A new strategy for synthesis of polymeric supports with triazene linkers

Łaźny, Ryszard; Nodzewska, Aneta; Kłosowski, Piotr

doi:10.1016/j.tet.2003.10.091

Cited by 23 publications

(11 citation statements)

References 30 publications

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“…We felt that this could be achieved by carrying out STaR directly on a solid support. Toward this end, arene‐diazonium‐ion‐functionalized resin was synthesized in two steps from 5‐amino‐2‐chloro benzylalcohol (Supplementary Figure 17) [46, 47] . The arene‐diazonium‐ion‐functionalized resin was incubated with mixture of peptides AKmeF, SVF, NAF, and RAF containing primary amines and other reactive side chains for 16 h followed by the extensive washing of beads with water and various organic solvents, such as ACN, DMF, MeOH, and DCM, to remove non‐covalently attached peptide fragments.…”

Section: Resultsmentioning

confidence: 99%

“…Toward this end, arene-diazoniumion-functionalized resin was synthesized in two steps from 5-amino-2-chloro benzylalcohol (Supplementary Figure 17). [46,47] Thea rene-diazonium-ion-functionalized resin was incubated with mixture of peptides AKmeF,S VF,N AF, and RAF containing primary amines and other reactive side chains for 16 hf ollowed by the extensive washing of beads with water and various organic solvents,such as ACN, DMF, MeOH, and DCM, to remove non-covalently attached peptide fragments.T he trapped peptides were released from the resin under mild acidic conditions using 10 %TFA/DCM for 10 min (Supplementary Figure 18). High mass intensity of the unmodified monomethyl lysine peptide AKmeF was observed after the cleavage from the resin without any further purification.…”

Section: Angewandte Chemiementioning

confidence: 99%

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Selective Triazenation Reaction (STaR) of Secondary Amines for Tagging Monomethyl Lysine Post‐Translational Modifications

et al. 2021

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Lysine monomethylation (Kme) is an impactful post‐translational modification (PTM) responsible for regulating biological processes and implicated in diseases, thus there is great interest in identifying these methylation marks globally. However, the progress in this area has been challenging because the addition of a small methyl group on lysine leads to negligible change in the bulk, charge, and hydrophobicity. Herein, we report an empowering chemical technology selective triazenation reaction, which we term “STaR”, of secondary amines using arene diazonium salts to achieve highly selective, rapid, and robust tagging of Kme peptides from a complex mixture under biocompatible conditions. Although the resulting triazene‐linkage with Kme is stable, we highlight the efficient decoupling of the triazene‐conjugate to afford unmodified starting components under mild conditions when desired. Our work establishes a unique chemoselective, traceless bioconjugation strategy for the selective enrichment of Kme PTMs.

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Section: Resultsmentioning

confidence: 99%

Section: Angewandte Chemiementioning

confidence: 99%

Selective Triazenation Reaction (STaR) of Secondary Amines for Tagging Monomethyl Lysine Post‐Translational Modifications

et al. 2021

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“…nortropine and 4-piperidinole), and as amine scavengers was demonstrated. 12 The application of biotransformations in solid phase synthesis as an attractive alternative to chemical methodologies has been reported. The paper shows that accessibility can be improved for penicillin G amidase by introducing permanent charges into the polymer.…”

Section: Novel Resins and Linkersmentioning

confidence: 99%

Combinatorial Chemistry Online

Terrett

2004

Combinatorial Chemistry - an Online Journal

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“…It has been shown by us [12][13][14][15][16] and others [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34] that diazenylsubstituted aminestriazenescan serve as very valuable starting materials and intermediates. They are stable towards many bases, but can be cleaved under mild acidic conditions to release the free amine or amine-derivative in a simple manner.…”

Section: Introductionmentioning

confidence: 99%