Late-stage installation of dehydroamino acid motifs into peptides enabled by an N-chloropeptide strategy was written by Nanjo, Takeshi;Oshita, Takuma;Matsumoto, Ayaka;Takemoto, Yoshiji. And the article was included in Chemistry – A European Journal in 2022.Category: chlorides-buliding-blocks This article mentions the following:
Conventional methods for the construction of dehydroamino acids (ΔAAs), which are a unique class of non-proteinogenic amino acids, require the pre-installation of special amino acids. Herein, we report and demonstrate the practical utility of an N-chloropeptide strategy for the rapid construction of ΔAA-containing peptides. The electrophilic N-chlorination of peptide bonds is drastically accelerated by a catalytic amount of quinuclidine (ABCO), and the subsequent β-elimination of N-chloroamide efficiently provides ΔAA-containing peptides in high yield. The strategy enables, for the first time, the construction of a wide variety of ΔAA residues in peptides without any pre-functionalized side chains and facilitates the late-stage installation of ΔAA motifs into already-constructed oligopeptides, including a medicinally important macrocyclic peptide. In the experiment, the researchers used many compounds, for example, 2-Chlorobenzo[d]isothiazol-3(2H)-one 1,1-dioxide (cas: 14070-51-0Category: chlorides-buliding-blocks).
2-Chlorobenzo[d]isothiazol-3(2H)-one 1,1-dioxide (cas: 14070-51-0) belongs to organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. Aliphatic organochlorides are often alkylating agents as chlorine can act as a leaving group, which can result in cellular damage.Category: chlorides-buliding-blocks
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics