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DOI: 10.1055/s-0037-1611463
Chemical Ligation of Unprotected Peptide Segments
Publikationsverlauf
Publikationsdatum:
15. Februar 2019 (online)
![](https://www.thieme-connect.de/media/synfacts/201903/i_h001_s1_10-1055_s-0037-1611463.gif)
Significance
The authors describe an approach for the chemical ligation of peptide segments by thiazolidine ring formation. The method does not require protecting groups or the activation of the Cα-carboxyl group in the conventional sense. The main feature of the approach is that it overcomes the entropy barrier to intermolecular reaction between two large molecules. Furthermore, this method was successfully used in the synthesis of a pentadecapeptide.
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Comment
This chemical ligation approach of unprotected segments proceeds through three steps: (1) introduction of an aldehyde group at a C-terminal site, (2) ring formation, and (3) O-to-N acyl transfer. These steps eliminate the need for protecting groups and permit the ligation to proceed in aqueous solution.
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![](https://www.thieme-connect.de/media/synfacts/201903/i_h001_s1_10-1055_s-0037-1611463.gif)