Streptolydigin

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	7229-50-7 ;
PubChem CID	220508;
DrugBank	DB04785 ;
ChemSpider	16736035 ;
UNII	6MON4029Q8;
ChEBI	CHEBI:45773 ;
ChEMBL	ChEMBL1236068 ;
CompTox Dashboard (EPA)	DTXSID20905083 ;
Chemical and physical data
Formula	C32H44N2O9
Molar mass	600.709 g·mol−1
3D model (JSmol)	Interactive image;
	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

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.
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.
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.
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.

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[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.