Streptolydigin

Streptolydigin

Systematic (IUPAC) name
2-[4-[6-(1,6-dimethylspiro[8,9-dioxabicyclo[3.3.1]non-3-ene-2,2'-oxirane]-7
Identifiers
CAS Number	7229-50-7
ATC code	none
PubChem	CID 220508
DrugBank	DB04785
ChemSpider	16736035
ChEBI	CHEBI:45773
ChEMBL	CHEMBL1236068
Chemical data
Formula	C32H44N2O9
Molar mass	600.708 g/mol
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+ Key:KVTPRMVXYZKLIG-NCFIBNQNSA-N
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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.

References

1. Tuske, S.; Sarafianos, S.; Wang, X.; Hudson, B.; Sineva, E.; Mukhopadhyay, J.; Birktoft, J.; Leroy, O.; Ismail, S.; Clark, A.; Dharia, C.; Napoli, A.; Laptenko, O.; Lee, J.; Borokhov, S.; Arnold, E.; Ebright, R. (2005). "Inhibition of bacterial RNA polymerase by streptolydigin: stabilization of a straight-bridge-helix active-center conformation". Cell 122 (4): 541–552. doi:10.1016/j.cell.2005.07.017. PMC 2754413. PMID 16122422.
2. Temiakov, D; Zenkin, N; Vassylyeva, M. N.; Perederina, A; Tahirov, T. H.; Kashkina, E; Savkina, M; Zorov, S; Nikiforov, V; Igarashi, N; Matsugaki, N; Wakatsuki, S; Severinov, K; Vassylyev, D. G. (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, D. G.; Vassylyeva, M. N.; Zhang, J; Palangat, M; Artsimovitch, I; Landick, R (2007). "Structural basis for substrate loading in bacterial RNA polymerase". Nature 448 (7150): 163–8. doi:10.1038/nature05931. PMID 17581591.
4. Tuske, S.; Sarafianos, S.; Wang, X.; Hudson, B.; Sineva, E.; Mukhopadhyay, J.; Birktoft, J.; Leroy, O.; Ismail, S.; Clark, A.; Dharia, C.; Napoli, A.; Laptenko, O.; Lee, J.; Borokhov, S.; Arnold, E.; Ebright, R. (2005). "Inhibition of bacterial RNA polymerase by streptolydigin: stabilization of a straight-bridge-helix active-center conformation". Cell 122 (4): 541–552. doi:10.1016/j.cell.2005.07.017. PMC 2754413. PMID 16122422.