928342-24-9Relevant academic research and scientific papers
Direct acyl substitution of carboxylic acids: A chemoselective o- to N-acyl migration in the traceless staudinger ligation
Kosal, Andrew D.,Wilson, Erin E.,Ashfeld, Brandon L.
supporting information, p. 14444 - 14453,10 (2020/09/16)
A chlorophosphite-modified, Staudinger-like acylation of azides involving a highly chemoselective, direct nucleophilic acyl substitution of carboxylic acids is described. The reaction provides the corresponding amides with analytical purity in 32-97 % yield after a simple aqueous workup without the need for a pre-activation step. The use of chlorophosphites as dual carboxylic acid-azide activating agents enables the formation of acyl C-N bonds in the presence of a wide range of nucleophilic and electrophilic functional groups, including amines, alcohols, amides, aldehydes, and ketones. The coupling of carboxylic acids and azides for the formation of alkyl amides, sulfonyl amides, lactams, and dipeptides is described. Copyright
Facile peptide thioester synthesis via solution-phase tosylamide preparation
Manabe, Shino,Sugioka, Tomoyuki,Ito, Yukishige
, p. 849 - 853 (2007/10/03)
Preparation of peptide thioester is essential for native chemical ligation and block condensation. Our novel methodology involves conversion of the carboxylic acid of a peptide into a thioester using p-toluenesulfonyl isocyanate, followed by alkylation, t
