A fluorescence flow injection method for the quantitation of cyanide: its application to the quantitation of bound cyanide in cassava using an immobilized linamarase bioreactor

Narinesingh, Dyer; Saroop, Sabrina; Ngo, T. T.

doi:10.1016/s0003-2670(97)00420-0

Cited by 5 publications

(4 citation statements)

References 18 publications

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“…Similarly, cyanide ions can be determined by measuring fluorescence of the 1-cyanoisoindole derivative, formed at pH 9 in a solution containing OPA and taurine. , This reaction was also utilized in a flow-injection method for determination of CN - ions in cassava. Limarase was used in a bioreactor to liberate cyanide ions bound in cassava …”

Section: 9 Reagents Prepared By Reaction Of Orthophthalaldehyde With ...mentioning

confidence: 99%

“…Limarase was used in a bioreactor to liberate cyanide ions bound in cassava. 151 The thiol can be replaced in the reaction with OPA by glycine. In the presence of cyanide ions the reagent, consisting of OPA and glycine, yielded a 1-cyanoisoindole derivative in a borate buffer at pH 8.2 containing 10% ethanol.…”

Section: Reagents Prepared By Reaction Of Orthophthalaldehyde With Nu...mentioning

confidence: 99%

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Reactions of Orthophthalaldehyde with Nucleophiles

Zuman

2004

Chem. Rev.

121

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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

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Section: 9 Reagents Prepared By Reaction Of Orthophthalaldehyde With ...mentioning

confidence: 99%

Section: Reagents Prepared By Reaction Of Orthophthalaldehyde With Nu...mentioning

confidence: 99%

Reactions of Orthophthalaldehyde with Nucleophiles

Zuman

2004

Chem. Rev.

121

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“…These reactions have primarily been applied to the detection of amines and amino acids, although NDA or OPA can also be used in conjunction with an excess of amino acid, e.g., taurine, to detect cyanide, as demonstrated by a number of flow injection schemes [3][4][5]. Ion exclusion chromatography with postcolumn derivatization [6], capillary electrophoresis (CE) of blood samples [7], and CE microchip of vapor and drinking water samples [8] are all examples of techniques which have taken advantage of OPA or NDA for the separation and detection of cyanide.…”

Section: Introductionmentioning

confidence: 99%

Separation of thiol and cyanide hydrolysis products of chemical warfare agents by capillary electrophoresis

Copper

Collins

2004

Electrophoresis

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The fluorescence derivatizing agent, o-phthalaldehyde (OPA), has been applied to the separation and detection of cyanide and several structurally similar thiols by capillary electrophoresis (CE)-laser induced fluorescence (LIF). Of particular interest to this investigation was the separation of 2-dimethylaminoethanethiol, 2-diethylaminoethanethiol, and cyanide, each of which are hydrolysis products or hydrolysis product simulants of the chemical warfare (CW) agents O-ethyl S-2-diisopropylaminoethyl methylphosphonothiolate (VX), O-isobutyl S-2-diethylaminoethyl methylphosphonothiolate (R-VX), and tabun (GA). Other structurally similar thiols simultaneously resolved by this method include 1-pentanethiol and 2-mercaptoethanol. Instrumental parameters were probed and optimum values for capillary length (50 cm) and inner diameter (75 microm), injection time (30 s) and field strength (15 kV) were determined. Sample stacking methods enabled detection limits of 9.3 microg/L for cyanide, 1.8 microg/L for 2-diethylaminoethanethiol, 35 microg/L for 2-dimethylaminoethanethiol, 15 microg/L for 2-mercaptoethanol, and 89 microg/L for 1-pentanethiol. The linearity of the method was verified over an order of magnitude and the reproducibility was found to be 3.0%.

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“…OPA was allowed to react with cyanide in the reaction coil (5.0 m) for 1 min, and the fluorescence intensity, using 40 ng mL -1 CNsolution, was 60% that observed in batch-type reactions. The batch measurements, however, required 5 min to reach a constant fluorescence intensity, while using this sensor one measurement cycle took approximately 150 s, approximately 1/8 the time of a similar HPLC analysis using OPA (16). Although the use of a longer reaction coil might increase the fluorescence intensity, the present measurement time is appropriate for an FIA system.…”

Section: Effect Of Buffer Solution Phmentioning

confidence: 95%

Continuous in Situ Cyanide Monitoring Using a Highly Sensitive and Selective FIA System

Nomura

Nagakubo

et al. 2000

Environ. Sci. Technol.

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A flow injection analysis (FIA) system incorporating a gas-diffusion membrane was fabricated for the detection of cyanide anion in aqueous samples. The principle of measurement is based on the reaction of o-phthalaldehyde (OPA) and cyanide in the presence of glycine to produce a fluorescent isoindole derivative. The cyanide concentration of the samples is thus proportional to the observed fluorescence intensity. Although extremely low levels of cyanide could be determined using this system (lower detection limit 0.4 ng mL-1 of CN-), measurements were affected by the presence of sulfite ion and thiols. Therefore, a gas-diffusion membrane was incorporated into the system to separate gaseous hydrogen cyanide from interferents in the sample. Consequently, this system displayed high selectivity for cyanide. The presence of sulfite ion (1 μg mL-1), 2-mercaptoethanol (0.1 μg mL-1), or 2-mercaptopropionic acid (10 μg mL-1) did not significantly increase the fluorescence intensity of cyanide solutions (16 ng mL-1). The sensor was then used for the rapid (150 s per measurement) detection of cyanide in samples of river water. A linear response (Kawashima bridge, y = 0.174x − 2.54E-2, r 2 = 0.999, n = 3; Yaba bridge, y = 0.170x + 2.75E-2, r 2 = 0.997, n = 3) was observed between the concentration of cyanide (0.4−40 ng) added to the samples and the response of the sensor. Furthermore, a device based on this FIA system was constructed and used for the continuous, in situ monitoring of cyanide concentrations in river water for 5 months, taking reading every 5 min, convincingly demonstrating the utility of our sensor. Although the sensitivity (mV/[CN-] of the sensor system tended to decrease over time, replacement of the gas-diffusion membrane restored the sensitivity to its initial level. In all cases, calibration curves yielded correlation coefficients ranging from r 2 = 0.991−1.00.

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A fluorescence flow injection method for the quantitation of cyanide: its application to the quantitation of bound cyanide in cassava using an immobilized linamarase bioreactor

Cited by 5 publications

References 18 publications

Reactions of Orthophthalaldehyde with Nucleophiles

Reactions of Orthophthalaldehyde with Nucleophiles

Separation of thiol and cyanide hydrolysis products of chemical warfare agents by capillary electrophoresis

Continuous in Situ Cyanide Monitoring Using a Highly Sensitive and Selective FIA System

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