Streptolydigin

Streptolydigin (Stl) is an antibiotic that works by inhibiting nucleic acid chain elongation by binding to RNA polymerase, thus inhibiting RNA synthesis inside a cell.[1][2][3] Streptolydigin inhibits bacterial RNA polymerase, but not eukaryotic RNA polymerase.[4] It has antibacterial activity against a number of Gram positive bacteria.

Streptolydigin
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 2-[4-[6-(1,6-dimethylspiro[8,9-dioxabicyclo[3.3.1]non-3-ene-2,2'-oxirane]-7
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC32H44N2O9
Molar mass600.709 g·mol−1
3D model (JSmol)
SMILES
  • CNC(=O)C(C)C2C(=O)/C(C(=O)N2C1CCC(O)C(C)O1)=C(\O)/C=C/C(/C)=C/C(C)C5OC4(C)OC(\C=C/C34CO3)C5C
InChI
  • InChI=1S/C32H44N2O9/c1-16(14-17(2)28-18(3)23-12-13-32(15-40-32)31(6,42-23)43-28)8-9-22(36)25-27(37)26(19(4)29(38)33-7)34(30(25)39)24-11-10-21(35)20(5)41-24/h8-9,12-14,17-21,23-24,26,28,35-36H,10-11,15H2,1-7H3,(H,33,38)/b9-8+,16-14+,25-22+ Y
  • Key:KVTPRMVXYZKLIG-NCFIBNQNSA-N Y
 NY (what is this?)  (verify)

References
  1. Tuske S, Sarafianos SG, Wang X, Hudson B, Sineva E, Mukhopadhyay J, et al. (August 2005). "Inhibition of bacterial RNA polymerase by streptolydigin: stabilization of a straight-bridge-helix active-center conformation". Cell. 122 (4): 541–52. doi:10.1016/j.cell.2005.07.017. PMC 2754413. PMID 16122422.
  2. Temiakov D, Zenkin N, Vassylyeva MN, Perederina A, Tahirov TH, Kashkina E, et al. (September 2005). "Structural basis of transcription inhibition by antibiotic streptolydigin". Molecular Cell. 19 (5): 655–66. doi:10.1016/j.molcel.2005.07.020. PMID 16167380.
  3. Vassylyev DG, Vassylyeva MN, Zhang J, Palangat M, Artsimovitch I, Landick R (July 2007). "Structural basis for substrate loading in bacterial RNA polymerase". Nature. 448 (7150): 163–8. arXiv:0707.3064. Bibcode:2007Natur.448..163V. doi:10.1038/nature05931. PMID 17581591. S2CID 4320480.
  4. Tuske S, Sarafianos SG, Wang X, Hudson B, Sineva E, Mukhopadhyay J, et al. (August 2005). "Inhibition of bacterial RNA polymerase by streptolydigin: stabilization of a straight-bridge-helix active-center conformation". Cell. 122 (4): 541–52. doi:10.1016/j.cell.2005.07.017. PMC 2754413. PMID 16122422.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.