18951-35-4Relevant academic research and scientific papers
Corynomycolic acid-containing glycolipids signal through the pattern recognition receptor Mincle
Van Der Peet,Gunawan, Christian,Torigoe, Shota,Yamasaki, Sho,Williams, Spencer J.
, p. 5100 - 5103 (2015)
An enantioselective synthesis of (+)-corynomycolic acid, and its elaboration to esters of trehalose, glucose and glycerol, is described. Trehalose dicorynomycolate and trehalose monocorynomycolate activate human and mouse Mincle as effectively as trehalose dicorynomycolate (cord factor). Glucose monomycolate is revealed to be a potent activator of both mouse and human Mincle. Glycerol monocorynomycolate signals through human Mincle, with the activity predominantly residing in the 2′S-isomer.
Adjuvant properties of a simplified C32 monomycolyl glycerol analogue
Bhowruth, Veemal,Minnikin, David E.,Agger, Else Marie,Andersen, Peter,Bramwell, Vincent W.,Perrie, Yvonne,Besra, Gurdyal S.
scheme or table, p. 2029 - 2032 (2009/12/03)
A simplified C32 monomycolyl glycerol (MMG) analogue demonstrated enhanced immunostimulatory activity in a dioctadecyl ammonium bromide (DDA)/Ag85B-ESAT-6 formulation. Elevated levels of IFN-γ and IL-6 were produced in spleen cells from mice immunised with a C32 MMG analogue comparable activity to the potent Th1 adjuvant, trehalose 6,6′-di-behenate (TDB).
Enantioselective Hydrogenation of β-Keto Esters using Chiral Diphosphine-Ruthenium Complexes: Optimization for Academic and Industrial Purposes and Synthetic Applications
Ratovelomanana-Vidal,Girard,Touati,Tranchier,Ben Hassine,Genet
, p. 261 - 274 (2007/10/03)
Enantioselective hydrogenation using chiral complexes between atropisomeric diphosphines and ruthenium is a powerful tool for producing chiral compounds. Using a simple and straightforward in situ catalyst preparation, the conditions were optimized using molecular hydrogen for both academic and industrial purposes. This led to the best conditions and the lowest catalytic ratio required for the pressure used. Hydrogenation of various β-keto esters was efficiently performed at atmospheric and higher pressures, leading to the use of very low catalyst-substrate ratios up to 1/20,000. Asymmetric hydrogenations were used in key-steps towards the total synthesis of corynomycolic acid, Duloxetine and Fluoxetine.
An improved synthesis of trehalose 6-mono- and 6,6'-di-corynomycolates and related esters
Datta, Arun K.,Takayama, Kuni,Nashed, Mina A.,Anderson, Laurens
, p. 95 - 109 (2007/10/02)
A simplified synthesis of 6-mono- and 6,6'-di-corynomycolate esters of α,α-trehalose, and related compounds, was achieved by coupling the (hydroxyl-protected) acids to the partially trimethylsilylated sugar in the presence of dicyclohexylcarbodiimide and 4-dimethylaminopyridine.As acid reactants, (2-RS,3-RS)-3-hydroxy-2-tetradecyloctadecanoic acid (DL-corynomycolic acid) and its 2RS, 3SR diastereomer were prepared from methyl palmitate by sequential Claisen condensation, reduction, chromatographic separation, and saponification.Reaction with tert-butylchlorodimethylsilane (imidazole) gave the disubstituted ether-esters, which were converted into the required 3-tert-butyldimethylsilyl ethers by partial hydrolysis. 6-Linked monocorynomycolate was obtained in excellent yield (78percent) from the reaction of the RS,SR acid with the known heptakis-O-(trimethylsilyl)trehalose, and in good yield from equimolar portions of RS,RS acid and hexakis-O-(trimethylsilyl)trehalose.An excess (2.5-molar portions) of the RS,RS acid gave the 6,6'-diester (69percent).The mono- and di-palmitate were similarly obtained from (Me3Si)6-trehalose.The mono (RS,RS)-(Me3Si)6-trehalose coupling product was partially resolved on a silica gel column into its RR and SS diastereomers, the former corresponding to the naturally occurring trehalose monocorynomycolate.All coupling products were deprotected to free trehalose esters by treatment first with K2CO3 in methanol, then tetrabutylammonium fluoride-trifluoracetic acid in oxolane.
Trehalose derivatives
-
, (2008/06/13)
A trehalose derivative of the formula: STR1 wherein one, two, three or four of R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from the group consisting o
A General Method for the Synthesis of Both Enantiomers of Optically Pure β-Hydroxy Esters from (S)-(p-Chlorophenylsulfinyl)acetone Easily Obtainable by Kinetic Resolution with Bakers' Yeast
Fujitsawa, Tamotsu,Fujimura, Atsushi,Sato, Toshio
, p. 1273 - 1280 (2007/10/02)
Both enantiomers of various optically pure (R)- and (S)-β-hydroxy esters were generally synthesized from (S)-(p-chlorophenylsulfinyl)acetone obtained by kinetic resolution with bakers' yeast, followed by γ-alkylation, diastereoselective reduction, subsequent introduction of ester group and reductive elimination of the sulfinyl group.The key step of the diastereoselective reduction of (S)-β-keto sulfoxides was performed with diisobutylaluminum hydride to give (R)C-(S)S-β-hydroxy sulfoxides or after complexation with zinc chloride followed by addition of diisobutylaluminum hydride to give (S)C-(S)S-β-hydroxy sulfoxides which were easily separated in an optically pure form by easy crystallization or separation by silica-gel chromatography due to the p-chlorophenyl moiety in the β-hydroxy sulfoxides.The utility of the present method could be successfully demonstrated in the synthesis of both (+)- and (-)-corynomycolic acids from optically pure methyl esters of (R)- and (S)-3-hydroxyoctadecanoic acid by alkylation with tetradecyl iodide at α-position and hydrolysis.
Asymmetric Reduction of 3-Oxo-octadecanoic Acid with Fermenting Baker's Yeast. An Easy Synthesis of Optically Pure (+)-(2R,3R)-Corynomycolic Acid
Utaka, Masanori,Higashi, Hiroshi,Takeda, Akira
, p. 1368 - 1369 (2007/10/02)
Optically pure (+)-corynomycolic acid has been synthesized from methyl acetoacetate by a route including asymmetric reduction of 3-oxo-octadecanoic acid with baker's yeast as a key step.
DIASTEREO- AND ENANTIOSELECTIVE PREPARATION OF β-ALKYLHOMOALLYLIC ALCOHOLS SYNTHESIS OF SERRICORNIN AND CORYNOMYCOLIC ACID
Kobayashi, Yuichi,Kitano, Yasunori,Takeda, Yoshiyuki,Sato, Fumie
, p. 2937 - 2944 (2007/10/02)
A new and efficient method for the preparation of four possible stereoisomers of β-alkylhomoallylic alcohols 1 has been developed which is based on the diastereoselective addition of nucleophiles to optically active α-alkyl-β-trimethylsilyl-β,γ-unsaturate
REGIO- AND DIASTEREOSELECTIVE ALDOL REACTION OF 1,2-CYCLOHEXANEDIONE DIANIONS WITH ALDEHYDES
Utaka, Masanori,Hojo, Makoto,Takeda, Akira
, p. 1471 - 1474 (2007/10/02)
The aldol reaction of 1,2-cyclohexanedione dianions with various aldehydes afforded threo and erythro aldols in a ratio of 82:18->99:1 in 60-85percent yields.A diastereoselective synthesis of racemic corynomycolic acid was achieved by using the reaction.
