A bacterial DNA gyrase inhibitor
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(R)-Gyramide A (hydrochloride)

Item No. 18528

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-fluoro-2-methyl-N-[(3R)-1-[[4-(1-methylethoxy)phenyl]methyl]-3-pyrrolidinyl]-benzenesulfonamide, monohydrochloride
CAS Number
1793050-70-0
Synonyms
  • (R)-534F6
Molecular Formula
C21H27FN2O3S • HCl
Formula Weight
443.0
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mLDMSO: 50 mg/mLEthanol: 50 mg/mLEthanol:PBS(pH 7.2) (1:1): 0.5 mg/mL
λmax
229, 275, 282 nm
SMILES
CC(C)OC1=CC=C(CN2CC[C@@H](NS(C3=C(C)C=CC(F)=C3)(=O)=O)C2)C=C1.Cl
InChi Code
InChI=1S/C21H27FN2O3S.ClH/c1-15(2)27-20-8-5-17(6-9-20)13-24-11-10-19(14-24)23-28(25,26)21-12-18(22)7-4-16(21)3;/h4-9,12,15,19,23H,10-11,13-14H2,1-3H3;1H/t19-;/m1./s1
InChi Key
LLHBXQVGBTVEDP-FSRHSHDFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    (R)-Gyramide A is a bacterial DNA gyrase inhibitor that disrupts supercoiling activity with an IC50 value of 3.3 µM.1 It does not affect the closely related enzyme topoisomerase IV.2 (R)-Gyramide A demonstrates antibacterial activity against E. coli, P. aeruginosa, and S. enterica (MICs range from 10-80 µM).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Foss, M.H., Hurley, K.A., Sorto, N.A., et al. N-Benzyl-3-sulfonamidopyrrolidines are a new class of bacterial DNA gyrase inhibitors. ACS Med. Chem. Lett. 2(4), 289-292 (2011).

    2. Rajendram, M., Hurley, K.A., Foss, M.H., et al. Gyramides prevent bacterial growth by inhibiting DNA gyrase and altering chromosome topology. ACS Chem. Biol. 9(6), 1312-1319 (2014).