABC transporter gene lsa(E) confers combined resistance to lincosamides, pleuromutilins and streptogramin A antibiotics in methicillin-susceptible and methicillin-resistant Staphylococcus aureus.
Sarah Wendlandt et al.
The Journal of antimicrobial chemotherapy, 68(2), 473-475 (2012-10-11)
A dialdehyde cyclization cascade: an approach to pleuromutilin.
Matthew D Helm et al.
Angewandte Chemie (International ed. in English), 48(49), 9315-9317 (2009-11-11)
Izabela Karpiuk et al.
Przeglad epidemiologiczny, 66(4), 567-573 (2012-01-01)
Development of new mechanisms of resistance and relatively easy and fast transferring of resistance genes between cells have resulted in emergence of large number of multi-drug resistant bacteria in recent years. Therefore, it is important to intensively search for new
Encyclopedia of Food Sciences and Nutrition (Second Edition), 575-575 (2014)
Lykke H Hansen et al.
Antimicrobial agents and chemotherapy, 56(7), 3563-3567 (2012-05-02)
The cfr gene encodes the Cfr methyltransferase that methylates a single adenine in the peptidyl transferase region of bacterial ribosomes. The methylation provides resistance to several classes of antibiotics that include drugs of clinical and veterinary importance. This paper describes

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