Determination of aliphatic amines in mineral flotation liquors and reagents by high-performance liquid chromatography after derivatization with 4-chloro-7-nitrobenzofurazan

Hao, F.; Lwin, T.; Bruckard, Warren J.; Woodcock, J.T.

doi:10.1016/j.chroma.2004.08.130

Cited by 23 publications

(10 citation statements)

References 3 publications

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“…Nucleophilic attack on 1 proceeds through a stepwise S N 2Ar mechanism, often with reversible addition of the nucleophile to formation of the intermediate σ-complex (Meisenheimer complex) and subsequent final product. 33 Although 1 and other electrophilic benzofurazan derivatives have been used extensively for labeling, modifying, and quantifying endogenous thiols, 34 they can also react with other nucleophiles including cysteine sulfenic acids, 35 amino groups, 36 and tyrosine hydroxyl groups 37 at neutral and basic pH ranges. In certain cases, if suitably nucleophilic groups are present near an NBD-labeled residue, the ligated NBD group can be transferred intramolecularly to adjacent nucleophilic residues.…”

Section: Resultsmentioning

confidence: 99%

Development of Selective Colorimetric Probes for Hydrogen Sulfide Based on Nucleophilic Aromatic Substitution

et al. 2013

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Hydrogen sulfide is an important biological signalling molecule and an important environmental target for detection. A major challenge in developing H2S detection methods is separating the often similar reactivity of thiols and other nucleophiles from H2S. To address this need, the nucleophilic aromatic substitution (SNAr) reaction of H2S with electron-poor aromatic electrophiles was developed as a strategy to separate H2S and thiol reactivity. Treatment of aqueous solutions of nitrobenzofurazan (7-nitro-1,2,3-benzoxadiazole, NBD) thioethers with H2S resulted in thiol extrusion and formation of nitrobenzofurazan thiol (λmax = 534 nm). This reactivity allows for unwanted thioether products to be converted to the desired nitrobenzofurazan thiol upon reaction with H2S. The scope of the reaction was investigated using a Hammett linear free energy relationship study, and the determined ρ = +0.34 is consistent with the proposed SN2Ar reaction mechanism. The efficacy of the developed probes was demonstrated in buffer and in serum with associated sub-micromolar detection limits as low as 190 nM (buffer) and 380 nM (serum). Furthermore, the sigmoidal response of nitrobenzofurazan electrophiles with H2S can be fit to accurately quantify H2S. The developed detection strategy offers a manifold for H2S detection that we foresee being applied in various future applications.

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Section: Resultsmentioning

confidence: 99%

Development of Selective Colorimetric Probes for Hydrogen Sulfide Based on Nucleophilic Aromatic Substitution

et al. 2013

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“…이를 위 해 amine분석을 위해 NBD-Cl를 사용했던 유도체화 방법을 변화시켜 응용하였다 [7]. 먼저 racemic leucine methyl ester HCl을 반응용매에 녹인 다음, NaHCO 3 를 base로 사용하여 해 당 NBD 유도체를 합성하였는데 …”

Section: 결과 및 고찰unclassified

Enantiomer Separation of α-Amino Acid Esters as Nitrobenzoxadiazole Derivatives Using Chiral Columns

윤원남¹,

김지연²,

이원재³

2013

KSBB Journal

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A new convenient derivatization method of α-amino acid esters as nitrobenzoxadiazole (NBD) derivatives for chiral resolution was introduced and the enantiomer separation of α-amino acid esters as NBD derivatives was performed by normal HPLC using chiral columns based on polysaccharide derivatives. The NBD derivatives were readily prepared by stirring NBD-Cl and α-amino acid methyl ester HCl with NaHCO 3 in ethanol. The performance of Chiralpak IA was superior to the other chiral stationary phases for enantiomer resolution of NBD derivatives of several α-amino acid methyl esters. Owing to fluorescence detection as well as strong UV absorption, it is expected that the convenient analytical method developed in this study will be very useful for enantiomer separation of α-amino acid esters as NBD derivatives on polysaccharide-derived chiral columns.

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“…HPLC another tool frequently used is slightly laborious and expensive, as it requires stringent purifications of samples and large amounts of solvents and washings of column. These methods often require derivatization of the amine (Zhao et al 2003;Hao et al 2004).…”

Section: Introductionmentioning

confidence: 99%

Spectrophotometric method for estimation of aliphatic primary amines in biological samples

Varma

Gaikwad

2007

World J Microbiol Biotechnol

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A method based on Rimini test for aliphatic amines was studied and developed for quantitative estimation of aliphatic primary amines. The method involves action of the amine with acetone to form schiff base which complexes with sodium nitroprusside to give violet colour. The absorption maximum in the visible range of the spectrum, for the reaction mixture was found to be 550 nm. The pH (8-11) and reaction time scan for the assay were optimized. A linear relation of concentration (0.2-3 mg/mL) of amine against absorbance at 550 nm was established. Interference due to other reaction components was negligible (±0.02 mg/mL) as compared to the sample in buffer. 1, 3-dimethyl butylamine was used as the model amine and the method was applied to other amines; it was observed that when electron-withdrawing substituents are present in the molecule the reaction is retarded, as the incubation time was longer. This method is useful for estimation of aliphatic primary amine in biological samples.

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Determination of aliphatic amines in mineral flotation liquors and reagents by high-performance liquid chromatography after derivatization with 4-chloro-7-nitrobenzofurazan

Cited by 23 publications

References 3 publications

Development of Selective Colorimetric Probes for Hydrogen Sulfide Based on Nucleophilic Aromatic Substitution

Development of Selective Colorimetric Probes for Hydrogen Sulfide Based on Nucleophilic Aromatic Substitution

Enantiomer Separation of α-Amino Acid Esters as Nitrobenzoxadiazole Derivatives Using Chiral Columns

Spectrophotometric method for estimation of aliphatic primary amines in biological samples

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