1402348-91-7Relevant academic research and scientific papers
Metal-Free, Site-Selective Peptide Modification by Conversion of “Customizable” Units into β-Substituted Dehydroamino Acids
Saavedra, Carlos J.,Hernández, Dácil,Boto, Alicia
, p. 599 - 607 (2018)
Our site-selective modification of serine or threonine units in peptides allows the generation of β-substituted dehydroamino acids, which increase peptide resistance to hydrolysis and may improve their biological properties. Both the terminal and internal positions can be modified, and different customizable units can be activated separately. Remarkably, high Z selectivity is achieved, even at internal positions. The conversion involves a one-pot oxidative radical scission/phosphorylation process by using the low-toxicity (diacetoxyiodo)benzene/iodine system as the scission reagent. The resulting α-amino phosphonates undergo a Horner-Wadsworth-Emmons reaction to produce the dehydroamino acid derivatives (in a Z/E ratio of usually >98:2) under mild and metal-free conditions.
Customizable units in Di- and tripeptides: Selective conversion into substituted dehydroamino acids
Saavedra, Carlos J.,Boto, Alicia,Hernandez, Rosendo
supporting information; experimental part, p. 3788 - 3791 (2012/09/08)
The selective conversion of serine or threonine units of di- and tripeptides into substituted dehydroamino acids is reported. Thus, these common α-amino acids undergo a scission-phosphorylation process to give α-amino phosphonate residues. A Horner-Wadsworth-Emmons reaction with aldehydes or ketones follows to afford the final products with excellent Z-stereoselectivity (Z:E > 98:2). In this way, a single peptide precursor can selectively be transformed into a variety of derivatives.
