Colorimetric Monitoring of Solid-Phase Aldehydes Using 2,4-Dinitrophenylhydrazine

Shannon, Simon K.; Bárány, George

doi:10.1021/cc034033x

Cited by 39 publications

(31 citation statements)

References 53 publications

(63 reference statements)

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“…[7] To accelerate the kinetics of the reductive amination, the solubility of the reagents was improved by adding MeOH (19 %) to the resin, and the resulting mixture was heated to 60 8C. After 16 h, the negative result to a test with chloranil was indicative of a complete, successful reaction.…”

Section: Resultsmentioning

confidence: 99%

“…Complete loading of propargylamine onto the DFPE resin was verified by a negative result of a test with DNPH. [7] Synthesis of CO 2 HÀSPOrT resin 2: A solution of succinic anhydride (575.4 mg, 57.5 mmol) in DMF (1.55 mL), pyridine (74 mL, 0.92 mmol), and 4-DMAP (28.1 mg, 0.23 mmol) were added to the resin-bound alkyne 1 (0.23 mmol) preswollen in DMF. The resulting mixture was shaken overnight at room temperature.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Solid‐Phase Organic Tagging Resins for Labeling Biomolecules by 1,3‐Dipolar Cycloaddition: Application to the Synthesis of a Fluorescent Non‐Peptidic Vasopressin Receptor Ligand

Bron¹,

Riché²,

Loison³

et al. 2008

Chemistry A European J

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Two novel solid-phase organic tagging (SPOrT) resins were synthesized to facilitate the labeling of peptides and small organic compounds with a fluorescent probe. Both resins were obtained from the commercially available backbone amide linker (BAL) resin. Following the solid-phase synthesis of model compounds, a tripeptide and benzazepine, the fluorescent probe derived from Lissamine Rhodamine B was incorporated through CuI-catalyzed 1,3-dipolar cycloaddition. Final cleavage in acidic media enabled access to both types of molecules in good yield with high purity. The SPOrT resin was successfully applied to the preparation of the first non-peptidic fluorescent compound with a nanomolar affinity for the human vasopressin V2 receptor (V2R) subtype. This molecule will find application in binding assays that use polarization or fluorescence resonance energy-transfer (FRET) techniques. The SPOrT resins are also well suited for other tags and the parallel synthesis of a fluorescently tagged library for protein screening.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Solid‐Phase Organic Tagging Resins for Labeling Biomolecules by 1,3‐Dipolar Cycloaddition: Application to the Synthesis of a Fluorescent Non‐Peptidic Vasopressin Receptor Ligand

Bron¹,

Riché²,

Loison³

et al. 2008

Chemistry A European J

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“…It has already been established that hydrazines react with carbonyl compounds to form hydrazones. [22][23][24] DNPH has previously been used to quantify protein carbonyl markers [25] and stereoisomers of low-molecular-weight aldehyde compounds [26] by HPLC analysis. In the current study, we developed a new and easier method to analyze periodate oxidation using DNPH assay spectrophometrically.…”

Section: Introductionmentioning

confidence: 99%

A UV-Vis Spectrophotometric Method for the Estimation of Aldehyde Groups in Periodate-Oxidized Polysaccharides Using2,4-Dinitrophenyl Hydrazine

Tummalapalli¹,

Gupta²

2015

Journal of Carbohydrate Chemistry

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In this study, efforts have been made to develop a simple approach to determine aldehyde content in periodate-oxidized polysaccharides. A UV-Vis analytical technique using 2,4-dinitrophenylhydrazine (DNPH) was employed to calculate the aldehyde content. When tested against compounds like acetaldehyde and formaldehyde with known aldehyde content, the DNPH method yielded accurate results. The DNPH assay was Analysis of Aldehydes in Polysaccharides by UV-Vis 339further utilized to analyze the aldehyde generation during periodate oxidation of pectin, a naturally occurring plant polysaccharide. It was found that the DNPH assay was sensitive even at low concentrations of aldehyde and yielded accurate results. Therefore, this method could be used to control and optimize reaction parameters during the periodate oxidation of polysaccharides.

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“…The completion of the reaction on the resin bead was monitored by infrared (IR) spectroscopy (attenuated total reflectance) showing new bands at approximately 1670 cm À1 (CQO stretch, amide) and 1600 cm À1 (CQO stretch, aldehyde). Additionally, the reaction was monitored colorimetrically with 2,4-dinitrophenylhydrazine (DNPH) in sulfuric acid giving dark orange-red beads for resin-bound aldehyde groups according to the procedure by Shannon et al 17 Subsequently, reductive amination between the FMPB aldehyde group and an alkyl amine allowed a C-terminal modification by an alkyl chain of choice (Scheme 1). The reductive amination was carried out by employing sodium cyanoborohydride (NaBH 3 CN) in N-methyl-2-pyrrolidone (NMP) under mild acidic conditions (5% acetic acid).…”

Section: Synthesis Of Polylysine Dendronsmentioning

confidence: 99%

Preparation and self-assembly of amphiphilic polylysine dendrons

et al. 2016

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a Herein, we present the synthesis of new amphiphilic polylysine dendrons with variable alkyl chain lengths (C1-C18) at the C-terminal. The dendrons were synthesized in moderate to quantitative yields by divergent solid-phase synthesis (SPS) employing an aldehyde linker. The self-assembling properties of the dendrons in aqueous solutions were studied by small angle neutron scattering (SANS) and dynamic light scattering (DLS). The self-assembling properties were influenced by the length of the alkyl chain and the generation number (Gn). Increasing the temperature and concentration did not have significant impact on the hydrodynamic diameter, but the self-assembling properties were influenced by the pH value. This demonstrated the need for positively charged amines in the head groups for the successful formation of controlled self-assemblies. Dendrons having alkyl chains below C8 did not self-assemble. Well-defined micellar structures observed with SANS were formed with alkyl chain lengths above C12.Large structures detected with DLS for dendrons with alkyl chain lengths above C12 are ascribed to intermicellar aggregates stabilized by hydrophobic and electrostatic forces in accordance with the observed pH effect. Finally, the cytotoxicity of the dendrons was evaluated in mouse fibroblast (NIH/3T3) and human embryonic kidney (HEK 293T) cells at 5, 10 and 20 mM concentrations. The dendrons showed low cytotoxicity, displaying cell viability well above 80%.

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Colorimetric Monitoring of Solid-Phase Aldehydes Using 2,4-Dinitrophenylhydrazine

Cited by 39 publications

References 53 publications

Solid‐Phase Organic Tagging Resins for Labeling Biomolecules by 1,3‐Dipolar Cycloaddition: Application to the Synthesis of a Fluorescent Non‐Peptidic Vasopressin Receptor Ligand

Solid‐Phase Organic Tagging Resins for Labeling Biomolecules by 1,3‐Dipolar Cycloaddition: Application to the Synthesis of a Fluorescent Non‐Peptidic Vasopressin Receptor Ligand

A UV-Vis Spectrophotometric Method for the Estimation of Aldehyde Groups in Periodate-Oxidized Polysaccharides Using2,4-Dinitrophenyl Hydrazine

Preparation and self-assembly of amphiphilic polylysine dendrons

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