Novobiocin

Base Information

• Chemical Name: Novobiocin
• CAS No.: 303-81-1
• Molecular Formula: C₃₁H₃₆N₂O₁₁
• Molecular Weight: 612.634
• Hs Code.: 2941906000
• Mol file: 303-81-1.mol

Synonyms:Benzamide,N-[7-[[3-O-(aminocarbonyl)-6-deoxy-5-C-methyl-4-O-methyl-a-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl]-4-hydroxy-3-(3-methyl-2-butenyl)-(9CI); Coumarin, 7-[4-(carbamoyloxy)tetrahydro-3-hydroxy-5-methoxy-6,6-dimethylpyran-2-yloxy]-4-hydroxy-3-[4-hydroxy-3-(3-methyl-2-butenyl)benzamido]-8-methyl-(6CI); Novobiocin (8CI); Albamix; Albamycin; Antibiotic PA-93; Cardelmycin;Cathocin; Cathomycin; Crystallinic acid; Inamycin; Novo-R; PA 93; Robiocina; Sirbiocina;Spheromycin; Stilbiocina; Streptonivicin; U 6391

Chemical Property of Novobiocin

Chemical Property:

• Melting Point: 170-172 °C
• Refractive Index: 1.5800 (estimate)
• Boiling Point: 848.2°Cat760mmHg
• PKA: pKa1 4.3; pKa2 9.1(at 25℃)
• Flash Point: 466.8°C
• PSA: 200.01000
• Density: 1.42g/cm³
• LogP: 4.40040
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Novobiocin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): May have damaging side effects.
• Hazard Codes: May have damaging side effects.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• General Description: Novobiocin is an antibiotic that targets bacterial DNA gyrase by inhibiting the ATPase activity of the gyrase B subunit, effectively blocking DNA replication. It has been used clinically against Gram-positive bacteria, though its utility is limited by resistance mechanisms, including efflux pumps. Recent research highlights its role in studying bacterial efflux systems, where it serves as a substrate for efflux pumps like AcrAB-TolC in *Escherichia coli*. Additionally, novobiocin's activity can be potentiated by efflux pump inhibitors, such as modified cinnamoyl amides, which bind to efflux components like AcrA. However, cytotoxicity and resistance remain challenges, prompting investigations into structural analogs and combination therapies to overcome these limitations.

Technology Process of Novobiocin

There total 4 articles about Novobiocin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.3%

sodium novobiocin (1476-53-5,6990-02-9,18656-99-0) → novobiocin (303-81-1,107781-69-1)

Guidance literature:

With hydrogenchloride; In water;

DOI:10.1016/j.bmc.2013.06.042

Reference yield: 70.0%

→ novobiocin (303-81-1,107781-69-1)

Guidance literature:

Reference yield: 58.0%

novobiocin (1445875-24-0) → novobiocin (303-81-1,107781-69-1)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; acetonitrile; at 20 ℃; for 12h; pH=7.5;

DOI:10.1021/jo4010298

upstream raw materials:

carbamoyl phosphate

novobiocin

sodium novobiocin

Downstream raw materials:

coumermycin A1

5-methyl-1H-pyrrole-2-carboxylic acid 6-(4-benzhydryloxy-8-methyl-2-oxo-2H-chromen-7-yloxy)-5-hydroxy-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester

C₃₆H₄₅N₃O₁₁

C₄₀H₄₈N₆O₁₁

Refernces

Alternative and expedient asymmetric syntheses of L-(+)-Noviose

10.1021/ol702655c

The study focused on the asymmetric synthesis of L-(+)-Noviose, a sugar component of the antibiotics novobiocin and coumarin. The goal of the study was to develop alternative and rapid methods to synthesize L-(+)-Noviose from readily available non-carbohydrate starting materials while taking advantage of stoichiometric and asymmetric processes. The researchers achieved this goal through two independent methods, one involving six steps with an overall yield of 27% and the other involving nine steps with an overall yield of 20%. A variety of chemicals were used in the synthesis, including 2,2-dimethyl-1,3-cyclopentanedione, (S)-B-Me-oxaborane ((S)-B-Me-CBS), BH3 N,N-dimethylbenzene complex (DEANB), methyl ethers, Sc(OTf)3, Saegusa oxidation, Pd(OAc)2, trimethylsilyl ketene intermediates, ene palladium, NaH, Grubbs second generation catalyst, DIBALH, water, and other chemicals for non-catalyzed xylene reactions. The study conclusions highlight the successful development of two efficient synthetic routes to L-(+)-Noviose, suitable for the synthesis of unnatural analogs, without the need for protecting groups, and utilizing commercially available reagents such as Corey's CBS and Brown's reagent.

Mechanistic Duality of Bacterial Efflux Substrates and Inhibitors: Example of Simple Substituted Cinnamoyl and Naphthyl Amides

10.1021/acsinfecdis.1c00100

This research endeavored to develop novel small-molecule therapeutics targeting multidrug efflux pumps, which are a significant factor in antibiotic resistance among Gram-negative bacteria. The team focused on modifying the cinnamoyl group of a diaminoquinoline acrylamide, NSC-33353, known to inhibit the AcrAB?TolC efflux pump in Escherichia coli. They synthesized a series of cinnamoyl- and naphthyl-derived amides of the 4,6-diamino-2-methylquinoline scaffold. The cinnamoyl analogs showed strong binding to AcrA, potentiated the activities of antibiotics novobiocin and erythromycin, and inhibited efflux. However, they also demonstrated cytotoxicity. In contrast, naphthyl analogs, which had lower cytotoxicity, did not bind to AcrA but potentiated novobiocin, suggesting a shift in their mechanism of action possibly due to changes in their interaction with AcrB. The study concluded that chemical modifications can significantly alter the activity and mechanism of efflux pump inhibitors, providing valuable insights for developing new therapeutics to combat antibiotic resistance.