Development of Synthetic Methods for Peptide Thioesters Based on the N-S Acyl Shift Reaction

DOI 1 Citations 58 References

Bibliographic Information

Other Title
  • Ｎ‐Ｓアシル基転位反応を用いるペプチドチオエステル合成法の開発

Abstract

Peptide thioesters are used as key building blocks for contemporary protein synthesis, based on the ligation strategy such as thioester method and native chemical ligation. We found the methods for preparation of the peptide thioesters, in which the key reaction is an intramolecular N-S acyl shift reaction of thiol-containing peptides. These processes can be applied to Fmoc based solid phase peptide synthesis with minimum racemization at the thioester position. For the N-S acyl shift reaction, we use an N-2-mercapto-4,5-dimethoxybenzyl (Dmmb) group on the peptide bond, or a cysteine residue. The Dmmb-containing peptide is readily converted to the corresponding 2-sulfoethyl thioester via the N-S acyl shift reaction, followed by the intermolecular thiol-thioester exchange reaction. A peptide containing a Cys-Pro ester (CPE) moiety is spontaneously transformed into a diketopiperazine (DKP) thioester under neutral conditions. Furthermore, a peptide containing a Cys-Pro-Cys (CPC) sequence was also transformed into a peptide DKP thioester under acidic conditions via the N-S acyl shift reaction.

Journal

Citations (1)*help

See more

References(58)*help

See more

Keywords

Details 詳細情報について

  • CRID
    1390001205340125568
  • NII Article ID
    130002143002
  • DOI
    10.5059/yukigoseikyokaishi.70.166
  • ISSN
    18836526
    00379980
  • Text Lang
    ja
  • Data Source
    • JaLC
    • Crossref
    • CiNii Articles
  • Abstract License Flag
    Disallowed

Report a problem

Back to top