Novobiocin

• CAT Number: R060001
• CAS Number: 303-81-1
• Molecular Formula: C31H36N2O11
• Molecular Weight: 612.632
• Purity: ≥95%
• Synonyms: N-[7-[[3-O-(aminocarbonyl)-6-deoxy-5-C-methyl-4-O-methyl-α-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl]-4-hydroxy-3-(3-methyl-2-buten-1-yl)benzamide; ?N-[7-[[3-O-(aminocarbonyl)-6-deoxy-5-C-methyl-4-O-methyl-α-L-lyxo-hexop
• Storage: Store at -80C
• IUPAC Name: [(3R,4S,5R,6R)-5-hydroxy-6-[4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-8-methyl-2-oxochromen-7-yl]oxy-3-methoxy-2,2-dimethyloxan-4-yl] carbamate
• InChI: InChI=1S/C31H36N2O11/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)/t23-,25+,26-,29-/m1/s1
• InChIKey: YJQPYGGHQPGBLI-KGSXXDOSSA-N
• SMILES: CC1=C(C=CC2=C1OC(=O)C(=C2O)NC(=O)C3=CC(=C(C=C3)O)CC=C(C)C)OC4C(C(C(C(O4)(C)C)OC)OC(=O)N)O

Novobiocin (CAS 303-81-1) is an aminocoumarin antibiotic isolated from a number of species of Streptomyces. Novobiocin exhibits broad spectrum Gram +ve activity and was used clinically. Novobiocin is a potent inhibitor of bacterial DNA gyrase and acts as a competitive inhibitor of the ATPase reaction catalysed by GyrB.

Reference

1.Gellert, Martin, et al. "Novobiocin and coumermycin inhibit DNA supercoiling catalyzed by DNA gyrase." Proceedings of the National Academy of Sciences 73.12 (1976): 4474-4478.
2.Burlison, Joseph A., et al. "Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of hsp90." Journal of the American Chemical Society 128.48 (2006): 15529-15536.
3.Mullins, John D., and Thomas J. Macek. "Some pharmaceutical properties of novobiocin." Journal of the American Pharmaceutical Association 49.4 (1960): 245-248.