Pleuromulin
Pleuromulin Basic information
- Product Name:
- Pleuromulin
- Synonyms:
-
- PLEUROMULIN
- PLEUROMUTILIN
- a4014c
- antibioticbc757
- bc757
- drosopholinb
- glycolicacid,8-esterwithoctahydro-5,8-dihydroxy-4,6,9,10-tetramethyl-6-viny
- l-3a,9-propano-3ah-cyclopentacycloocten-1(4h)-one
- CAS:
- 125-65-5
- MF:
- C22H34O5
- MW:
- 378.5
- EINECS:
- 204-747-5
- Product Categories:
-
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Mol File:
- 125-65-5.mol
Pleuromulin Chemical Properties
- Melting point:
- 170-1710C
- Boiling point:
- 482.8±45.0 °C(Predicted)
- alpha
- D24 +20° (c = 3 in abs ethanol)
- Density
- 1.15±0.1 g/cm3(Predicted)
- storage temp.
- -20°C Freezer
- solubility
- DMSO: >10mg/mL (warmed)
- pka
- 12.91±0.10(Predicted)
- form
- powder
- color
- white to beige
- optical activity
- [α]/D +30 to +40° (c=1; CH2Cl2)
- InChIKey
- YSBXUHAJXRCCET-BKUNHTPHSA-N
- SMILES
- C(O[C@@H]1C[C@](C=C)(C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@]2([H])C(=O)CC3)(=O)CO
Pleuromulin Usage And Synthesis
Description
Pleuromutilin is an antibiotic derived from the fungus Clitopilus that inhibits bacterial protein synthesis by binding to bacterial ribosomes in the peptidyl transferase component of the 50S subunit and inhibiting peptide bond formation.
Chemical Properties
Pleuromulin is Crystalline Solid
Uses
Antibiotic substance produced by the basidiomycetes Pleurotus mutilus.
Uses
Pleuromutilin is a diterpene produced by several species of basidomycete, notably the genus Pleurotus, discovered in 1951. Pleuromutilin is a potent and highly selective antibiotic active against a range of Gram positive bacteria, with no cross resistance to existing antibiotic classes due to its unique mode of action. Pleuromutilin inhibits protein synthesis by binding to domain V of 23S rRNA and this has led to the development of many semi-synthetic analogues as new generation antibiotics, such as tiamulin and retapamulin.
Pleuromutilins such as tiamulin and valnemulin have been used for some time in veterinary medicine to treat swine infections. More recently a semisynthetic pleuromutilin, retapamulin, has been introduced as a topical treatment for Gram-positive infections in humans. Pleuromutilins inhibit the peptidyl transferase activity of the bacterial 50S ribosomal subunit by binding to the A site.
References
[1]. kilaru s, collins cm, hartley aj, et al. establishing molecular tools for genetic manipulation of the pleuromutilin-producing fungus clitopilus passeckerianus. appl environ microbiol. 2009 nov;75(22):7196-204.
[2]. long ks, hansen lh, jakobsen l, et al. interaction of pleuromutilin derivatives with the ribosomal peptidyl transferase center. antimicrob agents chemother. 2006 apr;50(4):1458-62.
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