Thioester
Thioester — A compound containing a sulfur-carbon double bond linkage, used as a reactive intermediate in native chemical ligation of peptide fragments.
What Is a Thioester?
A thioester is a chemical bond between a carbonyl group (C=O) and a sulfur atom (C(=O)-S-R). In peptide chemistry, thioesters are critical intermediates in native chemical ligation (NCL) and are also found in nature as the high-energy intermediates of non-ribosomal peptide synthesis and ubiquitin transfer.
Applications
- NCL: C-terminal peptide thioesters react with N-terminal cysteine to form native peptide bonds
- Expressed protein ligation (EPL): Intein-generated recombinant protein thioesters for semi-synthesis
- CoA thioesters: Acetyl-CoA, malonyl-CoA are thioester-linked metabolic intermediates
- Ubiquitin activation: E1 enzyme forms a thioester with ubiquitin's C-terminal glycine
Frequently Asked Questions
What is Thioester?
A compound containing a sulfur-carbon double bond linkage, used as a reactive intermediate in native chemical ligation of peptide fragments.
Why is Thioester important in peptide research?
Thioester is a fundamental concept in chemistry as it relates to peptide science. It directly influences experimental design, compound characterization, and the reliability of research outcomes across biochemistry and molecular biology disciplines.