streptolydigin

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 470471049

| IUPAC_name = 2-[4-[6-(1,6-dimethylspiro[8,9-dioxabicyclo[3.3.1]non-3-ene-2,2'-oxirane]-7

| image = Streptolydigin.png

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 7229-50-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 6MON4029Q8

| ATC_prefix = none

| ATC_suffix =

| ATC_supplemental =

| PubChem = 220508

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB04785

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 16736035

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1236068

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 45773

| C=32 | H=44 | N=2 | O=9

| 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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+

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = KVTPRMVXYZKLIG-NCFIBNQNSA-N

}}

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.{{cite journal | vauthors = Tuske S, Sarafianos SG, Wang X, Hudson B, Sineva E, Mukhopadhyay J, Birktoft JJ, Leroy O, Ismail S, Clark AD, Dharia C, Napoli A, Laptenko O, Lee J, Borukhov S, Ebright RH, Arnold E | display-authors = 6 | title = Inhibition of bacterial RNA polymerase by streptolydigin: stabilization of a straight-bridge-helix active-center conformation | journal = Cell | volume = 122 | issue = 4 | pages = 541–52 | date = August 2005 | pmid = 16122422 | pmc = 2754413 | doi = 10.1016/j.cell.2005.07.017 }}{{cite journal | vauthors = Temiakov D, Zenkin N, Vassylyeva MN, Perederina A, Tahirov TH, Kashkina E, Savkina M, Zorov S, Nikiforov V, Igarashi N, Matsugaki N, Wakatsuki S, Severinov K, Vassylyev DG | display-authors = 6 | title = Structural basis of transcription inhibition by antibiotic streptolydigin | journal = Molecular Cell | volume = 19 | issue = 5 | pages = 655–66 | date = September 2005 | pmid = 16167380 | doi = 10.1016/j.molcel.2005.07.020 | doi-access = free }}{{cite journal | vauthors = Vassylyev DG, Vassylyeva MN, Zhang J, Palangat M, Artsimovitch I, Landick R | s2cid = 4320480 | title = Structural basis for substrate loading in bacterial RNA polymerase | journal = Nature | volume = 448 | issue = 7150 | pages = 163–8 | date = July 2007 | pmid = 17581591 | doi = 10.1038/nature05931 | arxiv = 0707.3064 | bibcode = 2007Natur.448..163V }} Streptolydigin inhibits bacterial RNA polymerase, but not eukaryotic RNA polymerase.{{cite journal | vauthors = Tuske S, Sarafianos SG, Wang X, Hudson B, Sineva E, Mukhopadhyay J, Birktoft JJ, Leroy O, Ismail S, Clark AD, Dharia C, Napoli A, Laptenko O, Lee J, Borukhov S, Ebright RH, Arnold E | display-authors = 6 | title = Inhibition of bacterial RNA polymerase by streptolydigin: stabilization of a straight-bridge-helix active-center conformation | journal = Cell | volume = 122 | issue = 4 | pages = 541–52 | date = August 2005 | pmid = 16122422 | pmc = 2754413 | doi = 10.1016/j.cell.2005.07.017 }} It has antibacterial activity against a number of Gram positive bacteria.{{cn|date=January 2023}}