N-Bromosuccinimide assisted oxidation of tripeptides and their amino acid analogs: Synthesis, kinetics, and product studies

Kumara, M. N.; Gowda, N. S. Linge; Mantelingu, Kempegowda; Rangappa, Kanchugara Koppal S.

doi:10.1016/j.molcata.2009.05.024

Cited by 11 publications

(8 citation statements)

References 19 publications

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“…Many kinetic and mechanistic studies were carried out by different researchers for different oxidation reactions by using NBS as the oxidizing agent. For example, kinetic and mechanistic studies on the oxidation of cycloheptanol in acid solution, oxidation of digol, − oxidation of amino acids and peptides, − oxidation of various sugars, − and oxidation of different acids − such as ethylenediaminetetraacetic acid, , aspartic acid, malic acid, and citric acid were reported. Similar studies were undertaken for the oxidation of allyl alcohol, − benzyl ethers, benzhydrols, amines and amino alcohols, − glycols, , cardiotoxin II,nitrones and N ,α-diphenylnitrones, , dibenzyl sulfoxide, and substituted aromatic acetals .…”

Section: Oxidation Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Oxidation Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…The reaction of angiotensin I with NaOCl leads to the formation of chloramine 6), 16), 17) at the N-terminal, followed by hydrolysis to the carbonyl group. 18) The carbonyl group is generated as 1,2-diketone (compound A, in Fig. 5); thereafter, the ketonization at the N-terminal side induces a reaction with DNPH (corresponding to m/z 1475.7, peak 4), and a partial decarboxylation, yielding the product giving peak 2 (corresponding to m/z 1431.7) in Fig.…”

Section: Carbonylated Angiotensin I Modified By 12 C 6 -mentioning

confidence: 99%

Protein Carbonylation Detected with Light and Heavy Isotope-Labeled 2,4-Dinitrophenylhydrazine by Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry

Kinumi

Osaka

Hayashi

et al. 2009

J. Mass Spectrom. Soc. Jpn.

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Oxidation of proteins leads to carbonylationῌthe formation of aldehydes or ketonesῌat the amino acid side chain and/or the terminal amino groups. Carbonylated proteins have been conventionally detected by UV absorption spectrometry of the stable adduct with 2,4-dinitrophenylhydrazine (DNPH). However, this routine method is limited to detection of the total carbonyl content and does not provide structural information. We developed an isotope-dilution method for the specific detection of carbonylated proteins using 12 C6-DNPH and 13 C6-DNPH. This method has the following steps: the oxidized protein or peptide is divided into two parts, and these parts are independently labeled with 12 C6-DNPH and 13 C6-DNPH; the mixtures of these two labeled solutions are subsequently measured with matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry. The carbonylated peptide was found by searching for a doublet peak having a mass di#erence of 6 Da. We examined oxidized angiotensin I and oxidized lysozyme prepared by treatment with NaOCl. The oxidized angiotensin I showed four pairs of doublet peaks in the MALDI-TOF mass spectrum. The structure was determined by tandem mass spectrometry. In the case of tryptic digest of the oxidized lysozyme, two carbonylated products could be easily identified even in a complex mixture. The use of 13 C6-DNPH provides rapid and accurate detection of carbonylated peptides even in complex mixtures.

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“…We also reported reaction mechanism and the comparative studies on the kinetics of oxidation of AAs and peptides (di, tri, and tetra) by NBS [8][9][10]. In all the above studies, an apparent correlation was observed between the rate of oxidation and the hydrophobicity of peptide sequences.…”

Section: Introductionmentioning

confidence: 99%

Oxidation of L‐amino acids by metal ion (Mn³⁺) in sulfuric acid medium: Effect of nucleophilicity and hydrophobicity on reaction rate

Kumara

Mantelingu

Bhadregowda

et al. 2011

Int J of Chemical Kinetics

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The kinetics of oxidation of L-amino acids (AAs) glycine(1a), alanine(1b), valine(1c), isoleucine(1d), leucine(1e), proline(1f), and phenylalanine(1g) by a transition metal ion (Mn 3+ ) was studied in the presence of sulfuric acid medium at 26 • C by a spectrophotometrical (λ max = 500 nm) method. In all cases, the kinetics of reactions was of first-order with respect to each [AA] and [Mn 3+ ]. Increased [H + ], [Mn 2+ ] (the reduction product of Mn 3+ ), sulfate, and chloride had no effect on the reaction rate. However, the reaction rate increased with increased dielectric constant of the medium. Oxidation rate increased for 1a-g and an apparent correlation was observed between the rate of oxidation and nucleophilicty of AAs except for 1a and 1g. The reaction rate also linearly depended on the hydrophobicity of AAs except for 1f and 1g. The thermodynamic parameters for AA-metal ion complex formation and activation parameters for the rate-limiting steps have been evaluated. Analysis of the oxidation products indicated that the AAs underwent oxidative deamination and decarboxylation to form corresponding aldehydes. Based on these data, plausible mechanisms involved in the oxidation of AAs are proposed. C

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N-Bromosuccinimide assisted oxidation of tripeptides and their amino acid analogs: Synthesis, kinetics, and product studies

Cited by 11 publications

References 19 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Protein Carbonylation Detected with Light and Heavy Isotope-Labeled 2,4-Dinitrophenylhydrazine by Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry

Oxidation of L‐amino acids by metal ion (Mn³⁺) in sulfuric acid medium: Effect of nucleophilicity and hydrophobicity on reaction rate

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N-Bromosuccinimide assisted oxidation of tripeptides and their amino acid analogs: Synthesis, kinetics, and product studies

Cited by 11 publications

References 19 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Protein Carbonylation Detected with Light and Heavy Isotope-Labeled 2,4-Dinitrophenylhydrazine by Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry

Oxidation of L‐amino acids by metal ion (Mn3+) in sulfuric acid medium: Effect of nucleophilicity and hydrophobicity on reaction rate

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Oxidation of L‐amino acids by metal ion (Mn³⁺) in sulfuric acid medium: Effect of nucleophilicity and hydrophobicity on reaction rate