2- aminonaphthalene-6-sulfonate

Seliskar C, Brand L (1971) Electronic spectra of 2-aminonaphthalene-6-sulfonate and related molecules. II. Effects of solvent medium on the absorption and fluorescence spectra. JACS 93 5414-5420... 

Amination of Schaeffer s acid (2-naphthol-6-sulfonic acid) (50) as its salt at 150-160 °C yields 2-aminonaphthalene-6-sulfonic acid, Bronner s acid (46c) (Scheme 11). 

The indole chromophore of tryptophan is the most important tool in studies of intrinsic protein fluorescence. The position of the maximum in the tryptophan fluorescence spectra recorded for proteins varies widely, from 308 nm for azurin to 350-353 nm for peptides lacking an ordered structure and for denatured proteins. (1) This is because of an important property of the fluorescence spectra of tryptophan residues, namely, their high sensitivity to interactions with the environment. Among extrinsic fluorescence probes, aminonaphthalene sulfonates are the most similar to tryptophan in this respect, which accounts for their wide application in protein research.(5)... 

Figure 4.6.2 The calixarene polyp with eight lactose arms binds tightly to quartz surfaces and binds the water-soluble aminonaphthalene-sulfonate fluorescence dye.

Wei, Z.X., and M.X. Wan. 2003. Synthesis and characterization of self-doped polyjamline-co-aminonaphthalene sulfonic acid) nanotubes. Appl Polym Sci 87 (8) 1297-1301. 

Many sulfonic acids, such as sul-fanilic, aminonaphthalene sulfonic, etc. 

Weber and Laurence (1953) have described a series of substances that although completely nonfluorescent in water solution become strongly fluorescent on adsorption by native serum albumin, denatured ovalbumin, filter paper, or alumina. They are also spontaneously fluorescent in certain solvents. These substances are derivatives of 3-chloro-6-meth-oxy-9-aminoacridine or of one of several aminonaphthalene sulfonic acids, in which one of the amino hydrogens has been substituted by a benzene ring derivative. The explanation of the behavior on adsorption lies apparently in that the radiative transition is forbidden for the nonplanar molecule but is allowed when the molecule lies on a plane as it presumably does on adsorption. This is extensively discussed by Forster (1951). Although the causes of the phenomenon are interesting in themselves, its practical applications may be of importance. Laurence and Rees (1953) have developed a method for the rapid and accurate determination of albumin in blood serum by fluorimetry using 1 N phenyl-aminonaphthalene-5 sulfonic acid. The detection of ovalbumin dena-turation by this method also deserves consideration. The appearance of fluorescence on adsorption of auramin O by nucleic acids has been described by Oster (1951). 

Nortemann, B., C. Bruhn, and H.-J. Knackmuss. 1986. Recruitment of complementary catabolic activities for mineralization of aminonaphthalene sulfonates and chloronitrophenols. EMBO Workshop Genetic Manipulation of Pseudomonads. Applications in Biotechnology and Medicine. 

Naphthionic acid (4-aminonaphthalene-l-sulfonic acid) [84-86-6] M 223.3, m > 300°(dec), pK 2.68. It crystallises from H2O as needles of the 0.5 hydrate. Salt solns fluoresce strongly blue. 

A bacterial strain BN6 oxidizes 5-aminonaphthalene-2-sulfonate by established pathways to 6-amino-2-hydroxybenzalpyruvate that undergoes spontaneous cyclization to 5-hydroxy-quinoline-2-carboxylate (Figure 2.2a) (Nortemann et al. 1993). 

FIGURE 2.2 Transformation of (a) 5-aminonaphthalene-2-sulfonate, (b) benzo[fc]thiophene, (c) 4-chloro-biphenyl, (d) 4-nitrotoluene, (e) 3,5-dichlor-4-methoxybenzyl alcohol, (f) 2,3-diaminonaphthalene in presence of nitrate, and (g) 3,4-dichloroaniline presence of nitrate. 

Nortemann B, A Glasser, R Machinek, G Remberg, H-J Knackmuss (1993) 5-hydroxyquinoline-2-carboxylic acid, a dead-end metabolite from the bacterial oxidation of 5-aminonaphthalene-2-sulfonic acid. Appl Environ Microbiol 59 1898-1903. 

An analogous pathway is used for the degradation of 5-aminosalicylate that is an intermediate in the degradation of 6-aminonaphthalene-2-sulfonate. Direct ring fission of both 5-aminosalicylate and 5-hydroxysalicylate can be accomplished by a salicylate 1,2-dioxygenase in Pseudaminobacter salicylatoxidans (Hintner et al. 2001). 

Aromatic azo compounds, many of which are sulfonated, are components of many commercially important dyes, colorants, and pigments, so that attention has been directed to their degradation and transformation. These compounds are often considered recalcitrant, although then-transformation has been accomplished by reduction to amines with scission of the Ar-N=N-Ar bond to produce arylamines. The amines may then be degraded, for example, 6-aminonaphthalene-2-sulfonate by dioxygenation and ring fission to 5-aminosalicylate (Hang et al. 1991). This is then... 

Haug W, A Schmidt, B Nortemann, DC Hempel, A Stolz, H-J Knackmuss (1991) Mineralization of the sulfonated azo dye mordant Yellow 3 by a 6-aminonaphthalene-2-sulfonate-degrading bacterial consortium. Appl Environ Microbiol 57 3144-3149. 

In addition, the formation of terminal metabolites may be adverse either for the organism itself, or for other organisms in the ecosystem. Microbial metabolites may also undergo purely chemical reactions to compounds that are terminal products. Examples include the formation of 5-hydroxyquinoline-2-carboxylate from 5-aminonaphthalene-2-sulfonate (Nortemann et al. 1993) or benzo[fc]naphtho[l,2- /]thiophene from benzothiophene (Kropp et al. 1994). Microbial metabolites may be toxic to both the bacteria producing them and to higher organisms. Illustrative examples of toxicity include the following ... 

As a diazonium component, aniline sulfonic acid may occasionally be replaced by 2-aminonaphthalene-l-sulfonic acid or by aniline. 

The use of pyridine during final coupling (pyridine coupling) is illustrated in the following abridged manufacturing specification for C. I. Direct Green 33, 34270 2-aminonaphthalene-8-sulfonic acid —> 3,5-xylidine- 2-ethoxy Cleve acid-6— A-acetyl H acid... 

Copper complexes of these materials or of analogous dyes derived from y acid (l-hydroxy-7-aminonaphthalene-3-sulfonic acid) confer gray-violet [9] and blue... 

Disazo dyes are obtained by using coupling components with a primary amino group and dimerization with phosgene [111]. The diazo components are prepared by exhaustive alkylation of amino methylated 2-aminonaphthalene-1 -sulfonic acid, followed by scission of the sulfonic acid group in the presence of mineral acids [112],... 

In the separation of oligosaccharides, sulfonic acids (mono-, di- or tri-) of aminonaphthalene have been used [29]. Polyuronic acids hke hyaluronic acid have also been characterized by CE [30]. 

The l-aminonaphthalene-4,8-disulfonic acid is precipitated as the neutral sodium salt by the addition of enough salt to make a 20 per cent salt solution (30° B6). The sulfonate is then filtered off. The l-aminonaphthalene-3,8-disulfonic acid is precipitated with hydrochloric acid as the acid sodium salt. If the whole mixture was limed, then the mother liquor is neutralized and evaporated to the point where salt separates. The supernatant liquid is poured off and allowed to crystallize at 20°C. The neutral sodium salt of 2-aminonaphthalene-4,8-disulfonic acid separates. This neutral salt is dissolved in water (24° Be solution) and precipitated by making the solution acid to Congo red with concentrated hydrochloric acid. The mixture is then allowed to cool, and the product is filtered off. 

Certain sulfonic acids may be cleaved by Na(Hg) thus l-aminonaphthalene-3,8-disulfonic acid can be reductively cleaved to l-aminonapththalene-3-sulfonic acid. The sulfonic group in the 8-position is more easily removed reductively than sulfonic groups in the 2-, 4-, or 6-positions [79]. 

Abbreviations AAO anodic aluminium oxides ANSA 5-aminonaphthalene-2-sulfonic acid APS—Ammonium persulphate ASA — Anthracene Sulfonic acids CB — conduction band CPs — conducting polymers CSA... 

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