73684-69-2

Basic information

• Product Name: miporamicin
• Synonyms: miporamicin;A-11725II;Antibiotic A-11725II;Antibiotic AR-5-2;AR-5-2;Mycinamicin II
• CAS NO: 73684-69-2
• Molecular Formula: C₃₇H₆₁NO₁₃
• Molecular Weight: 727.883
• Mol File: 73684-69-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 104°C
• Boiling Point: 710.88°C (rough estimate)
• Flash Point: 463.7°C
• Appearance: /
• Density: 1.1734 (rough estimate)
• Vapor Pressure: 4.81E-33mmHg at 25°C
• Refractive Index: 1.6630 (estimate)
• PKA: 11.98±0.70(Predicted)
• CAS DataBase Reference: miporamicin(CAS DataBase Reference)
• NIST Chemistry Reference: miporamicin(73684-69-2)
• EPA Substance Registry System: miporamicin(73684-69-2)

Safety Data

• Hazardous Substances Data: 73684-69-2(Hazardous Substances Data)

Usage

General Description

Miporamicin is a veterinary antibiotic used in farming animals, particularly in the treatment of respiratory infections in cattle and pigs. It belongs to the class of drugs known as aminoglycosides, which work by interfering with bacterial protein synthesis. Miporamicin is effective against a variety of Gram-positive and Gram-negative bacteria, including several strains that are resistant to other antibiotics. It is administered via injection and has a low level of toxicity, making it a relatively safe and effective treatment option for a range of bacterial infections in livestock. However, it is important to use miporamicin judiciously to prevent the development of antibiotic resistance in agricultural settings.

InChI:InChI=1/C37H61NO13/c1-11-27-37(43,18-46-36-33(45-10)32(44-9)29(41)23(6)48-36)34-26(49-34)14-13-25(39)20(3)16-21(4)31(19(2)12-15-28(40)50-27)51-35-30(42)24(38(7)8)17-22(5)47-35/h12-15,19-24,26-27,29-36,41-43H,11,16-18H2,1-10H3/b14-13+,15-12+/t19-,20+,21-,22+,23+,24-,26-,27+,29+,30+,31+,32+,33+,34+,35-,36+,37-/m0/s1

Synthetic route

mycinamicin II 3'-N-oxide (122825-79-0) → mycinamicin II (73684-69-2)

Conditions	Yield
With triphenylphosphine In dichloromethane at 55℃; for 67h;	56%

mycinamicin-IV → C36H59NO11 + mycinamicin-I + mycinamicin-III (73684-71-6) + mycinamicin V (73684-72-7) + mycinamicin II (73684-69-2)

Conditions	Yield
With multifunctional biosynthetic P450 monooxygenase; rhodococcus reductase domain; NADPH In aq. buffer at 28℃; for 2h; pH=7.3; Kinetics; Reagent/catalyst; Enzymatic reaction;	A 18.5% B n/a C n/a D n/a E n/a

mycinamicin V (73684-72-7) → mycinamicin II (73684-69-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 39 percent / MCPBA, disodium hydrogen phosphate / CH2Cl2 / 23 h / 60 °C 2: 56 percent / triphenylphosphine / CH2Cl2 / 67 h / 55 °C View Scheme

Upstream product

• 122825-79-0 mycinamicin II 3'-N-oxide 
• 73684-72-7 mycinamicin V 

Relevant articles and documents

New reactions and products resulting from alternative interactions between the P450 enzyme and redox partners

Cytochrome P450 enzymes are capable of catalyzing a great variety of synthetically useful reactions such as selective C-H functionalization. Surrogate redox partners are widely used for reconstitution of P450 activity based on the assumption that the choice of these auxiliary proteins or their mode of action does not affect the type and selectivity of reactions catalyzed by P450s. Herein, we present an exceptional example to challenge this postulate. MycG, a multifunctional biosynthetic P450 monooxygenase responsible for hydroxylation and epoxidation of 16-membered ring macrolide mycinamicins, is shown to catalyze the unnatural N-demethylation(s) of a range of mycinamicin substrates when partnered with the free Rhodococcus reductase domain RhFRED or the engineered Rhodococcus-spinach hybrid reductase RhFRED-Fdx. By contrast, MycG fused with the RhFRED or RhFRED-Fdx reductase domain mediates only physiological oxidations. This finding highlights the larger potential role of variant redox partner protein-protein interactions in modulating the catalytic activity of P450 enzymes.