19047-21-3Relevant articles and documents
Dialdehydes lead to exceptionally fast bioconjugations at neutral pH by virtue of a cyclic intermediate
Schmidt, Pascal,Zhou, Linna,Tishinov, Kiril,Zimmermann, Kaspar,Gillingham, Dennis
, p. 10928 - 10931 (2015)
One of the open challenges in chemical biology is to identify reactions that proceed with large rate constants at neutral pH values. As shown here, dialdehydes react with O-alkylhydroxylamines at rates of 500 M-1 s-1 at neutral pH va
METHOD FOR CONJUGATING MOLECULES
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Paragraph 0209-0210, (2016/08/17)
Methods of conjugating two molecules are disclosed herein in which a non-polymeric aliphatic dialdehyde or non-polymeric aromatic dialdehyde is reacted with a compound comprising an amine (NH2) moiety to form a stable product under mild conditions.
Tuning a three-component reaction for trapping kinase substrate complexes
Statsuk, Alexander V.,Maly, Dustin J.,Seeliger, Markus A.,Fabian, Miles A.,Biggs, William H.,et al.
supporting information; experimental part, p. 17568 - 17574 (2009/09/08)
The upstream protein kinases responsible for thousands of phosphorylation events in the phosphoproteome remain to be discovered. We developed a three-component chemical reaction which converts the transient noncovalent substrate-kinase complex into a covalently cross-linked product by utilizing a dialdehyde-based cross-linker, 1. Unfortunately, the reaction of 1 with a lysine in the kinase active site and an engineered cysteine on the substrate to form an isoindole cross-linked product could not be performed in the presence of competing cellular proteins due to nonspecific side reactions. In order to more selectively target the cross-linkerto protein kinases in cell lysates, we replaced the weak, kinase- bindi ng adenosine moiety of 1 with a potent protein kinase inhibitor scaffold. In addition, we replaced the o-phthaldialdehyde moiety in 1 with a less-reactive thiophene-2,3-dicarboxaldehyde moiety. The combination of these two structural modifications provides for cross-linking of a cysteine-containing substrate to its corresponding kinase in the presence of competing cellular proteins.
o-naphthalenedicarboxaldehyde derivative of 7′-aminonaltrindole as a selective δ-opioid receptor affinity label
Haris, Sarika Prabhu,Zhang, Yan,Le Bourdonnec, Bertrand,McCurdy, Christopher R.,Portoghese, Philip S.
, p. 3392 - 3396 (2008/02/09)
Incorporation of a naphthalene-dialdehyde moiety into the δ antagonist, 6′-aminonaltrindole afforded a potent, selective, irreversible δ-agonist 1. However, flow cytometry studies revealed no time-dependent specific fluorescence, suggesting that both Lys2
Affinity labels as tools for the identification of opioid receptor recognition sites
Portoghese, Philip S.,El Kouhen, Rachid,Law, Ping Y.,Loh, Horace H.,Le Bourdonnec, Bertrand
, p. 191 - 196 (2007/10/03)
Affinity labels have proven to be useful tools in opioid research. We review experiments carried out with the μ opioid receptor affinity label, β-funaltrexamine (2), that support the concept of different recognition sites for μ opioid agonists and antagon
Synthesis of Phthalocyanines with One Sulfonic Acid, Carboxylic acid, or Amino Group
Kliesh, Holger,Weitemeyer, Andrea,Mueller, Silke,Woehrle, Dieter
, p. 1269 - 1274 (2007/10/02)
Monofuntional phthalocyanines 7a,b, one bearing a sulfo and the other one a carboxyl group, were synthesized by lithium alkoxyde-catalyzed statistical tetramerization of 4-(4-tert-butylphenoxy)-1,2-benzenedicarbonitrile (3c) with 1,2-dicyanobenzenes 3a,b
