Native chemical ligation at valine: A contribution to peptide and glycopeptide synthesis Journal Article

   


Authors: Chen, J.; Wan, Q.; Yuan, Y.; Zhu, J.; Danishefsky, S. J.
Article Title: Native chemical ligation at valine: A contribution to peptide and glycopeptide synthesis
Abstract: (Chemical Equation Presented) A Val-uable link: The title transformation is achieved by a two-step ligation, radicalbased desulfurization strategy (see scheme; NCL=native chemical ligation). After S→N acyl transfer, in which the acyl acceptor is a γ-thiol valine derivative, and site-specific dethiolation, a valine residue appears at the site of ligation. This method accomplishes ligations at Thr-Val and Pro-Val sites, and allows successful ligation of glycopeptide fragments. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
Keywords: chemistry; amines; peptides; chemical reactions; chemical equations; synthesis; synthesis (chemical); glycopeptide; glycopeptides; desulfurization; native chemical ligation; surgical equipment; valine; mathematical transformations; acyl acceptors; acyl transfers; glycopeptide syntheses; native chemical ligations
Journal Title: Angewandte Chemie - International Edition
Volume: 47
Issue: 44
ISSN: 1433-7851
Publisher: Wiley Blackwell  
Date Published: 2008-10-20
Start Page: 8521
End Page: 8524
Language: English
DOI: 10.1002/anie.200803523
PUBMED: 18833563
PROVIDER: scopus
PMCID: PMC2756581
DOI/URL:

http://www.scopus.com/inward/record.url?eid=2-s2.0-54249149331&partnerID=40&md5=87c4bcc67804f07d03f90b238cf7f957
Notes: --- - "Cited By (since 1996): 42" - "Export Date: 17 November 2011" - "CODEN: ACIEA" - "Source: Scopus"
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MSK Authors
  1. Qian Wan
    23 Wan
  2. Yu Yuan
    11 Yuan
  3. Jin Chen
    5 Chen
  4. Jianglong Zhu
    14 Zhu
  5. Samuel J Danishefsky
    539 Danishefsky
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