Aminopropanoic acid

Aminopropanoic acid known as 3 alanine It IS a p amino acid that makes up one of the stmctural units of coenzyme A... 

B. 3-Isocyanatopropanoyl chloride. A 500-ml., two-necked flask is equipped with a thermometer and a reflux condenser protected at its top by a calcium chloride tube. A Teflon-coated magnetic stirring bar, 250 ml. of anhydrous dioxane (Note 12), 12.6 g. (0.1 mole) of finely pulverized 3-aminopropanoic acid hydrochloride (Note 13), and 23.8 g. (14.4ml., 0.12mole) of trichloromethyl chloroformate (Note 14) are placed in the flask in the order specified. The mixture is stirred and heated at 55-60°. After ca. 5 hours, the solid has completely dissolved, leaving a clear solution. The heating is discontinued after a total of 7 hours (Note 15), and the solvent is removed under reduced pressure. The residual oil is distilled rapidly under reduced pressure and a distillate amounting to 11.2-12.4 g. (84-93%) is collected at 75-85° (20 mm.) (Note 16). Redistillation affords 10.5-11.8 g. (79-88%) of 3-isocyanatopropanoyl chloride as a colorless liquid, b.p. 92-94° (25 mm.) (Note 17). 

Aminopropanoic acid O-alanine) is available from Aldrich Chemical Company, Inc., and from the Nutritional Biochemical Division, TCN Products. The hydrochloride salt is prepared in the following manner. A solution of 89 g. (1.0 mole) of 3-aminopropanoic acid in 200 ml. of water is acidified by addition of 100 ml. (1.2 mole) of concentrated hydrochloric acid and then concentrated to a white solid with a rotary evaporator. The solid is pulverized to a fine powder and dried at 60° under reduced pressure. The yield of 3-aminopropanoic acid hydrochloride amounts to 113-125 g. (90-100%). 

Trichloromethyl chloroformate has proven effective in the preparation of N-carboxy-a-amino acid anhydrides from amino acids, and various compounds having isocyanate, acid chloride, and chloroformate groups.For example, trichloromethyl chloroformate may be used instead of phosgene in the preparation of 2-tert-butoxycarbonyloxyimino-2-phenylacetonitrile. The use of this reagent is illustrated here by the synthesis of 3-isocyanato-propanoyl chloride from 3-aminopropanoic acid hydrochloride. 

Dioxane p-Dioxane (8) 1,4-Dioxane (9) (123-91-1) 3-Aminopropanoic acid hydrochloride /3-Alanine, hydrochloride (8, 9) (6057-90-5)... 

Whereas /3-alanine (3-aminopropanoic acid, homoglycine) is found in nature, many other /3-amino acids are not. Indeed, the development of /3-peptides owes much to the pioneering work of Seebach and co-workers [221] [222],... 

Amino acids capable of forming lactams give low yields of (trifluoromethyl)amines. Thus, 4-aminobutanoic acid gives 4.4,4-trifluorobutylamine (14b) in only 7% yield, while 3,3,3-tri-fluoropropylaminc (14a) is formed from 3-aminopropanoic acid in 41 % yield.113... 

The most abundant amino acids are those that are protein constituents and these are always a-amino acids. However, there are many other amino acids that occur naturally in living systems that are not constituents of proteins, and are not a-amino acids. Many of these are rare, but others are common and play important roles in cellular metabolism. For example, 3-aminopropanoic acid is a precursor in the biosynthesis of the vitamin, pantothenic acid,2... 

IUPAC name 3-aminopropanoic acid lactam common name /3-propiolactam... 

The final step of the overall conversion of (S)-asparagine to 2-alkyl-3-aminopropanoic acid, the hydrolysis of heterocycles 5-8, was achieved by heating with 6 N HCl in a sealed tube at 90-100 °C. The free amino acids 9-12 were purified by chromatography on an ion-exchange column (eq 7, Table 2). 

P-alanine (3-aminopropanoic acid) is an amino acid widely distributed in plants, including algae, fungi and many higher plants. It is a residue present in pantothenic acid (a... 

R. J. Abraham, P. Loftus, and W. A. Thomas, Rotational isomerism-XXI. The conformation of 2-amino-3-fluoropropanoic acid (2AFP) and 2-fluoro-3-aminopropanoic acid (3-AFP) as the zwitter-ion, cation, and anion, an NMR and MO study, Tetrahedron, 33 (1977) 1227-1234. 

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