Acid-mediated prevention of aspartimide formation in solid phase peptide synthesis

Aspartimide formation is one of the major obstacles that impedes the solid phase synthesis of large peptides and proteins. Until now, no cost-effective strategy to suppress this side reaction has been developed. Here it is demonstrated that addition of small amounts of organic acids to the standard...

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Hauptverfasser: Michels, Tillmann (VerfasserIn) , Dölling, Rudolf (VerfasserIn) , Haberkorn, Uwe (VerfasserIn) , Mier, Walter (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: October 1, 2012
In: Organic letters
Year: 2012, Jahrgang: 14, Heft: 20, Pages: 5218-5221
ISSN:1523-7052
DOI:10.1021/ol3007925
Online-Zugang:Verlag, Volltext: http://dx.doi.org/10.1021/ol3007925
Verlag, Volltext: https://doi.org/10.1021/ol3007925
Volltext
Verfasserangaben:Tillmann Michels, Rudolf Dölling, Uwe Haberkorn, Walter Mier
Beschreibung
Zusammenfassung:Aspartimide formation is one of the major obstacles that impedes the solid phase synthesis of large peptides and proteins. Until now, no cost-effective strategy to suppress this side reaction has been developed. Here it is demonstrated that addition of small amounts of organic acids to the standard Fmoc cleavage agent piperidine efficiently prevents formation of aspartimide side products. This effect is shown to be virtually independent of the acid strength.
Beschreibung:Gesehen am 29.11.2018
Beschreibung:Online Resource
ISSN:1523-7052
DOI:10.1021/ol3007925