SEA native peptide ligation

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The SEA native peptide ligation is a biochemical method for protein ligation by linking two or more peptides .

properties

Reaction scheme of the SEA native peptide ligation

The N -terminal peptide must for protein ligation as the last amino acid (at its C -terminus ) a bis (2-sulfanylethyl) amino group (SEA) and the C -terminal peptide has for protein ligation as first amino acid (at its N -terminus ) have a cysteine or homocysteine . In the course of the ligation, a thioester bond is formed on the SEA peptide , which is transesterified and then rearranged to form a peptide bond (thiotransesterification and S, N-acyl shift ). As catalyst is mercaptophenylacetic acid (MPAA) is used.

Alternative methods of protein ligation have been described, e.g. B. native chemical ligation , prior thiol capture , expressed protein ligation , acyl-initiated capture and peptide ligation with selenocysteine .

history

This was developed independently from 2010 by the working group around O. Melnyk and the working group around CF Liu.

Individual evidence

  1. ↑ TW Muir, D. Sondhi, PA Cole: Expressed protein ligation: a general method for protein engineering. In: Proceedings of the National Academy of Sciences . Volume 95, Number 12, June 1998, ISSN  0027-8424 , pp. 6705-6710, PMID 9618476 , PMC 22605 (free full text).
  2. ↑ BL Nilsson, MB Soellner, RT Raines: Chemical synthesis of proteins. In: Annual review of biophysics and biomolecular structure. Volume 34, 2005, ISSN  1056-8700 , pp. 91-118, doi : 10.1146 / annurev.biophys.34.040204.144700 , PMID 15869385 , PMC 2845543 (free full text).
  3. ↑ N. Ollivier, J. Dheur, R. Mhidia, A. Blanpain, O. Melnyk: Bis (2-sulfanylethyl) amino native peptide ligation. In: Organic letters. Volume 12, Number 22, November 2010, ISSN  1523-7052 , pp. 5238-5241, doi : 10.1021 / ol102273u , PMID 20964289 .
  4. ^ W. Hou, X. Zhang, F. Li, CF Liu: Peptidyl N, N-bis (2-mercaptoethyl) -amides as thioester precursors for native chemical ligation. In: Organic letters. Volume 13, Number 3, February 2011, ISSN  1523-7052 , pp. 386-389, doi : 10.1021 / ol102735k , PMID 21175148 .