Solid phase synthesis of peptide-selenoesters

Ghassemian, Artin, Vila-Farres, Xavier, Alewood, Paul F. and Durek, Thomas (2013) Solid phase synthesis of peptide-selenoesters. Bioorganic and Medicinal Chemistry, 21 12: 3473-3478. doi:10.1016/j.bmc.2013.03.076

Author Ghassemian, Artin
Vila-Farres, Xavier
Alewood, Paul F.
Durek, Thomas
Title Solid phase synthesis of peptide-selenoesters
Journal name Bioorganic and Medicinal Chemistry   Check publisher's open access policy
ISSN 1464-3391
Publication date 2013-06
Sub-type Article (original research)
DOI 10.1016/j.bmc.2013.03.076
Volume 21
Issue 12
Start page 3473
End page 3478
Total pages 6
Place of publication Kidlington, Oxford, United Kingdom
Publisher Pergamon
Collection year 2014
Language eng
Abstract The synthesis of proteins by native chemical ligation greatly enhances the application of chemistry to complex molecules such as proteins. The essential building blocks for this approach traditionally have been peptide-thioester segments that are linked chemoselectively in consecutive reactions. By using peptide selenoesters instead of thioesters, the ligation rate can be significantly accelerated permitting couplings at difficult sites and potentially enabling new ligation strategies. To facilitate the routine synthesis of selenoester peptides, a general and straightforward procedure has been developed that generates a suitably functionalized resin from which the desired selenoester peptide can be readily synthesized. This simple approach utilizes readily available and cheap chemical agents and enables production of peptide selenoesters of excellent quality in short time and with high recovery. In addition, the stability of peptide selenoesters was examined under different native chemical ligation conditions and compared to thioesters. Selenoesters are slightly more reactive and more susceptible to hydrolysis and aminolysis than thioesters but sufficiently stable under mildly acidic conditions (pH 6.5). Under these conditions, rapid selenoester-mediated ligation is kinetically favoured.
Keyword Native chemical ligation
Solid phase peptide synthesis
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2014 Collection
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