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Volumn 48, Issue 41, 2009, Pages 7591-7594

Triblock peptide and peptide thioester synthesis with reactivity- differentiated sulfonamides and peptidyl thioacids

Author keywords

Chemical ligation; Nucleophilic aromatic substitution; Peptide synthesis; Thioacids; Thioesters

Indexed keywords

CHEMICAL LIGATION; NUCLEOPHILIC AROMATIC SUBSTITUTION; PEPTIDE SYNTHESIS; THIOACIDS; THIOESTERS;

EID: 70349991008     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200903050     Document Type: Article
Times cited : (47)

References (33)
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    • note
    • Within the limits of our NMR and UPLC detection methods the couplings reported in this manuscript proceed without racemization. In preliminary studies on the thioacid-sulfonamide method, and on the related thioacid-amine-Sangers/ Mukaiyama approach, this was rigorously established through the synthesis of authentic samples of epimeric products.[6a, 7]
  • 33
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    • note
    • With cesium carbonate the N-FNS protected di- and higher peptide thioacids were observed by mass spectrometry to undergo cyclization, with retention of the FNS group, rather than condensation when exposed to a DNS peptide and cesium carbonate. This was attributed to the acidity of the FNS sulfonamide NH group and so was circumvented by the use of the milder base. The use of pyridine as base afforded a similar result to cesium carbonate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.