The Amount of Ultraviolet Absorbance in a Synthetic Peptide is Directly Proportional to Its Number of Peptide Bonds

Becklin, Robert R.; Desiderio, Dominic M.

doi:10.1080/00032719508000037

Cited by 17 publications

(14 citation statements)

References 10 publications

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“…The given procedure has been successfully applied in quantitative analysis of peptides without aromatic side chains. 38 The UV/VIS chromatography analysis is given in Supporting Information ( Figure S15), whereas the product yields are given in Figure 2, Table 1).…”

Section: Analysis Ofmentioning

confidence: 99%

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Revisited Mechanism of Reaction between a Model Lysine Amino Acid Side Chain and 4-Hydroxynonenal in Different Solvent Environments

et al. 2018

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We revisit the reaction mechanism of reaction between model lysine side chain and reactive aldehyde 4-hydroxynonenal in different solvents with increasing water content. We show by model organic reactions and qualitative spectrometric analysis that non-polar pyrrole adduct is dominantly formed in non-aqueous solvents dichloromethane and acetonitrile. On the other hand, in aqueous acetonitrile and neat water, other polar products are also isolated including Michael adducts, hemiacetal adducts and pyridinium salt adducts, at the same time decreasing the ratio of non-polar products vs polar products. The experiments are supported by detailed quantum chemical calculations of the reaction mechanism with different computational setups showing that the pyrrole adduct is the most thermodynamically stable product compared to Michael adducts and hemiacetal adducts and also indicating that water molecules released along the reaction pathway are catalyzing reaction steps involving proton transfer. Finally, we also identify the mechanism of the pyridinium salt adduct which is formed only in aqueous solutions.

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Section: Analysis Ofmentioning

confidence: 99%

“…51,52 Experimental Details -400 nm, whereas the wavelength of 200 nm was selected for the analysis. 38 The NMR spectra (in CDCl3 at RT) were measured on a Bruker AV 600 spectrometer (Bruker BioSpin GmbH., Rheinstetten, Germany).…”

Section: Pyridine Salt Adduct Formationmentioning

confidence: 99%

Revisited Mechanism of Reaction between a Model Lysine Amino Acid Side Chain and 4-Hydroxynonenal in Different Solvent Environments

et al. 2018

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“…So, small peptides can be generally detected by UV-detection of their peptide bond(s) within the range from 205-230 nm (Koller & Eckert, 1997). However, peptides such as the tri-peptides IPP and VPP are difficult to detect, because the amount of UV light absorbed is directly related to the number of peptide bonds (Becklin & Desiderio, 1995) and, the mass spectrometric identification of native di-and tri-peptides is also challenging (Schmelzer, Schöps, Ulbrich-Hofmann, Neubert, & Raith, 2004). The situation for the detection of peptides can be improved when derivatisation procedures are taken into account (Careri & Mangia, 2003).…”

Section: Introductionmentioning

confidence: 99%

Quantification of dabsylated di- and tri-peptides in fermented milk

et al. 2012

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“…This demonstrates that low pH was necessary to protonate the analytes so that they could be separated as cations. Consequently, a stronger volatile acid, TFA, which had been used as acid to adjust pH for the separation of some peptides in capillary electrophoresis [32], was chosen for further study. Volatile TEA, which was expected to decrease the interaction between the cationic analytes and the capillary wall at low pH, thus increas- ing separation efficiency and improving separation, was selected as buffer cation.…”

Section: Scoutingmentioning

confidence: 99%

Separation of lidocaine and its metabolites by capillary electrophoresis using volatile aqueous and nonaqueous electrolyte systems

et al. 2001

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The separation of the basic drug lidocaine and six of its metabolites has been investigated both by using volatile aqueous electrolyte system, at low pH and by employing non-aqueous electrolyte systems. In aqueous systems, the best separation of the compounds under the investigated conditions was achieved by using the electrolyte 60 mM trifluoroacetic acid (TFA)/triethylamine (TEA) at pH 2.5 containing 15% methanol. With this electrolyte, all seven compounds were well separated with high efficiency and migration time repeatability. The separations with bare fused-silica capillaries and polyacrylamide-coated capillaries were compared with higher separation efficiency with the latter. On the other hand, near baseline separation of all the seven compounds was also obtained by employing the non-aqueous electrolyte, 40 mM ammonium acetate in methanol and TFA (99:1, v/v), with comparable migration time repeatability but lower separation efficiency relative to the aqueous system.

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The Amount of Ultraviolet Absorbance in a Synthetic Peptide is Directly Proportional to Its Number of Peptide Bonds

Cited by 17 publications

References 10 publications

Revisited Mechanism of Reaction between a Model Lysine Amino Acid Side Chain and 4-Hydroxynonenal in Different Solvent Environments

Revisited Mechanism of Reaction between a Model Lysine Amino Acid Side Chain and 4-Hydroxynonenal in Different Solvent Environments

Quantification of dabsylated di- and tri-peptides in fermented milk

Separation of lidocaine and its metabolites by capillary electrophoresis using volatile aqueous and nonaqueous electrolyte systems

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