Rifamycin, 4-O-(carboxymethyl)-

Base Information

• Chemical Name: Rifamycin, 4-O-(carboxymethyl)-
• CAS No.: 13929-35-6
• Molecular Formula: C39H49NO14
• Molecular Weight: 755.816
• European Community (EC) Number: 237-697-8
• NSC Number: 145604
• Mol file: 13929-35-6.mol

Synonyms:Nacimycin;Rifomycin B;Rifamycin, 4-O-(carboxymethyl)-;NSC-145604;NCI 145-604;NSC145604;Acetic acid,2-dihydro-5,6,17,19,21-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-9-yl)-oxy]-, 21-acetate;Acetic acid,2-dihydro-5,6,17,19,21-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-9-yl)oxy]-, 21-acetate;WLN: T C6 B65-24- A D E 2BC G& AV LO NO F&VM DU OU B&U D&U MHT&TTJ DO1VQ GQ IQ J1 M1 QO1 R1 SOV1 T1

Chemical Property of Rifamycin, 4-O-(carboxymethyl)-

Chemical Property:

• Vapor Pressure: 1.78E-35mmHg at 25°C
• Melting Point: 300° (dec 160-164°)
• Refractive Index: 1.5350 (estimate)
• Boiling Point: 907.1°Cat760mmHg
• PKA: 2.69±0.10(Predicted)
• Flash Point: 502.4°C
• PSA: 227.61000
• Density: 1.37g/cm³
• LogP: 4.64990
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 6
• Exact Mass: 755.31530524
• Heavy Atom Count: 54
• Complexity: 1460

Purity/Quality:

99% ^*data from raw suppliers

Rifamycin B ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C=CC=C(C(=O)NC2=CC(=C3C(=C2O)C(=C(C4=C3C(=O)C(O4)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C)O)OCC(=O)O)C
• Isomeric SMILES: CC1/C=C\C=C(/C(=O)NC2=CC(=C3C(=C2O)C(=C(C4=C3C(=O)C(O4)(O/C=C\C(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C)O)OCC(=O)O)\C
• Uses: A Rifamycin (R508200) derivative as antibacterial agent. Rifamycin B (Rifaximin EP Impurity B) is a Rifamycin (R508200) derivative as antibacterial agent.

Technology Process of Rifamycin, 4-O-(carboxymethyl)-

There total 5 articles about Rifamycin, 4-O-(carboxymethyl)- 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: 0.4%

D-Glucose (2280-44-6) → 5-deoxy-5-amino-shikimic acid (178948-66-8) + Rifamycin B (13929-35-6)

Guidance literature:

With oxygen; In various solvent(s); at 28 ℃; for 288h; Microbiological reaction;

DOI:10.1021/ol049666e

Reference yield:

rifamycin L → Rifamycin B (13929-35-6)

Guidance literature:

With cytochrome P₄₅₀ enzyme Rif₁₆; ferredoxin reductasese FdR; ferredoxin seFdx; NADPH; In aq. buffer; at 28 ℃; for 4h; Reagent/catalyst; Enzymatic reaction;

DOI:10.1038/s41467-018-04772-x

Reference yield:

rifamycin S (62623-68-1,76188-88-0,81203-58-9,101978-28-3,13553-79-2) → Rifamycin B (13929-35-6)

Guidance literature:

Multi-step reaction with 2 steps

1: transketolase Rif₁₅; cytochrome P₄₅₀ enzyme Rif₁₆; thiamine pyrophosphate; magnesium chloride / aq. buffer / 4 h / 28 °C / pH 7.4 / Enzymatic reaction

2: ferredoxin seFdx; ferredoxin reductasese FdR; NADPH; cytochrome P₄₅₀ enzyme Rif₁₆ / aq. buffer / 4 h / 28 °C / Enzymatic reaction

With cytochrome P₄₅₀ enzyme Rif₁₆; ferredoxin reductasese FdR; ferredoxin seFdx; transketolase Rif₁₅; thiamine pyrophosphate; NADPH; magnesium chloride; In aq. buffer;

DOI:10.1038/s41467-018-04772-x

upstream raw materials:

D-Glucose

rifamycin S

rifamycin SV

Downstream raw materials:

Rifamycin-B-pyrrolidid

Rifamycin-B-(2,6-dimethyl-morpholid)

Rifamycin-B-methylmorpholinoamid

Rifamycin-B-

Refernces

• 1、 Guo, Jiantao,Frost. "Synthesis of aminoshikimic acid". . p. 1585 - 1588. Retrieved 2007/10/03.