81000-39-7Relevant articles and documents
α-Methylphenacyl thioesters as convenient thioacid precursors
Hatanaka, Toru,Yuki, Ryosuke,Saito, Ryota,Sasaki, Kaname
supporting information, p. 10589 - 10592 (2016/11/30)
α-Methylphenacyl (Mpa) thioesters are described as precursors of thioacids. Mpa thioesters are accessible via the condensation of carboxylic acids and phenacyl thiol, which is easily prepared without column chromatography. The Mpa thioesters are selectively deprotected by reduction with zinc dust in the presence of conventional thioacid protecting groups. In addition, the Mpa group exhibits orthogonal reactivity to the Boc group. These features are expected to facilitate the preparation of complex thioacids, including those in peptides.
Thioacetic acid/NaSH-mediated synthesis of N -protected amino thioacids and their utility in peptide synthesis
Mali, Sachitanand M.,Gopi, Hosahudya N.
, p. 2377 - 2383 (2014/04/17)
Thioacids are recently gaining momentum due to their versatile reactivity. The reactivity of thioacids has been widely explored in the selective amide/peptide bond formation. Thioacids are generally synthesized from the reaction between activated carboxylic acids such as acid chlorides, active esters, etc., and Na2S, H2S, or NaSH. We sought to investigate whether the versatile reactivity of the thioacids can be tuned for the conversion of carboxylic acids into corresponding thioacids in the presence of NaSH. Herein, we report that thioacetic acid- and NaSH-mediated synthesis of N-protected amino thioacids from the corresponding N-protected amino acids, oxidative dimerization of thioacids, crystal conformations of thioacid oxidative dimers, and the utility of thioacids and oxidative dimers in peptide synthesis. Our results suggest that peptides can be synthesized without using standard coupling agents.
T3P (propylphosphonic anhydride) mediated conversion of N α-protected amino/peptide acids into thioacids
Madhu, Chilakapati,Basavaprabhu,Vishwanatha,Sureshbabu, Vommina V.
experimental part, p. 1406 - 1409 (2012/03/27)
A general, mild and an efficient protocol, which makes use of T3P as an acid activator for the synthesis of Nα-protected amino/peptide thioacids from corresponding acids in the presence of finely ground Na 2S as hydrosulfide ion donor is described. The protocol employed significantly increases the overall efficiency as the yield, reaction duration and purity of even sterically hindered amino acids.