Butyric acid, 3-Amino-3-methyl

C21. Crumpler, H. R., Dent, C. E., Harris, H., and Westall, R. G., P-aminoiso-butyric acid (a-methyl-p-alanine) a new amino-acid obtained from human urine. Nature 167, 307-308 (1951). 

Quaternary salts of the substances represented by tliese formulae have been prepared by Kogl, Veldstra and van der Laan as well as of the next lower homologues, the substituted butyraldehydes, and the methyl ethers of both series. Their pharmacological activities were negligible in comparison with that of muscarine, but as six stereoisomeric forms may be produced in each synthesis, the inactivity may be due to stereoisomerism, just as in the case of threonine (a-amino-)3-hydroxy-butyric acid) where West and Carter found that only the d —) form is... 

The interaction with both synthetic and naturally occurring amino acids has been studied extensively glycine (138, 173, 219-221), a-(173, 219) and /3-alanine (138, 220), sarcosine (219), serine (222), aspartic acid (138, 173, 222-226), asparagine (222), threonine (222), proline (219), hydroxyproline (219), glutamic acid (138, 222-225), glutamine (222), valine (219, 227), norvaline (219), methionine (222, 226), histidine (228, 229), isoleucine (219), leucine (219, 230), norleu-cine (219), lysine (222), arginine (222), histidine methyl ester (228), phenylalanine (138, 222), tyrosine (222), 2-amino-3-(3,4-dihydroxy-phenyl jpropanoic acid (DOPA) (222), tryptophan (222), aminoiso-butyric acid (219), 2-aminobutyric acid (219,231), citrulline (222), and ornithine (222). 

Moaddel, R., Clorx, J.-F., Ertem, G., Wainer, I. W. Multiple receptor liquid chromatographic stationary phases the co-immobilization of nicotinic receptors, y-amino-butyric acid receptors, and N-methyl-D-aspartate receptors. Pharm Res 2002, 19, 104-107. 

AMINO-N-METHYL-l,2,5-SELENADIAZOLE-3-CARBOXAMIDE see MGL600 2-AMINO-4-(METHYLTHIO)BUTYRIC ACID see MDT750... 

ETHATO-7-(2-HYDROXY-3-((l-METHYLETHA L)AMINO)PROPOXY)-4-BENZOFUKANAT) ETHANONE see ELI600 a-ETHYL-p-(HYDROXYMETHYL)-l-METHYL-IMIDAZOLE-5-BUTYRIC ACID, y-LACTONE see PIFOOO... 

C9H14N20 4-methyl-2H-imidazole-1-oxide-2-spirocyclohe 205692-62-2 25.00 1.0150 2 17845 C9H17N04 g-(boc-amino)butyric acid 57294-38-9 23.33 1.0303 2... 

The 2-D TLC was successfully applied to the separation of amino acids as early as the beginning of thin-layer chromatography. Separation efficiency is, by far, best with chloroform-methanol-17% ammonium hydroxide (40 40 20, v/v), n-butanol-glacial acetic acid-water (80 20 20, v/v) in combination with phenol-water (75 25, g/g). A novel 2-D TLC method has been elaborated and found suitable for the chromatographic identification of 52 amino acids. This method is based on three 2-D TLC developments on cellulose (CMN 300 50 p) using the same solvent system 1 for the first dimension and three different systems (11-IV) of suitable properties for the second dimension. System 1 n-butanol-acetone -diethylamine-water (10 10 2 5, v/v) system 11 2-propanol-formic acid-water (40 2 10, v/v) system 111 iec-butanol-methyl ethyl ketone-dicyclohexylamine-water (10 10 2 5, v/v) and system IV phenol-water (75 25, g/g) (h- 7.5 mg Na-cyanide) with 3% ammonia. With this technique, all amino acids can be differentiated and characterized by their fixed positions and also by some color reactions. Moreover, the relative merits of cellulose and silica gel are discussed in relation to separation efficiency, reproducibility, and detection sensitivity. Two-dimensional TLC separation of a performic acid oxidized mixture of 20 protein amino acids plus p-alanine and y-amino-n-butyric acid was performed in the first direction with chloroform-methanol-ammonia (17%) (40 40 20, v/v) and in the second direction with phenol-water (75 25, g/g). Detection was performed via ninhydrin reagent spray. 

The formation of a quaternary salt (7) upon heating 2,3-0-isopropylidene-5-0-(p-tolylsulfonyl)adenosine, observed by Clark, Todd, and Zussman and referred to elsewhere in this review, accounts for the low yield, since this monomolecular quaterni-zation takes place much more rapidly than bimolecular displacement of the p-tolyl-sulfonyloxy group by the methyl mercaptide ion. Recently, this difficulty has been overcome and a good yield of L-2-amino-4-(5-thioaden-5-yl)butyric acid obtained by the reaction of (9b) with the disodium salt of homocysteine in liquid ammonia. This compound had also been prepared enzymically. ... 

L-Phosphinothricin, the active ingredient of the broad-spectrum herbicide Basta (AgrEvo), can be obtained through enzymatic transamination of the corresponding oxoacid, 2-oxo-4-[(hydroxy)(methyl)phosphinoyl]butyric acid, in a coupled system with aspartate aminotransferase (AAT) and 4-aminobutyrate 2-ketoglutarate transaminase (E.C. 2.6.1.19) from E. coli (Fig. 12.7-6)[37 . In solutions containing 10% substrate, 85 % conversion was reached with only < 3 % amino acid by-products. For... 

Amino-4-(methyl- Se-seleno)butanoicacid. (S)-2-Amino-4-(methylselenyl- e)butyric acid Butanoic acid, 2-amlno-4-(methylseleno- Se)-, (S)- L-Seleno-methionine ( Se) L-Selenomethioninum ( Se) Seleno-methionine Se-in]ection Selenomethionine Se Selenomethioninum f Se) Selenometionina ( Se) L-( Se)-Selenothionine Sethotope. Selenomethionine Se is used as a diagnostic aid and radioactive... 

Peak identification I = cysteic acid 2 = aspartic acid 3 = glutamic acid 4 = S-carboxy-methyl cysteine 5 = asparagine 6 = serine 7 = glutamine 8 = histidine 9 = threonine fO = glycine 21= arginine 22 = 3-alanine 23 = tyrosine 24 = alanine 25 =a-amino butyric acid 26 = tryptophan 27 = methionine 28 = valine 29 = phenylalanine 20 = ammonia 22 = isoleucine 22 = leucine 23 = ornithine 24 = lysine. Chromatograms courtesy of P. Lindroth and K. Mopper. 

Amino-2-hydroxy[4- C]butyric acid (the corresponding aldehyde has been condensed with o-aminobenzaldehyde to give vasicine 4-hydroxy-[2- C]glutamic acid (found with vasicine in Linaria yw/garis ), N-methyl-anthranilic acid, and N-formylanthranilic acid have been tested as vasicine precursors in A. vasica, without success. 

The D-enantiomer of 393 was obtained in an identical sequence of reactions starting frc m 2,3-0-isopropylidene-4-deoxy-D-threitol (395). This compound was prepared from L-threonine (394) in the following way the amino acid was deaminated to 25 3/ -dihydroxy-butyric acid. Esterification of the carboxyl group and protection of both hydroxyl groups with an isopropylidene grouping gave methyl 4-deoxy-2,3-0-isopropylidene-D-threonate. Reduction of the ester group afforded 395 smoothly. 

There is also a later report by the same group regarding the use of a related catalyst 127 in the Michael addition of a-nitro ketones to enones (Scheme 6.19). In this case, a variety of peptides were tested as eatalysts but the best results were obtained with pentapeptide 127, in whieh, among many other different changes, the a-amino iso-butyric acid was employed instead of tert-leucine for the p-turn inducer sequence an additional modified arginine and a phenylalanine methyl ester were incorporated at the NH2 and the CO2H ends respectively. This catalyst furnished the final Michael adducts with moderate enantioselectivities, albeit in good yields in many cases. 

Fig. 2. The elution pattern of a standard mixture of OPA-derivatized primary amines, separated on a 5 (Jim Nucleosil C-18 column (200 X 4.6 mm id). The flow-rate was 1 mL/min employing the indicated gradient of metlianol and Na phosphate buffer (50 mA4, pH 5.25). Each peak represents 39 pmol except for those indicated below. 1, glutathione 2, cysteic acid 3, O-phosphoserine (19.5 pmol) 4, cysteine sulfinic acid 5, aspartic acid 6, asparagine (19.5 pmol) 7, glutamic acid 8, histidine 9, serine 10, glutamine 11, 3-methyl-histidine 12, a-aminoadipic acid (9.8 pmol) 13, citrulline (9.8 pmol) 14, carnosine 15, threonine,glycine 16, O-phosphoethanolamine 17, taurine (19.5 pmol) 18, p-alanine (19.5 pmol) 19, tyrosine 20, alanine 21, a-aminoisobutyric acid 22, aminoisobutyric acid 23, y-amino-ii-butyric acid 24, p-amino-u-butyric acid 25, a-amino-butyric acid 26, histamine 27, cystathione (19.5 pmol) 28, methionine 29, valine 30, phenylalanine 31, isoleucine 32, leucine 33, 5-hydroxytryptamine (5-H i ) 34, lysine. The chromatographic system consisted of a Varian LC 5000 chromatograph and a Schoeffel FS 970 fluorimeter.

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