2018年4月20日
Resin-Bound Crypto-Thioester for Native Chemical Ligation
Organic Letters
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- ,
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- 巻
- 20
- 号
- 8
- 開始ページ
- 2449
- 終了ページ
- 2453
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/acs.orglett.8b00795
- 出版者・発行元
- American Chemical Society
The resin-bound N-sulfanylethylanilide (SEAlide) peptide was found to function as a crypto-thioester peptide. Exposure of the peptide resin to an aqueous solution under neutral conditions in the presence of thiols affords thioesters without accompanying racemization of C-terminal amino acids. Furthermore, the resin-bound SEAlide peptides react with N-terminal cysteinyl peptides in the absence of phosphate salts to afford ligated products, whereas soluble SEAlide peptides do not. This unexpected difference in reactivity of the SEAlide peptides allows for a one-pot/three-fragment ligation using resin-bound and unbound peptides.
- リンク情報
- ID情報
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- DOI : 10.1021/acs.orglett.8b00795
- ISSN : 1523-7052
- ISSN : 1523-7060
- PubMed ID : 29629775
- SCOPUS ID : 85045755044
- Web of Science ID : WOS:000430898200075