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74675 Sigma-Aldrich

Novobiocin sodium salt

≥93% (HPLC)

  • CAS Number 1476-53-5

  • Empirical Formula (Hill Notation) C31H35N2NaO11

  • Molecular Weight 634.61

  •  Beilstein/REAXYS Number 3892910

  •  EC Number 216-023-6

  •  NACRES NA.85

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Properties

Related Categories Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics N-S, Antibiotics by Application,
Quality Level   200
assay   ≥93% (HPLC)
form   powder
optical activity   [α]20/D −48±3°, c = 1% in ethanol
color   white to faint beige
solubility   H2O: soluble
Mode of action   DNA synthesis | interferes
  enzyme | inhibits
antibiotic activity spectrum   Gram-positive bacteria
storage temp.   2-8°C
SMILES string   [Na+].CO[C@@H]1[C@@H](OC(N)=O)[C@@H](O)[C@H](Oc2ccc3C([O-])=C(NC(=O)c4ccc(O)c(C\C=C(\C)C)c4)C(=O)Oc3c2C)OC1(C)C
InChI   1S/C31H35N2O11.Na/c1-14(2)7-8-16-13-17(9-11-19(16)34)27(37)33-21-22(35)18-10-12-20(15(3)24(18)42-28(21)38)41-29-23(36)25(43-30(32)39)26(40-6)31(4,5)44-29;/h7,9-13,23,25-26,29,34,36H,8H2,1-6H3,(H2,32,39)(H,33,37);/q-1;+1
InChI key   AXOUUAINTJNFRS-UHFFFAOYSA-N

Description

General description

Chemical structure: coumarin-glycoside

Application

Novobiocin is used to study heat shock protein inhibition and to produce positively supercoiled plasmid DNA. It is an inhibitor of bacterial DNA gyrase and eukaryotic DNA topoisomerase. It also is an inhibitor of retrovirus RNA-dependent DNA-polymerase.

For the production of positively supercoiled plasmid DNA. Inhibitor of bacterial DNA gyrase and eukaryotic DNA topoisomerase. Inhibitor of retrovirus RNA-dependent DNA-polymerase.

Biochem/physiol Actions

Novobiocin inhibits DNA synthesis by inhibiting bacterial DNA gyrase targeting the GyrB subunit of the enzyme involved in energy transduction. Novobiocin acts as a competitive inhibitors of the ATPase reaction catalysed by GyrB . It is also a Hsp90 inhibitor . Antimicrobial spectrum: Gram-positive bacterial.

Mode of Action: Inhibits DNA synthesis by inhibiting the enzyme Topoisomerase II.
Antimicrobial spectrum: Gram-positive bacterial.

Packaging

1g, 5g

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Light sensitive. Store under inert gas. Keep in a dry place.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 1
RTECS 
RD5425000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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