Liu, Minglong; Sovrovic, Miha; Suga, Hiroaki; Jongkees, Seino A. K. published an article in 2022, the title of the article was Phosphine addition to dehydroalanine for peptide modification.SDS of cas: 79642-50-5 And the article contains the following content:
Thiols are a functional group commonly used for selective reactions in a biochem. setting because of their high nucleophilicity. Phosphorus nucleophiles can undergo some similar reactions to thiols, but remain underexploited in this setting. In this work we show that phosphine nucleophiles react cleanly and quickly with a dehydroalanine electrophile, itself generated from cysteine, to give a stable adduct in a peptide context. NMR reveals the product to be a phosphonium ion and indicates some backbone conformational constraint, possibly arising from transient carbonyl coordination. The reaction proceeded quickly, with a pseudo-first order rate constant of 0.126 min-1 at 1 mM peptide (80% conversion in 10 min), and with no detectable side products on the peptide. A broad peptide sequence scope and water-soluble phosphines with alkyl as well as aromatic groups were all shown to react efficiently. Phosphine addition proved to be efficient on nisin as a model Dha-containing biol.-derived peptide and on an mRNA-displayed peptide, as well as on TCEP-modified agarose for peptide capture from solution This reaction thus presents a promising approach for modification of peptides for cargo attachment or altered phys. properties in peptide discovery. The experimental process involved the reaction of Bis(2,5-dioxopyrrolidin-1-yl) glutarate(cas: 79642-50-5).SDS of cas: 79642-50-5
The Article related to phosphine addition dehydroalanine peptide modification thiol cysteine, peptide addition phosphine reaction kinetics product distribution decomposition stability, solid phase peptide synthesis phosphine addition, nisin rna peptide phosphine addition and other aspects.SDS of cas: 79642-50-5
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