The kinetics of diastereomeric amino acids with <i>o</i>‐phthaldialdehyde

Meyer, Marc; Meyer, Veronika R.; Ramseyer, S. F.

doi:10.1002/chir.530030611

Cited by 10 publications

(9 citation statements)

References 15 publications

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“…Using the reagent containing OPA and 2-ME it was possible to distinguish epimers, diastereoisomeric amino acids, based on differences in the rates of reactions yielding the fluorescent product …”

Section: 14 Structures Of Amino Acids and Aminesmentioning

confidence: 99%

“…Under such conditions the reaction resulting in formation of the adduct proceeds rapidly and the highest concentration of the fluorescent adduct is reached within minutes or their fractions. Therefore, studies of the initial stage of this reaction were carried out using stop-flow technique. ,,, To follow the reaction, more recently ,− special spectrophotometric techniques enabling rapid measurement of absorbance instead of following the fluorescence have been introduced.…”

Section: 4 Kinetics Of the Formation Of The Primary Productmentioning

confidence: 99%

“…Detectors based on measurement of fluorescence intensity of the primary product of the reaction between OPA, thiol, and amino compounds have been widely used in chromatographic and flow-injection analysis of mixtures of amino acids and other primary amines (cf. for examples refs , , , , , and 125; due to the large number of publications dealing with applications of such techniques, these references should be considered only as examples). Both precolumn 125,126 and postcolumn derivatization were used.…”

Section: 7 Techniques Usedmentioning

confidence: 99%

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Reactions of Orthophthalaldehyde with Nucleophiles

Zuman

2004

Chem. Rev.

127

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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: 14 Structures Of Amino Acids and Aminesmentioning

confidence: 99%

Section: 4 Kinetics Of the Formation Of The Primary Productmentioning

confidence: 99%

Section: 7 Techniques Usedmentioning

confidence: 99%

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Reactions of Orthophthalaldehyde with Nucleophiles

Zuman

2004

Chem. Rev.

127

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“…Kinetic data on the OPA reaction of the common amino acids have been published by Svedas et al [24] and Meyer et al [25]. It was shown that the reaction is second order in the amino acid and OPA concentrations, with rate constants between 20 and 100 mol-lls -1 for most amino acids.…”

Section: Kinetics Of the Opa Reactionmentioning

confidence: 98%

Post-column reaction system for fluorescence detection in capillary electrophoresis

Zhu

Kok

1995

Journal of Chromatography A

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A system for post-column derivatization in capillary electrophoresis has been developed and evaluated. In this system, reagent is added through a porous tube connecting the separation capillary with a reactor capillary. The reagent solution is driven by a regulated air pressure applied on the separation capillary inlet and the reagent vessel simultaneously. The system has been applied for the fluorescence detection of amino acids using o-phthalaldehyde as reagent. The reactor capillary geometry and flow-rates were optimized with respect to sensitivity and separation efficiency on the basis of measured reaction rate constants. A ten-fold increase in sensitivity could be obtained by using "bubble-cell" capillaries instead of normal fused-silica capillaries for detection.Amino acids were separated in a pH 9.7 borate buffer. Plate numbers in the order of 100 000 to 150 000 were obtained. Detection limits were typically between 2.10 -6 and 4.10 -6 mol 1-1, or 0.05 to 0. l pmo1 injected. The method was applied to the determination of free amino acids in urine samples.

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“…Measurements of the intensity of fluorescence of the species resulting in the reaction of OPA in the presence of a thiol with AAs has been widely used in chromatographic and flow-injection analyses as examples of the large number of reported applications can attest (Meyer et al 1991;Svedas et al 1978;Qureshi 1987;Ashman and Bosserhoff 1985;Joseph and Davies 1983;Allison et al 1984;Oka et al 1984;Kim 1987;Forster and Marsden 2001). In chromatography, the reaction can be used either in the pre-column or post-column derivatization.…”

mentioning

confidence: 99%

Reactions of Orthophthalaldehyde and Related Compounds with Amino Acids

Zuman¹

2005

Analytical Letters

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Reaction of orthophthalaldehyde with thiols and of the product of this reaction with amino acids is commonly used for determination of amino acids. This reaction is often utilized in pre-column and post-column derivatization in chromatography and forms the basis of procedures applied in commercial amino acid analyzers. The product of this reaction is known to be an isoindole derivative, but the reaction paths of its formation are not understood. Better knowledge of chemical processes involved seems essential for development of more reliable procedures for determination of amino acids.Determination of amino acids (AAs) plays an important role in the solution of various problems in biochemistry and biology. In the past, a color reaction with ninhydrin (Cheronis 1954) has been used for detection of AAs, but its application for quantitative determination of AAs suffered from limited sensitivity.In the search for a reagent that would enable determination of AAs at a lower concentration level, Roth (1971) investigated reactions of AAs with carbonyl compounds that would result in formation of a fluorescent species. The starting point of his study was a report (Hillmann 1943) that o-diacetylbenzene yielded a fluorescent species in the presence of proteins. Roth carried out the reactions of o-diacetylbenzene with AAs in a

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The kinetics of diastereomeric amino acids with o‐phthaldialdehyde

Cited by 10 publications

References 15 publications

Reactions of Orthophthalaldehyde with Nucleophiles

Reactions of Orthophthalaldehyde with Nucleophiles

Post-column reaction system for fluorescence detection in capillary electrophoresis

Reactions of Orthophthalaldehyde and Related Compounds with Amino Acids

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