P-Hydroxypropionic acid

P-Hydroxy acids lose water, especially in the presence of an acid catalyst, to give a,P-unsaturated acids, and frequendy P,y-unsaturated acids. P-Hydroxy acids do not form lactones readily because of the difficulty of four-membered ring formation. The simplest P-lactone, P-propiolactone, can be made from ketene and formaldehyde in the presence of methyl borate but not from P-hydroxypropionic acid. P-Propiolactone [57-57-8] is a usehil intermediate for organic synthesis but caution should be exercised when handling this lactone because it is a known carcinogen. 

These acids are formed sequentially from acrylic acid and water via p-hydroxypropionic acid as intermediate. Yields are dependent on the amount of water present in the reaction mixture. 

An open-chain compound, the lactic acid ester of P-hydroxypropionic acid (VIII in Formula 4.67) can also be formulated from 1-deoxyosone via 1,5-dideoxyosone. Hydration of this P-dicarbonyl compound and subsequent cleavage of the bond between C-2 and C-3 directly yield the lactic acid ester (Formula 4.78). Among the compounds mentioned, acetylformoin is one of the comparatively... 

T., Kawai, K, and Suzuki, T. (1993) P-hydroxypropionic acid production by Byssochlamys sp. grown on acrylic acid. 

Microbial or enzymatic conversion of renewable resources Lactic acid Succinic acid 1.3- Propanediol Itaconic acid 2.3- Butanediol 3-Amino-4-hydroxy- benzoic acid Amino acids Glucose Trehalose Glucaric acid Erythritol P-Hydroxybutyric acid P-Hydroxypropionic acid Itaconic acid Isoprene ... 

This transformation has been used widely to prepare optically active p-hydroxycarboxylic acids. This process takes place in two stages in initial dehydrogenation to the a,p-unsat-urated carboxylic acid and subsequent hydration. These steps utilize the enzymes of the P-oxidation pathway of lipid cataboUsm, and so the P-hydroxy acids produced are generally of the natural S) form. Both saturated carboxylic acids and their a,P unsaturated counterparts have been used as raw materials. For example, P-hydroxypropionic acid (HPA) has been prepared from acrylic acid through a process mediated by Fusarium [17], and Pseduomonas putida has been used to prepare (5)-P-hydroxyisobutyric acid from isobutyric acid [18]. The preparation of C -C (5)-P-hydroxycarboxylic acids from the corresponding tran -a,p-unsaturated carboxylic acids by microbial hydration catalyzed by resting cells of Mucor sp. has also been reported [19] (Scheme 7). 

The use of C. rugosa to produce (/ )-p-hydroxyisobutyric acid from isobutyric acid, although novel, was not yet efficient enough to be adopted on an industrial scale. The conversion never exceeded 50% and the byproduct, p-hydroxypropionic acid, was present at a concentration of about 10% of that of (/ )-p-hydroxyisobutyric acid. It is probable that P-hydroxypropionic acid is produced from (i )-p-hydroxyisobutyric acid via propionic acid by this microorganism, through the valine catabolic pathway. It seemed reasonable. 

There are two pathways for the degradation of nitriles (a) direct formation of carboxylic acids by the activity of a nitrilase, for example, in Bacillus sp. strain OxB-1 and P. syringae B728a (b) hydration to amides followed by hydrolysis, for example, in P. chlororaphis (Oinuma et al. 2003). The monomer acrylonitrile occurs in wastewater from the production of polyacrylonitrile (PAN), and is hydrolyzed by bacteria to acrylate by the combined activity of a nitrilase (hydratase) and an amidase. Acrylate is then degraded by hydration to either lactate or P-hydroxypropionate. The nitrilase or amidase is also capable of hydrolyzing the nitrile group in a number of other nitriles (Robertson et al. 2004) including PAN (Tauber et al. 2000). 

Synonyms AI3-24257 AIDS-6024 Betaprone BPL BRN 0001360 Caswell No. 709 CCRIS 536 EINECS 200-340-1 EPA pesticide chemical code 010901 Hydracrylic acid p iactone 3-Hydroxypropionic acid lactone p Lactone NSC 21626 Oxetan-2-one 2-Oxetanone Propano-lide Propiolactone 1,3-Propiolactone 3-Propiolactone p Propionolactone 3-Propionolactone p Propro-lactone UN 2810. 

Hydroxyphenol, see Hydroquinone p-Hydroxyphenol, see Hydroquinone 4-Hydroxy-3-(l-phenyl-3-oxobutyl)coumarin, see Warfarin 1 -Hydroxypropane, see 1 -Propanol 3 Hydroxypropene, see Allyl alcohol 3 Hydroxypropionic acid lactone, see p-Propiolactone... 

Synonyms-. Hydracrylic acid, 3-lactone 3-hydroxypropionic acid, lactone 3-hydroxypropionic acid, P-lactone propanol ide 3-propanolide propiolactone 3-propiolactone P-propionolactone... 

Nevertheless, malonyl-CoA is a major metabolite. It is an intermediate in fatty acid synthesis (see Fig. 17-12) and is formed in the peroxisomal P oxidation of odd chain-length dicarboxylic acids.703 Excess malonyl-CoA is decarboxylated in peroxisomes, and lack of the decarboxylase enzyme in mammals causes the lethal malonic aciduria.703 Some propionyl-CoA may also be metabolized by this pathway. The modified P oxidation sequence indicated on the left side of Fig. 17-3 is used in green plants and in many microorganisms. 3-Hydroxypropionyl-CoA is hydrolyzed to free P-hydroxypropionate, which is then oxidized to malonic semialdehyde and converted to acetyl-CoA by reactions that have not been completely described. Another possible pathway of propionate metabolism is the direct conversion to pyruvate via a oxidation into lactate, a mechanism that may be employed by some bacteria. Another route to lactate is through addition of water to acrylyl-CoA, the product of step a of Fig. 17-3. Tire water molecule adds in the "wrong way," the OH ion going to the a carbon instead of the P (Eq. 17-8). An enzyme with an active site similar to that of histidine ammonia-lyase (Eq. 14-48) could... 

Benzaldehyde dimethylacetal (200 pi, 1.33 mmol) and a catalytic amount of p-toluenesulfonic acid (37 mg) are added to methyl (2R,3S)-3-(4-nitrobenzenesulfonamido)-3-phenyl-2-hydroxypropionate (315 mg, 0.83 mmol) in toluene 5 ml. The mixture is heated at 100°C under reduced pressure (15 mm mercury) with no condenser. After 1 h the crude reaction mixture is diluted with ethyl acetate and washed with water (2 times). After drying the organic layer over magnesium sulfate the crude material is purified by column chormatography (silica gel eluting with ethyl acetate/cyclohexane, 35/65) to give the (2S,4S,5R)-2,4-diphenyl-3-(4-nitrobenzenesulfonamido)-5-methoxycarbonyl-l,3-oxazolidine, melting point 118°-120°C. 

Suthers, P.F. and Cameron, D.C. 2005. Production of 3-Hydroxypropionic Acid in Recombinant Organisms. United States Patent number 6852517. 

Zhang, D., Hillmyer, M.A. and Tolman, W.B. 2004. A New Synthetic Route to Poly[3-Hydroxypropionic Acid] (P[3-HP]) Ring-Opening Polymerization of 3-HP Macrocyclic Esters. Macromol., 37, 8198-8200. 

Urinary organic acid analysis is useful for differentiating isolated carboxylase deficiencies from the biotin-responsive multiple carboxylase deficiencies. P-Hydroxyisovalerate is the most common urinary metabolite observed in isolated P-methylcrotonyl-CoA carboxylase deficiency, biotinidase deficiency, biotin holo-carboxylase synthetase deficiency, and acquired biotin deficiency. In addition to P-hydroxy-isovalerate, elevated concentrations of urinary lactate, methylcitrate, and P-hydroxypropionate are indicative of multiple carboxylase deficiency. 

Hydroxypropionic acid lactone NSC-21626 Oxetanone Oxetan-2-one 2-Oxetanone Propanlllde Propanoic acid, 3-hydroxy-, p-lactone Propanolide 3-Propanolide P-Propanoic acid lactone p-Propiolactone p-propiolakton p-Propiono-lactone, p-Proprolactone 1,3-Propiolactone 3-Propio-lactone Propiolactona Propiolactone Propiolactone, p- Propiolactonum Propiolattone Propionic acid, 3-hydroxy-, p-lactone Propionolactone. Chemical inter-mediate used as a disinfectant. Liquid mp = -34.4" bp = 162° (dec) df = 1.1460 soluble in H2O (35 g/100 ml) LCso (rat ihl) = 25 ppm/6H. O Neal Jones Feldman Pharm. 

SYNONYMS bpl, hydracrylic acid P-lactone, 3-hydroxy-P-lactone, 3-hydroxypropionic acid lactone, 2-oxetanone, propanolide, 1,3-propiolactone, 3-propiolactone. 

Synonyms BPL Hydracryiic acid p-lactone 3-Hydroxypropionic acid lactone 2-Oxetanone Propanolide... 

CAS 56-45-1 EINECS/ELINCS 200-274-3 Synonyms 2-Amino-3-hydroxypropionic acid L-P-Hydroxyalanine Ser Serine (INCI) (S)-(+)-Serine... 

The biosynthetic pathway for MDP chromophore involves the production of (i) aminosugar previously named madurose (ii) p-hydroxyacid (S)-3-(2-chloro-3-hydro xy-4-methoxyphenyl)-3-hydroxypropionic acid derived from L-a-tyrosine (iii) 6-methylsalicyl-CoA and (iv) enediyne portion and a convergent biosynthetic approach to the final MDP chromophore. 

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