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Merck
CN

C9270

Coumermycin A1

Synonym(s):

Notomycin A1

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About This Item

Empirical Formula (Hill Notation):
C55H59N5O20
CAS Number:
4434-05-3
Molecular Weight:
1110.08
UNSPSC Code:
51102829
NACRES:
NA.85
PubChem Substance ID:
329775201
MDL number:
MFCD00057312
Beilstein/REAXYS Number:
470805

Key Documents

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InChI

1S/C55H59N5O20/c1-21-12-16-29(57-21)48(67)77-42-38(63)52(79-54(6,7)44(42)71-10)73-31-18-14-26-36(61)34(50(69)75-40(26)24(31)4)59-46(65)28-20-56-33(23(28)3)47(66)60-35-37(62)27-15-19-32(25(5)41(27)76-51(35)70)74-53-39(64)43(45(72-11)55(8,9)80-53)78-49(68)30-17-13-22(2)58-30/h12-20,38-39,42-45,52-53,56-58,61-64H,1-11H3,(H,59,65)(H,60,66)/t38-,39-,42+,43+,44-,45-,52-,53-/m1/s1

SMILES string

CO[C@@H]1[C@@H](OC(=O)c2ccc(C)[nH]2)[C@@H](O)[C@H](Oc3ccc4C(O)=C(NC(=O)c5c[nH]c(C(=O)NC6=C(O)c7ccc(O[C@@H]8OC(C)(C)[C@H](OC)[C@@H](OC(=O)c9ccc(C)[nH]9)[C@H]8O)c(C)c7OC6=O)c5C)C(=O)Oc4c3C)OC1(C)C

InChI key

WTIJXIZOODAMJT-DHFGXMAYSA-N

form

powder

solubility

DMSO: 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

mode of action

DNA synthesis | interferes, enzyme | inhibits

General description

Chemical structure: coumarin-glycoside

Application

Coumermycin A1 is an aminocoumarin antibiotic used to study processes such as DNA replication, transcription, and recombination that involve DNA topoisomerase II activity. It has been used to treat Staphylococcus aureus endocarditis in the rat model and to study the effect of coumermycin A1 on the expression of 67 fusions in Salmonella typhimurium. .

Biochem/physiol Actions

Coumermycin A1 inhibits DNA Gyrase which thereby inhibits cell division in bacteria.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
SLBZ7154
SLBT5569
SLBN6743V
SLBC8762V
061M1846V

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Carl J Balibar et al.
Chemistry & biology, 14(6), 679-690 (2007-06-23)
The last stages of assembly of the aminocoumarin antibiotics, clorobiocin and coumermycin A(1), which target the GyrB subunits of bacterial DNA gyrase, involve enzymatic transfer of the pyrrolyl-2-carbonyl acyl group from a carrier protein (CloN1/CouN1) to the 3'-OH of the
Michelle Pacholec et al.
Biochemistry, 44(45), 14969-14976 (2005-11-09)
During the biosynthesis of the streptomycete aminocoumarin antibiotics novobiocin and the dimeric coumermycin A(1), the bicyclic coumarin scaffold is C-methylated adjacent to the phenolic oxygen. The SAM-dependent C-methyltransferases NovO and CouO have been heterologously expressed and purified from Escherichia coli
Manuel Wolpert et al.
Chembiochem : a European journal of chemical biology, 9(4), 603-612 (2008-02-22)
Many secondary metabolites of clinical importance have been isolated from different Streptomyces species. As most of the natural producers remain difficult to handle genetically, heterologous expression of an entire biosynthetic gene cluster in a well characterised host allows improved possibilities
Andreas I Papadakis et al.
Genesis (New York, N.Y. : 2000), 49(9), 743-749 (2011-03-26)
Phosphorylation of the alpha (α) subunit of the eukaryotic initiation factor 2 (eIF2) at serine 51 is an important mechanism of translational control in response to various forms of environmental stress. In metazoans, eIF2α phosphorylation is mediated by four kinases
Ya-Han Hsu et al.
Nucleic acids research, 34(10), 3128-3138 (2006-06-08)
We explored the existence of nucleoid DNA loops in Escherichia coli by studying the distribution of bacterial type II topoisomerases (Topo IIs). Norfloxacin-induced high molecular weight (HMW) DNA fragmentation of nucleoid, an event reminiscent of the excision of eukaryotic chromosomal
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