RifamycinS

RifamycinS Structure
RifamycinS structure
Common Name RifamycinS
CAS Number 13553-79-2 Molecular Weight 695.753
Density 1.3±0.1 g/cm3 Boiling Point 917.4±65.0 °C at 760 mmHg
Molecular Formula C37H45NO12 Melting Point 179-181ºC (dec.)
MSDS N/A Flash Point 508.6±34.3 °C

Polyketide construction via hydrohydroxyalkylation and related alcohol C-H functionalizations: reinventing the chemistry of carbonyl addition.

Nat. Prod. Rep. 31(4) , 504-13, (2014)

Despite the longstanding importance of polyketide natural products in human medicine, nearly all commercial polyketide-based drugs are prepared through fermentation or semi-synthesis. The paucity of manufacturing routes involving de novo chemical synthesis re...

Synthesis and structure-activity relationships of novel substituted 8-amino, 8-thio, and 1,8-pyrazole congeners of antitubercular rifamycin S and rifampin.

Bioorg. Med. Chem. Lett. 21 , 6094-9, (2011)

A series of rifamycin S and rifampin analogues incorporating substituted 8-amino, 8-thio, and 1,8-pyrazole substituents has been synthesized. The compounds were made by activation of the C-8 phenol as a sulfonate ester, followed by displacement with selected ...

Direct generation of acyclic polypropionate stereopolyads via double diastereo- and enantioselective iridium-catalyzed crotylation of 1,3-diols: beyond stepwise carbonyl addition in polyketide construction.

J. Am. Chem. Soc. 133(32) , 12795-800, (2011)

Under the conditions of transfer hydrogenation employing the cyclometalated iridium catalyst (R)-I derived from [Ir(cod)Cl](2), allyl acetate, 4-cyano-3-nitrobenzoic acid, and the chiral phosphine ligand (R)-SEGPHOS, α-methylallyl acetate engages 1,3-propaned...

Detoxification of toxins by bacillithiol in Staphylococcus aureus.

Microbiology 158(Pt 4) , 1117-26, (2012)

Bacillithiol (BSH), an α-anomeric glycoside of l-cysteinyl-d-glucosaminyl-l-malate, is a major low-molecular-mass thiol found in bacteria such as Bacillus sp., Staphylococcus aureus and Deinococcus radiodurans. Like other low-molecular-mass thiols such as glu...

Solid state cultivation of Curvularia lunata for transformation of rifamycin B to S.

Indian J. Exp. Biol. 40(8) , 930-3, (2002)

Biotransformation of rifamycin B to rifamycin S using two strains of C. lunata namely NCIM 716 and NMU grown on various solid substrates viz., grass, paper, jowar/wheat straw, bran and bagasse was studied. Almost complete biotransformation efficiency of rifam...

Studies on rifamycin oxidase immobilized on kappa-carrageenan gel.

Biomater. Artif. Cells Immobilization Biotechnol. 21(5) , 665-74, (1993)

Rifamycin oxidase from Curvularia lunata var. aeria was immobilized on kappa-carrageenan gel where the enzyme showed excellent catalyzing activity and operational stability. Factors affecting the activity of immobilized enzyme preparation such as pH and tempe...

Transformation of rifamycin S into rifamycins B and L. A revision of the current biosynthetic hypothesis.

J. Antibiot. 35(1) , 74-80, (1982)

The transformation of rifamycin S into rifamycins B and L was reinvestigated in order to establish more detailed pathways. Our results exclude rifamycin O as a common progenitor in the biosyntheses of rifamycins B and L. Rifamycins B and L are formed from rif...

Oxygen Enhancement of bactericidal activity of rifamycin SV on Escherichia coli and aerobic oxidation of rifamycin SV to rifamycin S catalyzed by manganous ions: the role of superoxide.

J. Biochem. 91(1) , 381-95, (1982)

Oxygen enhanced the bactericidal activity of rifamycin SV to Escherichia coli K12. Anaerobically grown cells, which had a low level of superoxide dismutase, were more susceptible to the bactericidal activity than aerobically grown cells, which contained a hig...

Molecular structure and conformation of rifamycin S, a potent inhibitor of DNA-dependent RNA polymerase.

J. Antibiot. 45(3) , 428-31, (1992)

NMR spectroscopic analysis of new spiro-piperidylrifamycins.

Magn. Reson. Chem. 43(4) , 269-82, (2005)

New spiro-piperidylrifamycin derivatives are presented. These compounds were synthesized from the reaction of 3-amino-4-iminorifamycin S and enantiomerically pure 4-piperidones, which generate diasteroisomeric rifabutin analogues with a new stereocentre at th...