A colorimetric assay for carbodiimides commonly used in peptide synthesis and carboxyl group modification

Jacobson, Bernard; Fairman, Kenneth R.

doi:10.1016/0003-2697(80)90125-6

Cited by 15 publications

(11 citation statements)

References 7 publications

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“…Hydration of water-soluble carbodiimides Initial carbodiimide concentration was 0.2 M. Hydration was studied in buffer A or in buffer A containing 5 10-4 M (per monomer) dpA, d(AAAA) or d(AAAAp). Carbodiimide conversion was assayed spectrophotometrically using a quantitative color reaction for the -N=C=Ngroup [3,7]. Chemical and enzymatic ligation of oligonucleotides Nucleotide concentration of duplexes I and H was about 10-3 M (per monomer); 5'-32p labelled oligonucleotides were added in a 1.5-fold deficiency as compared to the unlabelled ones.…”

Section: Preparation Of Synthetic Oligomersmentioning

confidence: 99%

Structural and kinetic aspects of chemical reactions in DNA duplexes. Information on DNA local structure obtained from chemical ligation data

et al. 1991

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Chemical ligation of oligonucleotides in double-stranded helices has been considered in its structural-kinetic aspect. A study was made of (i) two series of DNA duplexes with various arrangements of reacting groups in the ligation junction induced by mispairing or by alteration of furanose structure (the replacement of dT unit with rU, aU, IU, xU, dxT ones) and of (ii) eight synthetic water-soluble carbodiimides with different substituents at N1 and N3 atoms. We assumed that some information on the local structure of modified sites in the duplex can be obtained from kinetic parameters of oligonucleotide coupling reaction. The ratio of kinetic constants k3/(k2 + k3) for productive and nonproductive decomposition of the activated phosphomonoester derivative apparently reflects the reaction site structure: for a given duplex this parameter is virtually independent of the condensing agent composition. Based on the analysis of the chemical ligation kinetics a suggestion has been made about the conformation of some modified units in the double helix.

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Section: Preparation Of Synthetic Oligomersmentioning

confidence: 99%

Structural and kinetic aspects of chemical reactions in DNA duplexes. Information on DNA local structure obtained from chemical ligation data

et al. 1991

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“…Carbodiimide (III) (43.1 mg, 0.225 mmol or 86.3 mg, 0.45 mmol) was added to the vigorously stirred reaction mixture at 20-22°C, and pH of the reaction mixture was kept within the interval from 4.7 to 4.8 by titration with 0.1 N HCl. The consumption of EDC was determined according to the method described in [19]. After 2 h, the reaction mixture was neutralized with 0.1 N NaOH (to pH 7), diluted with the saturated solution of NaCl (4-5 ml) and ethanol (120-130 ml), and cooled to 0°C.…”

Section: Modification Of Ha By Amino Acids (Iia)-(iid)mentioning

confidence: 99%

Modification of hyaluronic acid with aromatic amino acids

et al. 2005

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Hyaluronic acid was modified with aromatic amino acids (5-aminosalicylic, 4-aminosalicylic, anthranilic, and p -aminobenzoic) in the presence of 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide. The modified glycans contained 9-43% of arylamide groups and 10-33% of isoureidocarbonyl groups depending on the nature of the amino acid. Reduction with sodium borohydride allowed the conversion of isoureidocarbonyl groups into hydroxymethyl groups.

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“…Also, a spectrophotometric method by flow injection analysis (FIA) has been developed for the determination of EDC·HCl in aqueous samples, 22 which is measured in a short time and with a simple procedure. However, its sensitivity was not good: the limit of quantification (LOQ) was 0.1% (5 ¥ 10 -5 M).…”

Section: Introductionmentioning

confidence: 99%

“…Some other spectrophotometric methods have been reported, whereas their analytical performance is not practical, which requires several hours for an EDC·HCl measurement. [22][23][24] It is caused by the stable ring structure of EDC·HCl itself in aquatic media, and it takes much time to react. In our previous work, 25 a simple and rapid FIA technique was developed for EDC·HCl determination by using an effective reaction with pyridine and ethylenediamine in acidic solution (0.1 M HCl).…”

Section: Introductionmentioning

confidence: 99%

Determination of 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide Hydrochloride by Flow-Injection Analysis Based on a Specific Condensation Reaction between Malonic Acid and Ethylenediamine

et al. 2009

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A sensitive and rapid flow-injection analysis was developed for the determination of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl), which was used for the formation of amide (peptide) and esters as a dehydration or condensation reagent. The EDC·HCl could be determined by the flow-injection analysis based on a specific condensation reaction between malonic acid and ethylenediamine in aquatic media. The reaction was accelerated at 60˚C, and the absorbance of the product was detected at 262 nm. The calibration graph of EDC·HCl showed good linearity in the range from 0 to 0.1% (0 to 0.0005 M), whose regression equation was y = 1.52 ¥ 10 9 x (y, peak area; x, % concentration of EDC·HCl). The proposed method allowed high-throughput analysis; the sample throughput was 12 samples per hour. The limit of detection (LOD) and the relative standard deviation (RSD) were 2 ¥ 10 -6 M and 1.0%, respectively. This reaction is proceeded in aqueous solution and specific for EDC·HCl.

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A colorimetric assay for carbodiimides commonly used in peptide synthesis and carboxyl group modification

Cited by 15 publications

References 7 publications

Structural and kinetic aspects of chemical reactions in DNA duplexes. Information on DNA local structure obtained from chemical ligation data

Structural and kinetic aspects of chemical reactions in DNA duplexes. Information on DNA local structure obtained from chemical ligation data

Modification of hyaluronic acid with aromatic amino acids

Determination of 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide Hydrochloride by Flow-Injection Analysis Based on a Specific Condensation Reaction between Malonic Acid and Ethylenediamine

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