The New Salicylaldehyde S,S-Propanedithioacetal Ester Enables N-to-C Sequential Native Chemical Ligation and Ser/Thr Ligation for Chemical Protein Synthesis
- 13 May 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 142 (19), 8790-8799
- https://doi.org/10.1021/jacs.0c01561
Abstract
The combination of distinct peptide ligation techniques to facilitate chemical protein synthesis represents one of the long-standing goals in the field. A new combination ligation method of N-to-C sequential native chemical ligation and Ser/Thr ligation (NCL-STL) is described for the first time. This method relies on the peptide salicylaldehyde S,S-propanedithioacetal (SAL(PDT))-ester prepared by a new 1,3-propanedithiol-mediated reaction. The peptide SAL(PDT)-ester, which is compatible with NCL, can be fully activated by N-chlorosuccinimide (NCS)/AgNO3 in aqueous solution to afford peptide SAL-ester for use in the subsequent STL. The practicality of the combined NCL-STL method is illustrated by the synthesis of S-palmitoylated matrix-2 (S-palm M2) ion channel from Influenza A virus and S-palmitoylated interferon-induced transmembrane protein 3 (S-palm IFITM3). This approach expands the multiple-segments peptide ligation toolkit for producing important and complex custom-made protein samples by chemical protein synthesis.Funding Information
- Ministry of Science and Technology of the People's Republic of China (2017YFA0505200, 2019YFA0706902)
- National Natural Science Foundation of China (21532004, 81621002, 91753120, U1732161)
- Anhui Province (1808085J04)
- Innovative Program Development Foundation of Hefei Center Physical Science and Technology (2017FXCX002)
This publication has 64 references indexed in Scilit:
- Convergent Chemical Synthesis of Proteins by Ligation of Peptide HydrazidesAngewandte Chemie, 2012
- Sequential native peptide ligation strategies for total chemical protein synthesisChemical Society Reviews, 2012
- IFITM3 restricts the morbidity and mortality associated with influenzaNature, 2012
- Chemical Protein Synthesis by Chemoselective α‐Ketoacid–Hydroxylamine (KAHA) Ligations with 5‐OxaprolineAngewandte Chemie, 2012
- A One‐Pot Three‐Segment Ligation Strategy for Protein Chemical SynthesisAngewandte Chemie, 2011
- Palmitoylome profiling reveals S-palmitoylation–dependent antiviral activity of IFITM3Nature Chemical Biology, 2010
- Free‐Radical‐Based, Specific Desulfurization of Cysteine: A Powerful Advance in the Synthesis of Polypeptides and GlycopolypeptidesAngewandte Chemie-International Edition, 2007
- Supramolecular Allosteric Cofacial Porphyrin ComplexesJournal of the American Chemical Society, 2006
- A Highly Efficient Procedure for Regeneration of Carbonyl Groups from their Corresponding Oxathioacetals and Dithioacetals Using Sodium Nitrite and Acetyl Chloride in DichloromethaneSynlett, 2003
- The S,S-acetal to carbonyl transformation using the soft NO+or Cl+speciesJournal of the Chemical Society, Perkin Transactions 1, 1983