Application of the O-N intramolecular acyl migration reaction in medicinal chemistry

Skwarczynski, Mariusz and Kiso, Yoshiaki (2007) Application of the O-N intramolecular acyl migration reaction in medicinal chemistry. Current Medicinal Chemistry, 14 26: 2813-2823. doi:10.2174/092986707782360123


Author Skwarczynski, Mariusz
Kiso, Yoshiaki
Title Application of the O-N intramolecular acyl migration reaction in medicinal chemistry
Journal name Current Medicinal Chemistry   Check publisher's open access policy
ISSN 0929-8673
1875-533X
Publication date 2007-11
Sub-type Article (original research)
DOI 10.2174/092986707782360123
Volume 14
Issue 26
Start page 2813
End page 2823
Total pages 11
Place of publication Bussum, Netherlands
Publisher Bentham Science Publishers
Language eng
Formatted abstract The O-N intramolecular acyl migration, also named as an acyl shift or acyl transfer reaction, is well-known in organic and peptide chemistry as a simple rearrangement which proceeds under very mild aqueous conditions. Despite a long history with this reaction, its application in medicinal chemistry has only lately been proposed. In the last decade, this reaction has been intensively studied and several applications of this rearrangement in medicinal chemistry have appeared. O-N Intramolecular acyl migration has been employed in "no auxiliary, no byproduct" prodrug strategies (prodrugs of paclitaxel and other taxoids, prodrugs of HIV protease inhibitors), for the synthesis of peptides containing difficult sequences via "O-acyl isopeptide method", including Alzheimer's disease related amyloid β peptide (Aβ) 1-42, and in the design of pH-, photo- or enzyme-triggered click peptides, as a potential powerful tool for identifying the pathological functions of amyloid β peptides in Alzheimer's disease. This review summarized recent advances in the application of O-N intramolecular acyl migration with special focus on medicinal chemistry.
© 2007 Bentham Science Publishers Ltd.
Keyword O–N Intramolecular acyl migration
O–N intramolecular acyl shift
O–N intramolecular acyl transfer
HIV protease inhibitor prodrugs
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: School of Chemistry and Molecular Biosciences
 
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Created: Sun, 20 Mar 2011, 23:17:52 EST by Dr Mariusz Skwarczynski on behalf of School of Chemistry & Molecular Biosciences