2017
DOI: 10.5702/massspectrometry.a0059
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A Facile Method for Preferential Modification of the N-Terminal Amino Group of Peptides Using Triazine-Based Coupling Reagents

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Cited by 6 publications
(4 citation statements)
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“…The Nterminus is also a good target, as there is a difference in its conjugate acid's pKa, as well as nucleophilicity, when comparing it to the sidechain amine on lysine [17] . While there are methods that allow for the selective modification of the N-terminal amine over lysine amines, most of them rely on permanently modifying the N-terminus, such as creating a new amide bond [18] or converting the N-terminal amino acid into an aldehyde [19] . It is also possible to use the C-terminus as a handle for peptide purification, however, due to the similarities between the side chain carboxylic acids of Asp and Glu and the C-terminus this is a less attractive option (the pKa of these three range from 3.3-4.2) [20] .…”
Section: Resultsmentioning
confidence: 99%
“…The Nterminus is also a good target, as there is a difference in its conjugate acid's pKa, as well as nucleophilicity, when comparing it to the sidechain amine on lysine [17] . While there are methods that allow for the selective modification of the N-terminal amine over lysine amines, most of them rely on permanently modifying the N-terminus, such as creating a new amide bond [18] or converting the N-terminal amino acid into an aldehyde [19] . It is also possible to use the C-terminus as a handle for peptide purification, however, due to the similarities between the side chain carboxylic acids of Asp and Glu and the C-terminus this is a less attractive option (the pKa of these three range from 3.3-4.2) [20] .…”
Section: Resultsmentioning
confidence: 99%
“…The Nterminus is also a good target, as there is a difference in its conjugate acid's pKa, as well as nucleophilicity, when comparing it to the sidechain amine on lysine [17] . While there are methods that allow for the selective modification of the N-terminal amine over lysine amines, most of them rely on permanently modifying the N-terminus, such as creating a new amide bond [18] or converting the N-terminal amino acid into an aldehyde [19] . It is also possible to use the C-terminus as a handle for peptide purification, however, due to the similarities between the side chain carboxylic acids of Asp and Glu and the C-terminus this is a less attractive option (the pKa of these three range from 3.3-4.2) [20] .…”
Section: Resultsmentioning
confidence: 99%
“…30 Acylation of amines is a commonly used strategy to functionalize, for example, biopharmaceuticals, and often lysine residues are modified in this way, but only a few approaches for N-terminal acylation have been reported, and more of these are either not very selective and efficient or have only been tested on simple peptide substrates. 31,32 N-Hydroxysuccinimide (NHS) is one of the most used reagents to form activated esters used for the acylation of amines in peptide chemistry. 33 amines and ε-lysine amines, even at a neutral pH, as well as with hydroxyl groups on tyrosine, threonine, and serine to form O-acylated-byproducts, 34−36 and therefore, are a poor choice of reagent for selective N-terminal acylation.…”
Section: ■ Introductionmentioning
confidence: 99%
“…Acylation of amines is a commonly used strategy to functionalize, for example, biopharmaceuticals, and often lysine residues are modified in this way, but only a few approaches for N -terminal acylation have been reported, and more of these are either not very selective and efficient or have only been tested on simple peptide substrates. , …”
Section: Introductionmentioning
confidence: 99%