Reactions of Orthophthalaldehyde with Nucleophiles

Abstract

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

Crystal structure of 2-tert-butyl-2,3-dihydro-1H-benzo[c]pyrrol-1-one

“…The reaction of OPA with aliphatic primary amines in aqueous solutions involves competition between the amines and water molecules as nucleophiles. Although water is a weaker nucleophile than primary amines, an enormous excess of water over primary amines may cause significant additional reactions, such as covalent hydration at the double bond of the carbonyl group and the following cyclization (Zuman, 2004) -see compounds (II) and (III) in Fig. 1.…”

A diverse structural behaviour of boronated ortho-phthalaldehydes: A crystal structure of 1,3-dihydro-1,3-dihydroxy-4-formylbenzo[c][2,1]oxaborole

“…More recently, OPA has been recognized as the potent antibacterial agent acting due to the reaction with aminoacids and proteins [4]. Furthermore, the method of determination of trace amounts of aminoacids is based on their reactions with OPA and its analogues yielding fluorescent isoindoles [5]. In our contribution we report about novel boronated analogues of OPA.…”

Analysis of PTH‐Cysteine by Adsorptive Stripping Square‐Wave Voltammetry

“…The absence of a strong fluorescence or UV-vis active group leads to the use of different derivative agents to get a chromophorecontained derivative product in order to increase sensitivity. Among the most commonly employed are o-phthalaldehyde [3,4], dansyl chloride (Dns-Cl) [5], phenylisothiocyanate [6 -7] and phanquinone [8] which have been reported as derivative reactives for different detection techniques. The use of capillary electrophoresis provides speed of analysis over HPLC without the use of gradient in addition to the lower solvent waste production.…”