Ketones ninhydrin

Some of the innumerable reagents used in TEC are based on reactions with more or less well-established mechanism. Eor example, sodium iodobismuthate (Dragendorff reagent) is widely used among others for alkaloids and quaternary ammonium compounds, 4-dimethylaminobenzaldehyde for primary amines and amino acids, 2,4-dinitrophenylhydrazine for aldehydes and ketones, ninhydrin for amino acids and some antibiotics, fluorescamine for primary and secondary amines, phosphomolybdic acid for lipids, various steroids, and other compounds, chlorine vapor followed by Kl/starch for amines and amides. More complex is the mechanism of the reactions with some other reagents, containing high concentrations of sulfuric acid, vanillin/sulfuric acid, phosphoric acid, aluminum chloride, antimony(III)... 

Dissolve 50 mg cadmium acetate in a mixture of 5 ml DW and 1 ml glacial acetic acid and dilute with ethyl methyl ketone to 50 ml. Immediately before use add and dissolve sufficient Ninhydrin to produce a soln. containing 0.2% w/v. 

The triketone shown here is called ninhydrin and is used for the detection of amino acids. It exists in aqueous solution as a monohydratc. Which of the three ketones is hydrated and why ... 

Indanocyclone (1). Mol. wt. 2fi6..11, m.p. 205 206°. Prepared from ninhydrin and diben yl ketone and cthanolic potassium hydroxide. ... 

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. 

Ostreocin-D is a colorless amorphous solid, positive to ninhydrin. This compound possesses optical activity with a specific rotation of -f16,6 in water (c 0,12, T = 23°C), as well as an UV absorption spectrum exhibiting two maxima, at 234 (e 35000) and 263 nm (e 22000), The UV absorptions together with NMR spectra indicate that ostreocin-D has conjugated diene and ketone functionality analogous with palytoxin [23],... 

The approach using cyclodextrin as a binding site has also been developed. Cyclodextrins are widely utilized in biomimetic chemistry as simple models for an enzyme because they have the ability to form inclusion complexes with a variety of molecules and because they have catalytic activity toward some reactions. Kojima et al. (1980, 1981) reported the acceleration in the reduction of ninhydrin and some dyes by a 1,4-dihydronicotinamide attached to 3 Cyclodextrin. Saturation kinetics similar to enzymatic reactions were observed here, which indicates that the reduction proceeds through a complex. Since the cavity of the cyclodextrin molecule has a chiral environment due to the asymmetry of D-glucose units, these chiralities are expected to be effective for the induction of asymmetry into the substrate. Asymmetric reduction with NAD(P)H models of this type, however, has not been reported. Asymmetric reduction by a 1,4-dihydronicotinamide derivative took place in an aqueous solution of cyclodextrin (Baba et al. 1978), although the optical yield from the reduction was quite low. Trifluoromethyl aryl ketones were reduced by PNAH in 1.1 to 5.8 % e.e. in the presence of 3-cyclodextrin. Sodium borohydride works as well (Table 18). In addition to cyclodextrin, Baba et al. also found that the asymmetric reductions can be accomplished in the presence of bovine serum albumin (BSA) which is a carrier protein in plasma. 

Formation of spiro-pyrrolidines/pyrrolizidine has been achieved under micro-wave exposure by using the alkene unit of Baylis-Hillman adduct of ninhydrin with sarcosine/proline and various activated ketones through 1,3- dipolar cycloaddition reactions (Ramesh et al., 2007). 

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