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C9270

Coumermycin A1

Name: Coumermycin A1
Brand: SIGMA

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

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form

powder

solubility

DMSO: 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

mode of action

DNA synthesis | interferes, enzyme | inhibits

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

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

InChI key

WTIJXIZOODAMJT-DHFGXMAYSA-N

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

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

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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Covalent CouN7 enzyme intermediate for acyl group shuttling in aminocoumarin biosynthesis.

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

CouO and NovO: C-methyltransferases for tailoring the aminocoumarin scaffold in coumermycin and novobiocin antibiotic biosynthesis.

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

Drug-sensing hydrogels for the inducible release of biopharmaceuticals.

Martin Ehrbar et al.

Nature materials, 7(10), 800-804 (2008-08-12)

Drug-dependent dissociation or association of cellular receptors represents a potent pharmacologic mode of action for regulating cell fate and function. Transferring the knowledge of pharmacologically triggered protein-protein interactions to materials science will enable novel design concepts for stimuli-sensing smart hydrogels.

Distribution of gyrase and topoisomerase IV on bacterial nucleoid: implications for nucleoid organization.

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

Assembly and heterologous expression of the coumermycin A1 gene cluster and production of new derivatives by genetic engineering.

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

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Global Trade Item Number

SKU	GTIN
C9270-10MG	04061833530443
C9270-50MG	04061832990996
C9270-5MG	04061832991009

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