P-Aminoisobutyric acid

RS- P-Aminoisobutyric acid (a-methyl-P-alanine) [10569-72-9] M 103.1, m 176-178 , 178-180 , 181-182 , R -(-)- isomer [144-90-1] m 183 , [a] -21 (c 0.43, HjO), pKes,(,) 3.7, pKEst(2) 10.2. Colorless prisms from hot H O, were powdered and dried in vacuo. The purity is checked by paper chromatography (Whatman 1) using ninhydrin spray to visualise the amino acid Rp values in 95% MeOH and n-PrOH/5N HCOOH (8 2) are 0.36 and 0.50 respectively. [Kupiecki and Coon Biochem Prep 7 20 7960 Pollack J Am Chem Soc 65 1335 7943.] The R-enantiomer, isolated from iris bulbs or human urine was crystd from H2O and sublimed in vacuo [Asen et al. J Biol Chem 234 343 7959]. The RS-hydrochloride was recrystd from EtOH/Et20 m 128-129 , 130° [Bbhme et al. Chem Ber92 1258, 1260, 1261 7959]. 

C2. Calchi-Novati, C., Ceppellini, R., Biancho, I., Silvestroni, E., and Harris, H., p-aminoisobutyric acid excretion in urine. A family study in an Italian population. Ann. Eugenics 18, 335-336 (1954). 

D5. de Groucny, J., and Eldon-Sutton, H., Genetic study of P-aminoisobutyric acid excretion. Am. J. Human Genet. 9, 76-80 (1957). 

Enzymatic synthesis of 3H-labelled P-ureidoisobutyric acid and P-aminoisobutyric acid from pHJthymidine... 

P-aminoisobutyric acid 59.3 pCi, p-ureidoisobutyric acid 18.8 pCi, radiochemical purity > 99% radiochemical purity > 99%... 

Cells have free amino acid concentrations about 10 times those of plasma. The mechanisms maintaining this tenfold P-aminoisobutyric acid is seen. The mechanisms maintaining the gradient are unknown but may involve the membrane enzyme y-glutamyl transferase. 

Some amino acid analogues such as a-[met/zy/- C]methylphenylalanine and a-[ C-methyl]methyltyrosine have been synthesized by alkylations of malonic esters (Gee and Langstrom 1991) as well as a-[met/zy/- C]methyltryptophan (Bourne et al. 1991 Pulak et al. 1996). a-aminoisobutyric acid, labeled in either the carboxylic position (Dunzendorfer et al. 1981) or 2-position (Prenant et al. 1995a), or the 3-position (Oberdorfer et al. 1993 Schmall et al. 1996) and P-aminoisobutyric acid (Alauddin et al. 1997) are other examples. Other... 

Kakimoto, Y., a. Kanazawa, T. Nakajima, and I. Sano Isolation of y-L-glutamyl-L-p-aminoisobutyric acid from bovine brain. Biochem. Biophys. Acta 100, 426 (1965). Kanamori, T., and H. Matsumoto Glutamine synthetase from rice plant roots. Arch. Biochem. Biophys. 125, 404 (1972). 

Morris, C. J., J. F. Thompson, S. Asen, and F. Irreverre The isolation of y-L-glutamyl-p-aminoisobutyric acid from Iris bulbs. J. Biol. Chem. 236, 1181 (1961). 

Begriche, K., Massart, J., and Fromenty, B. (2010) Effects of P-aminoisobutyric acid on leptin production and lipid homeostasis mechanisms and possible relevance for the prevention of obesity. Fundam. Clin. Pharmacol, 24 (3), 269-282. 

Farkas, Walter R., Ali Fischbein, Stephen Solomon, et al. 1987. Elevated Urinary Excretion of P-Aminoisobutyric Acid and Exposure to Inorganic Lead. Archives of Environmental Health 42 96-99. 

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