Amino a phenylpropionic Acid

Aminopeptidase, Leucine (Aspergillus nigerwea., Aspergillus oryzae var., and other microbial species), (S3)19 DL-a-Amino-(3-phenylpropionic Acid, 292 L-a-Amino-P-phenylpropionic Acid, 292 DL-2-Aminopropanoic Acid, 18 L-2-Aminopropanoic Acid, 18 L-a-Aminosuccinamic Acid, 35 DL-Aminosuccinic Acid, 36, (S3)7 L-Aminosuccinic Acid, 37, (S2)l, (S3)7 Ammonia-Ammonium Chloride Buffer TS, 850... 

Phenylalanine (a-amino-/3-phenylpropionic acid) cannot be formed in the animal organism because of its aromatic ring. It is closely related to tyrosine which belongs to Group II with its phenolic —OH group. 

AMINOPHENYL)-l-PROPANONE see AMCOOO a-AMINO-P-PHENYLPROPIONIC ACID see PEC750 dl-oc-AMINO-P-PHENYLPROPIONIC ACID see PEC500 9-(4 -AMINOPHENYL)-9H-PYRIDO(3,4-B)INDOLEsee ALX120... 

In this chapter, the discussion will concentrate on two inhibitors with a reasonable claim to selective action on enz3ones related to the shikimate pathway glyphosate, which inhibits 5-enolpyruvylshikimate 3-phosphate (EPSP) synthase and L-a-aminooxy-3 phenylpropionic acid (L-AOPP), an inhibitor of phenylalanine ammonia-lyase (PAL) (Fig. 2). In addition to introducing a novel inhibitor of PAL, (R)-(l-amino-2-phenylethyl)phosphonic acid (APEP), previous and current efforts to design inhibitors of other shikimate pathway enzymes will be described. The treatment presented here will show that the deductions and predictions made on the basis of the abstract scheme in Figure 1 can be, and have been, tested on the basis of the real pathway presented in Figure 2. 

Treatment of 3-acylaminoperhydropyrido[2,l- >][1,3]thiazine-6-carboxy-late (109) with iodotrimethylsilane gave a 3-amino derivative (110). The amino group was acylated with (5)-2-(acetylthio)-3-phenylpropionic acid in the presence of benzotriazol-l-yloxitris(dimethylamino)phosphonium hexafluorophosphate and triethylamine in dichloromethane, and the product (111) was hydrolyzed to 112 (94EUP629627 96USP5508272). 

Amino-2-phenylindenone, 38-39 N-(2-Aminophenyl)piperidine, 826 a-Amino-a-phenylpropionic acid, 959 Di-iff-Amino-,S-phenylpropionic acid, 480 N-Aminophthalimide, 38 3 -Amino-5i8-pregnane-20-one, 51... 

Reactions exhibiting diastereofacial selectivity, which occur when the imine or the enolate contains an endogenous stereocenter or a chiral auxiliary, have important applications for the synthesis of optically active 3-l ctams and 3-amino carboxylic acid derivatives. Early work by Furukawa et al. has demonstrated the viability of preparing optically active 3-amino acids from chiral imines. For example, the Schiff base derived from (5)-a-methylbenzylamine (110) reacts with Reformatsky reagent (111) to give, after hydrolysis and removal of the chiral auxiliary, 3-amino-2,2-dimethyl-3-phenylpropionic acid (112) in 33% ee (Scheme 21). Similar Reformatsky reactions have been performed using (-)-menthyl esters but the enantiomeric excess values are lower. ... 

Lobeline.—The results of feeding experiments with DL-[2- C]lysine and dl-[2- Clphenylalanine in Lobelia inflata have shown that these amino-acids are both specific precursors for the alkaloid lobeline (13). In further experiments, DL-[3- C]phenylalanine, [3- C]cinnamic acid, and [3- C]-3-hydroxy-3-phenylpropionic acid [as (9)] have been found to be specific precursors for lobeline (13). These results are consistent with the anticipated pathway " to lobeline illustrated in Scheme 2, with benzoylacetic acid (10) as the intermediate which couples with A -piperideine to give the intermediate (11). The probability of 3-hydroxy-3-phenylpropionic acid (9) being an intermediate in lobeline biosynthesis is increased by the isolation of this acid from L. inflata ... 

Tyrosine, HO.CeH4.CH2.CHNH2.COOH, which is a-amino-/3 p-hydroxyphenylpropionic acid, is an important product of the hydrolysis of many proteins. The acid has been synthesized from /3-phenylpropionic acid, C6H5.CH2.CH2.COOH, which can be prepared from benzyl chloride by the use of the malonic ester synthesis. The first steps in the synthesis are indicated by the following formulas —... 

In a dry flask were added 855 mg tosylamide (5 mmol), 84 mg DABCO (0.75 mmol), and 58.5 mg La(0Tf)3-H20 (0.1 mmol) together with 900 mg 4-A molecular sieves. Then 2.5 mL wo-PrOH, 505 fiL benzaldehyde (5 mmol), and 450 /u-L methyl acrylate (5 mmol) were added, and the reaction mixture was stirred for 48 h at ambient temperature. The mixture was Altered through a thin layer of Celite, which was rinsed three times with 10 mL wo-PrOH. The solvent was evaporated, and to the crude mixture were added 25 mL methanol and 10 mL 1 M sulfuric acid. The solution was stirred for 1 h, and then methanol was evaporated. The remaining acidic solution was diluted with water and extracted with dichloromethane (3 x 30 mL). The organic phase was then successively washed with saturated NaHCOs, 1 M NaOH, water, and saturated NaCl solution and dried over Na2S04. Evaporation of the solvent gave 1.38 g pure methyl Q -methylene-)8-[(/ -toluenesulfonyl)-amino]-3-phenylpropionate as a white crystalline material, in a yield of 80%, m.p. 76-77°C. 

CAS 673-06-3 EINECS/ELINCS 211-603-5 Synonyms Alanine, phenyl-, D- a-Aminohydrocinnamic acid D-o-Amino-p-phenylpropionic acid D-P-Phenylalanine (R)-(+)-Phenylalanine D-p-Phenyl-a-aminopropionic acid Empirical C9H11NO2 Formula C6HsCH2CH(NH2)C02H Properties Wh. cryst. powd., needles or prisms very sol. in 95% ethanol sol. in water si. sol. in methanol, petrol, ether m.w. 165.21 m.p. 273-284 C (dec.) b.p. 295 C (sublimes) ref. index 1.600 Toxicoiogy LD50 (IP, rat) 5452 mg/kg, (IV, mouse) 2100 pg/kg low toxicity by IP route may cause eye/skin irritation may be harmful by ing., inh., skin absorp. may cause Gl effects, hypermotility, diarrhea, nausea, vomiting TSCA listed... 

Amino-3-phenylbutyric acid, A"18.2 2-Amino-2-methyl-2-phenylpropionic acid, A40.3... 

Fig. 9. Structures of phenylalanine (1 ) and of phenylalanine analogs discussed in the text. ( ), 5-(l-amino-2-phenylethyl)tetrazole ( ), (1-amino-2-phenylethy1) phosphonic acid ( ), (l-amino-2-phenylethyl)phosphonous acid ( ), a-aminooxy-8-phenylpropionic acid ( ), a-hydrazino-6-phenylpropionic acid (7 ), 3-methylene-phenylalanine (S), (1,4-cyclohexadienyl)-alanine ( ), o-carboranylalanine (10), adamantylalanine.

I )-3-Fluoro-2-phenylpropionic Acid (4) Typical Procedure for Fluorodeamination of a-Amino Acids with Hydrogen Fluoride/Pyridine " ... 

Taxane alkaloids are made up of a terpenoid core and a phenylpropanoid (3-amino acid, joined by an ester bond. They can be classified according to the carbon-carbon connectivity of the terpenoid core and the type of the side-chain. Thus, the diterpenoid core can be of the taxane- (Tables 3-8), 11 (151 )abeotaxane-(Table 10), 2(3->20)abeotaxane-(Table 2) or 3-11-cyclotaxane (Table 9) type, whereas the side chain can be Winterstein s add [L(R) (3-dimethylamino-P-phenylpropionic add] or N, A/-dimethylphenylisoserine (2R, 3S (threo) a-hydroxy-3-dimethylamino-P-phenylpropionic acid). Further modification occurs in the... 

The alternative [2 + 2] cycloaddition route to azetidinones, using chloro-sulphonyl isocyanate and functionalized alkenes, has been further used in syntheses of /8-lactam antibiotics. Asymmetric induction in the formation of /3-amino-aa-dimethyl-/8-phenylpropionic acid has been achieved, using a Reformatsky reagent and a chiral Schifif base, the reaction proceeding through a /3-lactam intermediate. ... 

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