Electrochemistry of the carbon–nitrogen double bond

Lund, Henning

doi:10.1002/9780470771204.ch11

Cited by 16 publications

(6 citation statements)

References 105 publications

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“…We take advantage of the fact that the electrochemical reduction of the imine is markedly easier and produces the racemic 0.5 L-alanine + 0.5 D-alanine. Therefore, the cathode potential can be tuned so as to achieve a selective reduction (Anne et al, 1994;Jeffery and Meisters, 1978;Lund, 1970).…”

Section: Introductionmentioning

confidence: 99%

Can the combination of electrochemical regeneration of NAD+, selectivity of L-?-amino-acid dehydrogenase, and reductive amination of ?-keto-acid be applied to the inversion of configuration of a L-?-amino-acid?

Anne

Bourdillon

Daninos

et al. 1999

Biotechnol. Bioeng.

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Section: Introductionmentioning

confidence: 99%

Can the combination of electrochemical regeneration of NAD+, selectivity of L-?-amino-acid dehydrogenase, and reductive amination of ?-keto-acid be applied to the inversion of configuration of a L-?-amino-acid?

Anne

Bourdillon

Daninos

et al. 1999

Biotechnol. Bioeng.

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“…Anodic peak may be due to oxidation of secondary amino group in the irreversible and diffusion controlled oxidation [29]. Cathodic peak may be due to reduction Nitrile group involves four protons and four-electron transfer reaction or reduction of Carbonyl group, which involves 2 electrons and 2 protons involves [30,31] or reduction Sulphonyl group, which involves 6 electron and 6 protons [32][33][34][35][36][37][38]. Further to study the electrochemical behavior of Bicalutamide, only reduction property is selected, CV is carried out with the potential sweep rate in the range of 25 to 300 mV s -1 and Potential ranges from -0.2V to -2.2V and well defined cathodic peak obtained in between -1.0555V to -1.2189 V. Fig -(2) shows Cyclic Votammogram of Bicalutamide 1x10 -4 M in DMF and Tetra Butyl ammonium per chlorate as supporting electrolyte.…”

Section: Results and Discussion 31 Electrochemical Behavior Of Bicmentioning

confidence: 99%

Electrochemical behavior and differential pulse voltametric determination of an antineoplastic drug bicalutamide and pharmaceuticals formulations using glassy carbon electrode

Raghu¹,

Chandrasekar²,

KR³

2010

Int J of Chem Res

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The redox characteristics of the drug Bicalutamide at a glassy-carbon electrode (GCE) was investigated for the first time in aqueous media by differential-pulse voltammetry (DPV) and cyclic voltammetry (CV). In Britton-Robinson (BR) buffer of pH 2.0-10.0, an irreversible and diffusion-controlled reduction voltagram were developed. The dependence of the CV response of the developed cathodic peak on the sweep rate (ν) and on depolarizer concentration was typical electrode-coupled chemical reaction mechanism (EC) in which an irreversible reaction is interposed between the charges. In BR buffer of pH 6 -7, a well defined cathodic peak was developed and the plot of peak current height of the DPV against Bicalutamide concentration at this peak potential was linear in the range 1×10 −8 -2.6 ×10 −5 M with lower limits of detection (LOD) and quantization (LOQ) of 8 x 10 -8 M and 1 ×10 −7 M, with good selectivity and sensitivity. A relative standard deviation (RSD) for Bicalutamide at a concentration of 4.5×10 −5 M was 2.48% (n=6). The proposed method was successfully applied to Bicalutamide determination in pharmaceutical samples and results are very good correlations with previously reported methods.

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“…Amidines, the nitrogen analogs of carboxylic acids and esters [16], possess a double bond (-C=N-) which is not reduced by sodium cyanoborohydride [17]. Indeed, in attempts to reduce the crosslinked peptide with sodium cyan~boro[~H]hydride at pH 6.0 in methanol, no radioactivity was incorporated.…”

Section: Discussionmentioning

confidence: 99%

Paracatalytic self‐inactivation of fructose‐1,6‐bisphosphate aldolase

Gupta¹,

Hollenstein²,

Kochhar³

et al. 1993

European Journal of Biochemistry

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Oxidation of enzyme‐substrate carbanion intermediates by extrinsic oxidants may result in irreversible paracatalytic inactivation of certain enzymes. In paracatalytically modified fructose‐1,6‐bisphosphate aldolase from rabbit muscle the polypeptide chain had been found to be crosslinked at active‐site Lys229 (Schiff base forming with substrate) and Lys146 by a phosphorylated three‐carbon moiety [Lubini, D. G. E. and Christen, P. (1979) Proc. Natl Acad. Sci. USA 76, 2527–2531]. In the present study, the structure of this crosslink was elucidated by instrumental analysis. Aldolase was paracatalytically modified in the presence of fructose 1,6‐bisphosphate and hexacyanoferrate(III). The completely inactivated enzyme was digested with pronase. The crosslinked peptide was isolated by gel filtration and reverse‐phase HPLC. Mass spectroscopy, 1H‐ and 13C‐NMR showed that a derivative of dihydroxyacetone phosphate forms an amidine with the ɛ‐amino groups of the two lysine residues:

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Electrochemistry of the carbon–nitrogen double bond

Cited by 16 publications

References 105 publications

Can the combination of electrochemical regeneration of NAD+, selectivity of L-?-amino-acid dehydrogenase, and reductive amination of ?-keto-acid be applied to the inversion of configuration of a L-?-amino-acid?

Can the combination of electrochemical regeneration of NAD+, selectivity of L-?-amino-acid dehydrogenase, and reductive amination of ?-keto-acid be applied to the inversion of configuration of a L-?-amino-acid?

Electrochemical behavior and differential pulse voltametric determination of an antineoplastic drug bicalutamide and pharmaceuticals formulations using glassy carbon electrode

Paracatalytic self‐inactivation of fructose‐1,6‐bisphosphate aldolase

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