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Issue 12, 2014
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A highly efficient in situ N-acetylation approach for solid phase synthesis

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Abstract

We describe a new general N-acetylation method for solid phase synthesis. Malonic acid is used as a precursor and the reaction proceeds by in situ formation of a reactive ketene intermediate at room temperature. We have successfully applied this methodology to peptides and non-peptidic molecules containing a variety of functional groups. The reaction gave high yields compared to known acetylation methods, irrespective of the structure, conformation and sequence of the acetylated molecule. Computational studies revealed that the concerted mechanism via the ketene intermediate is kinetically favorable and leads to a thermodynamically stable acetylated product. In conclusion, our method can be easily applied to acetylation in a wide variety of chemical reactions performed on the solid phase.

Graphical abstract: A highly efficient in situ N-acetylation approach for solid phase synthesis

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Publication details

The article was received on 21 Oct 2013, accepted on 21 Jan 2014 and first published on 21 Jan 2014


Article type: Paper
DOI: 10.1039/C3OB42096E
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 1879-1884
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    A highly efficient in situ N-acetylation approach for solid phase synthesis

    K. Chandra, T. K. Roy, J. N. Naoum, C. Gilon, R. B. Gerber and A. Friedler, Org. Biomol. Chem., 2014, 12, 1879
    DOI: 10.1039/C3OB42096E

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