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

書誌事項

タイトル別名
  • Development of Synthetic Methods for Peptide Thioesters Based on the N-S Acyl Shift Reaction

抄録

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.

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被引用文献 (1)*注記

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詳細情報 詳細情報について

  • CRID
    1390001205340125568
  • NII論文ID
    130002143002
  • DOI
    10.5059/yukigoseikyokaishi.70.166
  • ISSN
    18836526
    00379980
  • 本文言語コード
    ja
  • データソース種別
    • JaLC
    • Crossref
    • CiNii Articles
  • 抄録ライセンスフラグ
    使用不可

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