A-Aminovaleric acid

CH3.(CH2)2.C(C02.C2Hs)(C0.N3) mw 198.23 N 21.20% OB to CO2 -153.36% yel oU, expl. Sol in eth and CCI4. Prepn is by reacting the K salt of the half (or mono) ethyl ester of propyl malonic acid with nitrous acid Refs 1) Beil, not foxmd 2) T. Curtius W. Lehmann, Transformation of alkylated malonic acids into ct-amino acids. III. Synthesis of a-aminovaleric acid, propylmalonylazidic acid. .. , JPraktChem 125, 211-302 (1930) CA 24, 3215(1930)... 

The best evidence that protein O-methyltransferase methylates the carboxyl groups of aspartic and glutamic acid residues in proteins comes from treating the enzyme methylation product with lithium borohydride followed by hydrolysis in 6N HC1. Two new hydroxy amino acids, y-hydroxy-a-aminobutyric acid and S-hydroxy-a-aminovaleric acid, were obtained (183). 

Norvaline. 2-Aminmrateric acid a-aminovaleric acid 2-aminopentanoic acid. C-H,NO, mol wt 117 15. C 51.26%, H 9.47%, N 11.96%, 6 27.32%. CH,(CH,),CH-(NHj)COOH. Prepd by treating butyraldehyde ammonia with HCN and HCh Slimmer, Bee. 35. 404 (1902) from 2-acetylvaleric acid ethyl ester Hamlin, Hartung, J. BioL Chem. 145, 349 (1942) from acetamidomalonic acid diethyl... 

Amino-5-ureidovaleric acid a-Amino-5-ureidovaleric acid L-(+)-2-Amino-5-ureidovaleric acid. See Citrulline 2-Aminovaleric acid a-Aminovaleric acid L-(+)-2-Ami no valeric acid. See L-Norvaline Aminox . See Diphenylamine-acetone Aminoxid A 4080. See Cocamine oxide Aminoxid WS 35. See Cocamidopropylamine oxide... 

CAS 6600-40-4 EINECS/ELINCS 229-543-3 Synonyms 2-Aminopentanaoic acid a-L-Aminopentanoic acid (S)-(+)-2-Aminopentanoic acid 2-Aminovaleric acid a-Aminovaleric acid... 

Molecular imprinting is not limited to organic polymer matrices, but can also be applied to silica-based materials and even proteins. Proteins freeze-dried in the presence of a transition state analogue as template have been used successfully as catalysts, e.g., for the dehydrofluorination of a fluorobutanone. For instance, lyophilized 3-lactoglobulin imprinted in this manner with N-isopropyl-N-ni-trobenzyl-amine could accelerate the dehydrofluorination by a factor of 3.27 compared to the non-imprinted protein see Table 5 [62]. In a similar procedure, BSA was imprinted with N-methyl-N-(4-nitrobenzyl)-S-aminovaleric acid and showed an enhancement of the catalytic effect by a factor of 3.3 compared to the control protein for the same reaction see Table 5 [113]. 

Baneqee A, Das AK, Drew MGN, Baneqee A. Supramolecular parallel 8-sheet and amyloidlike fibril forming peptides using S-aminovaleric acid residue. Tetrahedron 2005 61 5906-5914. 

In principle every compound with an amino and a carboxy group can be used for such purpose ranging from simple co-amino acids [e.g., 5-aminopentanoic acid (6-aminovaleric acid) (1, n = 3)]1541 or 6-aminohexanoic acid (e-aminocaproic acid) (1, n = 4)]135,57,4 791 and related derivatives of 3-aminobenzoic acid 14801 or more sophisticated structures. A few examples (1-6) are shown in Scheme 28. Numerous cyclic turn mimetics have been developed in the past years and for details on this subject the reader is directed to Vol. E 22c, Section 12. To explore the rigidification introduced by nonnatural amino acids or equivalent structures into cyclic peptides, a careful NMR conformational analysis is required, since frequently the so-called p-turn mimetics do not enable such turns to be established, conversely other secondary structure elements may be induced.14811... 

The dimethylene replacement 4 is used to investigate the influence of rigidity. The use of 5-aminovaleric acid as a Glytj)[CH2—CH2] GIy replacement has been extended to other coamino acids as a means to influence the distance between crucial amino acid residues, and to function as a flexible spacer, replacing parts of the peptide. 

Aminouracil, a 155 2-Aminovaleric acid, a253 5-Amino valeric acid, a254 Amyl compounds, see Pentyl Amyl alcohol, p37 act-Amyl alcohol, ml53 sec-Amyl alcohol, p38 tert-Amyl alcohol, ml54 tert-Amylamine, d601... 

Salts of a-oxo-S-aminovaleric acid and a-oxo-e-aminocapric acid92 93 exist as such in the solid state, but in solution they are in equilibrium with the cyclic compounds, J 1-pyrroline-2-carboxylic acid and J1Tpiperideine-2-carboxylic acid, respectively.94... 

Glutamic acid decarboxylase was assayed in a final volume of 100 / L containing 40 /tL of 200 mAf potassium phosphate buffer (pH 6.8), 10 / L of 5 mM L-glutamic acid, 5 / L of 0.2 mAf pyridoxal 5 -phosphate, 40 /tL of homogenate (2 mg protein/mL), and 1 fig of gabaquline (inhibitor of y-aminobutyric acid degradation). The reaction was stopped by the addition of 10 fiL of 100% trichloroacetic acid. After centrifugation, 5 fiL of standard 8-aminovaleric acid solution and 90 fiL of o-phthaldehyde solution (2 mg/mL 0.4 M borate buffer, pH 10.4) was added and the mixture was allowed to react for 3 to 5 minutes before injection of 20 fiL into the HPLC system. The reaction was linear for 20 minutes. 

Some relationships between the dipole moment and molecular structure have also been found in the case of aliphatic compounds. In the first instance we may mention the two methyl esters of a- and 8-aminovaleric acid. We should expect from the results for the aminobenzoic acids that in an open chain the moment of the 8-ester would be greater than that of the a-ester, while in a chain joined into a ring the moments should be about the same. The values obtained... 

L-a-amino-/3-phenylbutyric acid, a, /3-diaminobutyric acid L-a, jJ-diaminopropionic acid, / -aminopropionic acid d-aminovaleric acid, 2-aminohexenoic acid, 6-diazo-5-oxo-amino-hexanoic acid D-a-aminoadipic acid... 

The oxidation product has been isolated as its 2,4-dinitrophenylhydrazone and corresponds with -keto-6-aminovaleric acid. Putrescine, arginine, Manske s 1 (+) acetylornithine (118) and other related amino acids are oxidized much less readily if at all. The same authors have extracted an ornithine dehydrogenase from the young roots of Datura tatula. It requires the cooperation of a coenzyme not yet identified, and appears unable to oxidize putrescine and amino acids other than ornithine and to a lesser extent glutamic. Either of these systems, or the two linked into a H-transfer chain, would seem able to catalyze the oxidation of ornithine in the living tissues. No carbon dioxide was released from ornithine by the poly-phenolase system but on addition of an unwashed belladonna tissue-suspension carbon dioxide was liberated, presumably by decarboxylation of the a-keto-5-aminovaleric acid formed by the oxidation. 

Ornithine, NH2.CH2.CH2.CH2.CHNH2.COOH, a, 5-di-aminovaleric acid, and lysine, a, e-diaminocaproic acid, are obtained from proteins. The former is converted into putrescine, NH2(CH2)4NH2, and the latter into cadaverine, NH2(CH2)sNH2, by putrefactive bacteria. 

The first total syntheses of 32 were performed by Spath and co-workers (97.98) and by Hanford and Adams (99). Another synthesis was described by Munoz and Madronero (100). From a biogenetic point of view, some syntheses under physiological conditions are very interesting, for example, (1) from 8 -pyrroline and o-aminobenzaldehyde at pH 5 (84,101,102) or (2) from a-keto-8-aminovaleric acid and o-aminobenzaldehyde (103). Compound 32 can also be prepared by reduction of deoxyvasicinone (88,104,137) or by starting from vasicine (via chlorodeoxyvasicine) (105) or from vasicinone (via chlo-rovasicinone) (88). Sattarova et al. (106) reported a method for the quantitative determination of deoxyvasicine hydrochloride. 

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