1044285-13-3Relevant academic research and scientific papers
Synthesis of cysteine-rich peptides by native chemical ligation without use of exogenous thiols
Tsuda, Shugo,Yoshiya, Taku,Mochizuki, Masayoshi,Nishiuchi, Yuji
, p. 1806 - 1809 (2015)
Native chemical ligation (NCL) performed without resorting to the use of thiol additives was demonstrated to be an efficient and effective procedure for synthesizing Cys-rich peptides. This method using tris(2-carboxyethyl)phosphine (TCEP) as a reducing agent facilitates the ligation reaction even at the Thr-Cys or Ile-Cys site and enables one-pot synthesis of Cys-rich peptides throughout NCL and oxidative folding.
Sulfanylmethyldimethylaminopyridine as a Useful Thiol Additive for Ligation Chemistry in Peptide/Protein Synthesis
Ohkawachi, Kento,Kobayashi, Daishiro,Morimoto, Kyohei,Shigenaga, Akira,Denda, Masaya,Yamatsugu, Kenzo,Kanai, Motomu,Otaka, Akira
, p. 5289 - 5293 (2020)
Sulfanylmethyl-installed dimethylaminopyridine, 2-sulfanylmethyl-4-dimethylaminopyridine (2), has an acidic thiol group comparable to that in aryl thiols due to the formation of a zwitterion consisting of a thiolate anion and a pyridinium cation. It can be used as an additive for native chemical ligation. The alkyl thiol in 2 allows it to be used for the one-pot native chemical ligation-desulfurization protocol in peptide synthesis. The utility of 2 in the synthesis of cyclic peptides is demonstrated.
Trifluoroethanethiol: An additive for efficient one-pot peptide ligation - Desulfurization chemistry
Thompson, Robert E.,Liu, Xuyu,Alonso-García, Noelia,Pereira, Pedro José Barbosa,Jolliffe, Katrina A.,Payne, Richard J.
supporting information, p. 8161 - 8164 (2014/06/24)
Native chemical ligation followed by desulfurization is a powerful strategy for the assembly of proteins. Here we describe the development of a high-yielding, one-pot ligation-desulfurization protocol that uses trifluoroethanethiol (TFET) as a novel thiol additive. The synthetic utility of this TFET-enabled methodology is demonstrated by the efficient multi-step one-pot syntheses of two tick-derived proteins, chimadanin and madanin-1, without the need for any intermediary purification.
