Thiazolidine-Masked α-Oxo Aldehyde Functionality for Peptide and Protein Modification was written by Bi, Xiaobao;Pasunooti, Kalyan Kumar;Lescar, Julien;Liu, Chuan-Fa. And the article was included in Bioconjugate Chemistry in 2017.Name: Thiazolidine-2-carboxylic acid This article mentions the following:
α-Oxo aldehyde-based bioconjugation chem. has been widely explored in peptide and protein modifications for various applications in biomedical research during the past decades. The generation of α-oxo aldehyde via sodium periodate oxidation is usually limited to the N-terminus of a target protein. Internal-site functionalization of proteins with the α-oxo aldehyde handle has not been achieved yet. Herein the authors report a novel method for site-specific peptide and protein modification using synthetically or genetically incorporated thiazolidine-protected α-oxo aldehyde. Efficient unmasking of the aldehyde was achieved by silver ion-mediated hydrolysis of thiazolidine under mild conditions for the first time. A model peptide and a recombinant protein were used to demonstrate the utility of this new method, which were site-specifically modified by oxime ligation with an oxyamine-functionalized peptide labeling reagent. Therefore, the authors’ current method has enriched the α-oxo aldehyde synthetic tool box in peptide and protein bioconjugation chem. and holds great potential to be explored in novel applications in the future. In the experiment, the researchers used many compounds, for example, Thiazolidine-2-carboxylic acid (cas: 16310-13-7Name: Thiazolidine-2-carboxylic acid).
Thiazolidine-2-carboxylic acid (cas: 16310-13-7) belongs to thiazolidine derivatives. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. Thiazolidines have been applied as prodrug derivatives for various steroids containing a 3-carbonyl group to improve their topical anti-inflammatory activity. Name: Thiazolidine-2-carboxylic acid
Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com