Hydroxymethyl glutarate

Three compounds acetoacetate, P-hydroxybutyrate, and acetone, are known as ketone bodies. They are suboxidized metabolic intermediates, chiefly those of fatty acids and of the carbon skeletons of the so-called ketogenic amino acids (leucine, isoleucine, lysine, phenylalanine, tyrosine, and tryptophan). The ketone body production, or ketogenesis, is effected in the hepatic mitochondria (in other tissues, ketogenesis is inoperative). Two pathways are possible for ketogenesis. The more active of the two is the hydroxymethyl glutarate cycle which is named after the key intermediate involved in this cycle. The other one is the deacylase cycle. In activity, this cycle is inferior to the former one. Acetyl-CoA is the starting compound for the biosynthesis of ketone bodies. 

Hydroxymethyl Glutarate Cycle. At the first step of this cycle, condensation of two acetyl-CoA molecules takes place, with the participation of acetyl CoA acetyltransferase ... 

Acetyl-CoA is again used at the first step and closes thereby the whole process into a cycle. Acetoacetate, as a representative of the ketone body family, is the end product of the hydroxymethyl- glutarate cycle. 

With diethyl malonate. Two different products are obtainable in moderate yield by reaction of malonic ester with formalin. With a 1 2 ratio of aldehyde to ester and diethylamine as catalyst, the product is the tetraester (1), an intermediate in one synthesis of glutaric acid. With a 2 1 ratio and potassium bicarbonate as catalyst, the product is the crystalline solid diethyl bis(hydroxymethyl)malonate (2). ... 

BS3, bis(sulfosuccinimidyl) suberate DSG, disuccinimidyl glutarate DSS, disuccinimidyl suberate GTA, glutaraldehyde HMDI, hexamelhylene diisocyanale PQQ, pyrroloquinoline quinine THPP, tris(hydroxymethyl)phosphino-propionic acid TSAT, Iris-succinimidyl aminolriacetrate. 

TMEDA. See 1,3-Diaminopropane N,N,N, N -Tetramethylethylenediamine TMG. See Tetramethyl guanidine TMG acid. See 3,3-Tetramethylene glutaric acid TMI. See p-Tolyl isocyanate m-TMI. Seem-Tolyl isocyanate 3-[(Prop-1-en-2-yl) phenyl] prop-2-yl isocyanate o-TMI. See o-Tolyl isocyanate p-TMI. See p-Tolyl isocyanate TMi (Meta). See 3-[(Prop-1-en-2-yl) phenyl] prop-2-yl isocyanate TML. See Tetramethyl lead TMOS. See Tetramethoxysilane TMP. See Trimethylolpropane 2,3,6-TMP. See 2,3,6-Trimethylphenol 2,4,-TMP. See Isooctane TMPC. See Tetrakis (hydroxymethyl) phosphonium chloride... 

Potassium dimethyidithiocarbamate biocide, swimming pools 1 -Bromo-3-chloro-5,5-dimethyl hydantoin biocide, textile dyeing Cetalkonium chloride biocide, textile processing solutions 2[(-Hydroxymethyl) amino] ethanol biocide, textile spinning Sodium o-phenylphenate biocide, textile treatments Octadecyidimethyl [3-(trimethoxysilyl) propyl] ammonium chloride biocide, textiles Tributyltin oxide biocide, timber Sodium o-phenylphenate biocide, timber preservation Methylenebis (thiocyanate) biocide, veterinary fields Succinaldehyde biocide, veterinary preps. Tetramethylolacetylene diurea biocide, vinyl acetate latex emulsions Sodium pyrithione biocide, water cooling towers Glutaral... 

Materials. Terephthaldicarboxaldehyde (Aldrich), diethyl bis(hydroxymethyl) malonate (Aldrich), p-toluenesulfonic acid (Aldrich), potassium hydroxide (85 wt%, Fisher), pyridine (Fisher), glutaric dialdehyde (50wt% aqueous solution, Aldrich), ethylene glycol divinyl ether (Aldrich), ethyl glycolate (Aldrich), isophthalic dicarboxaldehyde (Lancaster), propionaldehyde (Eastman Chemical), isovaleraldehyde (Aldrich), 2-ethyl-2-oxazoline (Acros), ammonia (7M in methanol, Acros), l-methoxy-4-(methylthio)benzene (Aldrich), silver... 

Fig. 11.2 Total ion current chromatogram (Varian MAT 44 GC-MS) of organic acids extracted using ethyl acetate and diethyl ether from the urine of a patient with propionic acidaemia and separated as their trimethylsilyl derivatives on a 25 m SE-54 WCOT capillary column using temperature programming from 70°C to 220°C at 4 C min Peak identifications are 1, lactate 2, 3-hydroxypropionate 3, 3-hydroxybutyrate 4, 2-methyl-3-hydroxybutyrate 5, 3-hydroxyisovalerate 6, 3-hydroxy- -valerate 7, aceto-acetate 8 and 9, 2-methyl-3-hydroxyvalerate 10, 3-oxovalerate 11, 2-methyl-3-oxo-valerate (isomer 1) 12,2-methylacetoacetate 13,2-methyl-3-oxovalerate (isomer 2) 14 propionylglycine 15, glutarate 16, adipate 17, 5-hydroxymethyl-2-furoate 18, 2-hydroxyglutarate 19,3-hydroxy-3-methylglutarate 20,4-hydroxyphenylacetate 21 and 22, methylcitrate 23,4-hydroxyphenyl-lactate 24, palmitate. (Redrawn with modifications from Truscott et al., 1979)...

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