JS-amino acids

Defen sins j Basic antibiotic peptides of 20-33 amino j acids Apparently kill bacteria by causing membrane damage... 

Two important azo dye intermediates, Amino J acid and Amino G acid, are also produced by the Bucherer reaction represented as follows ... 

Supplement 1955 3634-3793 Sulphonic acids Indigo-disulphonic acid (indigocarmine), 304. Amines, 308. Keto-ammes Pyramidone, 452. Allan-toin, 474. Murexide, 499. Amino-carboxylic acids Histidine, 513. j Hydrazines, 531. Azo compounds, 535. 1... 

J-acid (6-amino-l-naphthol-3-sulfonic acid [87-02-5]) (16), and gamma acid (7-amino-1-naphtho1-3-su1fonic acid [90-51-7]) (17). 

Interesting regioselectivities have been known for more than 100 years for azo coupling reactions with aminonaphthol derivatives such as 6-amino-4-hydroxy-2-naphthalenesulfonic acid (12.136, y-acid), 7-amino-4-hydroxy-2-naphthalenesulf-onic acid (J-acid), and 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid (H-acid). They give two types of isomeric azo compounds depending on the pH-value of the... 

Knobler Y, Bittner S, Frankel M (1964) Reaction of N-carboxy-alpha-amino-acid anhydrides with hydrochlorides of hydroxylamine O-alkylhydroxylamines + amines syntheses of amino-hydroxamic acids amido-oxy-peptides + alpha-amino-acid amides. J Chem Soc 3941... 

Knobler Y, Bittner S, Virov D, Frankel M (1969) Alpha-aminoacyl derivatives of aminoben-zoic acid and of amino-oxy-acids by reaction of their hydrochlorides with amino-acid N-carboxyanhydrides. J Chem Soc C 1821... 

Reboud-Ravaux, M. Convert, O. Mazaleyrat, J.-P. Wakselman, M. Structural factors in the enzymic hydrolysis of cyclopeptides containing an ortho- or meta-amino benzoic acid residue. Bull. Soc. Chim. Fr. 1988, 267-271. 

Huber, J.W. and Gilmore, W.R, Optically active a-amino-phosphonic acids from ureidophosphonates, Tetrahedron Lett., 3049, 1979. 

Redmore, D., N-Benzyl-a-amino phosphonic acids, J. Org. Chem., 43,996,1978. 

Lukszo, J. and Tyka, R., New protective groups in the synthesis of 1-aminoal-kanephosphonic acids and esters, Synthesis, 239, 1977. 

Of far greater importance are the sulphonated aminonaphthols, in which the versatility conferred by the presence of both an amino and a hydroxy group makes them among the most important group of azo intermediates. Three are outstanding, namely, 6-amino-l-naphthol-3-sulphonic acid (4.16 J acid), 7-amino-l-naphthol-3-sulphonic acid (4-17 y acid) and H acid (4.2), which couple under the relevant conditions of pH at the arrowed positions. 

Piepponen TP, Skujins A. 2001. Rapid and sensitive step gradient assays of glutamate, glycine, taurine and y-amino-butyric acid by high-performance liquid chromatography-fluorescence detection with o-phthalaldehyde-mercap-toethanol derivatization with emphasis on microdialysis samples. J Chromatogr B 757 277-283. 

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. 

Fields EK (1952) The synthesis of esters of substituted amino phosphonic acids. J Am Chem Soc 74(6) 1528-1531... 

Hodson, P.V., B.R. Blunt, D.J. Spry, and K. Austen. 1977. Evaluation of erythrocyte d-amino levufinic acid dehydratase activity as a short-term indicator in fish of a harmful exposme to lead. Jour. Fish. Res. Board Can. 34 501-508. 

Mauzerall D, Granick S (1995) The occurrence and determination of delta-amino-levulinic acid and porphobilinogen in urine. J Biol Chem 219 435-446... 

The reversibility of the Bucherer reaction is utilised in the preparation of 2-p-tolylamino-5-hydroxynaphthalene-7-sulphonic acid (II) from 2-amino-5-hydroxynaphthalene-7-sulphonic acid or J acid (I) by heating with p-toluidine and sodium bisulphite solution ... 

S. Hanessian, C. Couture, and H. Wyss, Design and reactivity of organic functional groups. Utility of imidazolylsulfonates in the synthesis of monobactams and 3-amino nocardicinic acid, Can. J. Chem. (55 3613 (1985). 

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