Fluorogenic reaction of sulfite with o-phthalaldehyde.

Takadate, Akira; Fujino, Hiroyuki; Obasa, Masahiro; Goya, Shujiro

doi:10.1248/cpb.34.1172

Cited by 4 publications

(3 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The product of the reaction of SO 3 2-with OPA absorbs at 360 nm. Fluorescence comparable to that in the presence of SO 3 2has been reported 67 in the presence of S 2 O 4 2and S 2 O 5 2-, but negligible fluorescence has been observed for S 2-, SO 4 2-, SCN -, S 2 O 3 2-, S 2 O 6 2-, S 2 O 7 2-, and S 2 O 8 2-.…”

Section: Reactions With Thiols and Other Sulfur Compoundsmentioning

confidence: 53%

See 1 more Smart Citation

Reactions of Orthophthalaldehyde with Nucleophiles

Zuman

2004

Chem. Rev.

122

View full text Add to dashboard Cite

Contents 1. Introduction 3217 2. Addition of a Single Nucleophile to OPA 3218 2.1. Addition of Water and Hydroxide Ions 3218 2.2. Addition of Alcohols 3219 2.3. Addition of Ammonia and Primary Amines 3219 2.4. Reactions with Hydrazine 3219 2.5. Reactions with Amino Acids 3220 2.6. Reactions with Amides, Urea, and Thiourea 3221 2.7. Reactions with Carbanions 3221 2.8. Reactions with Thiols and Other Sulfur Compounds3222 3. Reactions in the Presence of Two Nucleophiles 3223 3.1. Reagents 3224 3.1.1. Role of the Carbonyl Compound 3224 3.1.2. Stability of the Mixed Reagent 3224 3.1.3. Structure of the Thiol 3224 3.1.4. Structures of Amino Acids and Amines 3225 3.2. Sequence of Addition 3225 3.3. Reaction Medium 3225 3.4. Kinetics of the Formation of the Primary Product 3227 3.5. Consecutive Reactions of the Isoindole DerivativesStability of the Product of the Analytical Reaction 3228 3.6. Proposed Reaction Schemes 3232 3.6.1. Scheme Proposed by Simmons and Johnson 3232 3.6.2. Scheme Proposed by Wong, Sternson, and Schowen 3232 3.6.3. Scheme Proposed by Sternson, Stobaugh, and Repta 3233 3.6.4. Scheme Proposed by Gladilovich, Kartsova, and Zakharova 3233 3.6.5. Scheme of the Degradation of the Derivative of 2-Mercaptoethanol 3233 3.6.6.Scheme for Autoxidation of the Isoindole 3234 3.6.7. Conclusions Regarding Reaction Scheme 3234 3.7. Techniques Used 3234 3.8. Other Uses of the Reagent Formed in Reaction of OPA with Thiols 3235 3.9. Reagents Prepared by Reaction of Orthophthalaldehyde with Nucleophiles Other than Thiols 3235 3.10. Some Biochemical Applications 3236 4. Conclusions 3237 5. Acknowledgment 3237 6. References 3237

show abstract

Section: Reactions With Thiols and Other Sulfur Compoundsmentioning

confidence: 53%

“…Formation of some fluorescent species has also been observed 67 in the presence of OPA with some inorganic sulfur compounds. Thus, in reaction of SO 3 2-the fluorescence intensity increased with increasing pH up to about pH 10 and then decreased.…”

Section: Reactions With Thiols and Other Sulfur Compoundsmentioning

confidence: 85%

Reactions of Orthophthalaldehyde with Nucleophiles

Zuman

2004

Chem. Rev.

122

View full text Add to dashboard Cite

show abstract

“…In comparison to the most widely used photometric detection, fluorometric detection often provides an improved signal-to-noise ratio combined with a higher selectivity. Fluorometric detection was applied to the determination of sulfite, after its derivatization with N -(9-acridinyl) maleimide, − with monobromobimane, with phthalaldehyde only, and with phthalaldehyde/ethanolamine . The reaction of N -(9-acridinyl) maleimide with sulfite takes a relatively long reaction time.…”

mentioning

confidence: 99%

Sensitive and Selective Flow Injection Analysis of Hydrogen Sulfite/Sulfur Dioxide by Fluorescence Detection with and without Membrane Separation by Gas Diffusion

Mana

Spohn

2001

Anal. Chem.

View full text Add to dashboard Cite

Highly sensitive and selective FIA flow injection analysis procedures for the determination of sulfite/hydrogen sulfite/sulfur dioxide were developed on the basis of an in situ-generated o-phthalaldehyde (OPA)/ammonium reagent and fluorescence detection. The highest sensitivity was achieved at an excitation wavelength of 330 nm, an emission wavelength of 390 nm, and at pH 6.5. Sulfite concentrations between 2.5 nM and 5 microM can be determined with relative standard deviations between 10.5 and 1.0% (n = 5, confidence level alpha = 0.05) by utilization of a reagent that contains 0.2 mM OPA and 0.4 M NH4Cl in 50 mM potassium phosphate buffer. A concentration of 0.1 mM sulfite can be selectively detected in the presence of thiosulfate, thioglycolate, tetrathionate, cysteine, and ascorbate. The fluorometric sulfite detection was combined with a membrane gas diffusion step to improve the selectivity with respect to nonvolatile fluorescing substances. The total sulfite content can be quantitatively separated as sulfur dioxide into an acceptor solution before its flow detection. Between 40 nM and 0.1 mM sulfite can be determined. After 1,000-fold dilution, the total sulfite content can be determined in white and red wines.

show abstract

Fluorometric measurement of aqueous ammonium ion in a flow injection system

1989

View full text Add to dashboard Cite

A shipboard fluorometric flow analyzer has been developed for near-real-time, high-resolution underway measurement of ammonium in seawater. The fluorometric method is based on the reaction of ammonium with o-phthaldialdehyde (OPA) and sulfite. The reagents used in this method have been modified to suit seawater analysis. This method shows no refractive index and salinity effect from seawater samples. The potential interferences in seawater have been studied, and their effects have been reduced. The instrument response is linear over a wide range of ammonium concentration. The limit of detection of 1.1 nM was estimated in laboratory using ammonium standards prepared in distilled water. It should be noted that application of this method to lowlevel ammonium measurement requires a correction of interference species, such as amino acids. The sample throughput is 3600 h -1 . The system can be used for both freshwater and seawater samples and has been used to monitor the distribution of ammonium in Florida coastal waters around an oceanic wastewater outfall.Ammonium is an essential nutrient in the marine environment. Phytoplankton generally prefer ammonium over nitrate, which requires additional energy to reduce to ammonium during assimilation. 1-3 However, high concentrations of ammonia are toxic to marine organisms such as fish, 4 shrimp, 5 abalone, 6 and sea urchin, 7 especially larvae or juveniles of these species. Water quality monitoring requires accurate measurements of the concentration of ammonium in the coastal environment; 8 however, both physical and biological processes, such as biological uptake and release, 9,10 atmospheric deposition, air-sea gas exchange, 11,12 and wastewater discharge, 13 rapidly change the ammonia concentrations in both space and time. Development of a shipboard analyzer that can perform near-real-time, high-resolution underway measurements of ammonium in coastal water is urgently needed.The most common technique used to measure ammonia in seawater is the indophenol blue method using the Berthelot reaction; 14,15 however, this technique has low sensitivity (LOD 0.6 µM) and a high reagent blank. [16][17][18] An ammonia electrode was found easy to operate, 19 but it requires long equilibration times and provides low sensitivity (LOD 0.2 µM). To increase sensitivity, a solvent extraction method 20 was developed, but the procedure is time-consuming and labor-intensive. Recently, a long-path liquid waveguide capillary cell 21 was used to improve the sensitivity (LOD 5 nM), but the problems associated with the indophenol blue still remained. In 1971, Roth 22 developed a fluorescent method for determination of amino acid and ammonia in which o-phthaldialdehyde (OPA) reacts with mercaptoethanol to produce a strongly fluorescent compound. This method has been adapted for a variety of applications. [23][24][25]26 In 1989, Dasgupta 27 modified this method by replacing mercaptoethanol with sulfite and provided a method with higher sensitivity for ammonia and greater selectivity over amino ac...

show abstract

Fluorogenic reaction of sulfite with o-phthalaldehyde.

Cited by 4 publications

References 0 publications

Reactions of Orthophthalaldehyde with Nucleophiles

Reactions of Orthophthalaldehyde with Nucleophiles

Sensitive and Selective Flow Injection Analysis of Hydrogen Sulfite/Sulfur Dioxide by Fluorescence Detection with and without Membrane Separation by Gas Diffusion

Fluorometric measurement of aqueous ammonium ion in a flow injection system

Contact Info

Product

Resources

About