5724-76-5Relevant articles and documents
Maleimide conjugates of saxitoxin as covalent inhibitors of voltage-gated sodium channels
Parsons, William H.,Du Bois
, p. 10582 - 10585 (2013)
(+)-Saxitoxin, a naturally occurring guanidinium poison, functions as a potent, selective, and reversible inhibitor of voltage-gated sodium ion channels (NaVs). Modified forms of this toxin bearing cysteine-reactive maleimide groups are available through total synthesis and are found to irreversibly inhibit sodium ion conductance in recombinantly expressed wild-type sodium channels and in hippocampal nerve cells. Our findings support a mechanism for covalent protein modification in which toxin binding to the channel pore precedes maleimide alkylation of a nucleophilic amino acid. Second-generation maleimide-toxin conjugates, which include bioorthogonal reactive groups, are also found to block channel function irreversibly; such compounds have potential as reagents for selective labeling of NaVs for live cell imaging and/or proteomics experiments.
Regioselective β-Csp3-Arylation of β-Alanine: An Approach for the Exclusive Synthesis of Diverse β-Aryl-β-amino Acids
Chowdhury, Sushobhan,Vaishnav, Roopal,Panwar, Namita,Haq, Wahajul
, p. 2512 - 2522 (2019/03/07)
An approach for the synthesis of a variety of new β-aryl-β-amino acids has been developed via a palladium-catalyzed auxiliary-directed regioselective Csp3-H arylation of the unactivated β-methylene bond of β-alanine. The use of 8-aminoquinoline amide as an auxiliary efficiently directs the desired regioselective β-Csp3-H functionalization. The developed protocol enables the easy and straightforward access to several high-value β-aryl-β-amino acids useful for peptide engineering, starting from inexpensive and readily available β-alanine precursors in moderate to excellent yields.
Sulfonium ylides 7. Influence of substituents in the imide fragment on the regioselectivity of intramolecular cyclization of phthalimido-containing keto-stabilized sulfonium ylides
Galin,Lakeev,Tolstikov
, p. 1904 - 1908 (2007/10/03)
The intramolecular cyclization of keto-stabilized sulfonium ylides obtained from β-alanine and containing various imide fragments was studied. On heating in toluene in the presence of PhCO2H, ylides containing a phthalimide moiety are converted into indolizidine-2,6-dione derivatives, whereas those incorporating a 4-methyl-1,2,3,6-tetrahydrophthalimide or pyrrolidine-2,5-dione moieties do not undergo cyclization.