The isolation of a new hypotensive peptide, neurotensin, from bovine hypothalami.

Structure of the porcine LH- and FSH-releasing hormone. I. The proposed amino acid sequence

Publisher Summary The methods of amino-terminal analysis and sequence determination based on dansyl chloride have application because of the ease with which one can study minute amounts of peptides and proteins. Dansyl chloride is reactive toward a variety of bases. In sequence analysis, the most important of these are the primary and secondary amines present as the terminal amino groups of peptides and proteins. Compared with most other end-group reagents, dansyl chloride is rather susceptible to hydrolysis by water and hydroxyl ions. Many substances greatly quench the fluorescence of dansyl amino acids, including water, acids, and pyridine. Any dansyl chloride that remains is subsequently broken down during the acid hydrolysis; no labeling of newly exposed amino groups occurs under these conditions. The very simple procedure recommended for peptides is usually unsuitable for proteins, mainly because of a need to use much more dansyl chloride, and larger volumes.

[8] End-group analysis using dansyl chloride.

An extracellular protease of Staphylococcus aureus, strain V8, previously shown to cleave specifically the peptide bonds on the carboxyl-terminal side of either aspartate or glutamate residues in phosphate buffer (pH 7.8) hydrolyzes only glutamoyl bonds in either ammonium bicarbonate (pH 7.8) or ammonium acetate (pH 4.0). Of all aspartoyl bonds tested, only the Asp-Gly linkage is cleaved at a detectable rate. The staphylococcal protease hydrolyzes all of the seventeen different glutamoyl bonds studied, although those involving hydrophobic aminoacid residues with bulky side chains are cleaved at a lower rate.

https://www.pnas.org/content/pnas/69/12/3506.full.pdf

Staphylococcal Protease: A Proteolytic Enzyme Specific for Glutamoyl Bonds

http://www.jbc.org/content/247/10/3242.full.pdf

Amino-terminal Sequence Analysis of Proteins Purified on a Nanomole Scale by Gel Electrophoresis

The reaction rates between dansyl chloride and water, amino acids or peptides are studied as a function of pH and temperature. The rate of hydrolysis of dansyl chloride is constant and low up to pH 9.5 and above this pH it increases rapidly. The various reactive groups of amino acids and peptides react with dansyl chloride in their unprotonated form. It is shown that a compromise for optima conditions of dansylation (pH and temperature) may be found, taking into account the rate of hydrolysis and the pK of the group to be dansylated.

A complete chromatographic separation on Silica gel G thin layer plates of dansyl amino acids is proposed using 4 solvents. The quantitative recovery of the separated derivatives is described.

The study of the acid hydrolysis of dansylated proteins shows that the release of the dansyl derivatives from the peptide chain is faster than that of free amino acids; it also shows that the destruction of dansyl amino acids occurs rather rapidly. Therefore a hydrolysis time of 4 hours (110°) is suggested, except in the special cases of the release of dansyl valine, dansyl leucine or dansyl isoleucine which needs 18 hours of hydrolysis.

For quantitative estimation of each dansyl derivative a correction factor is given, taking into account the loss during hydrolysis, the recovery from the plates and the individual fluorescence of any dansyl derivative as compared to the fluorescence of a reference compound.

The general conditions described in this work require 1 nmole of material for qualitative determination of the N-terminal amino acids, and 5–10 nmoles for their quantitative estimation.

Some examples (α-chymotrypsin, trypsinogen, ribonuclease, lysozyme, aspartokinase and triose phosphate dehydrogenase) illustrate the efficiency of the method.

https://febs.onlinelibrary.wiley.com/doi/pdf/10.1111/j.1432-1033.1969.tb19632.x

Study of the dansylation reaction of amino acids, peptides and proteins

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Study of the dansylation reaction of amino acids, peptides and proteins