Spontaneous head-to-tail cyclization of unprotected linear peptides with the KAHA ligation
Bode, Jeffrey W.
- Journal Article
Rights / licenseCreative Commons Attribution-NonCommercial 3.0 Unported
The α-ketoacid–hydroxylamine (KAHA) ligation with 5-oxaproline enables the direct cyclization of peptides upon cleavage from a solid support, without coupling reagents, protecting groups, or purification of the linear precursors. This Fmoc SPPS-based method was applied to the synthesis of a library of 24 homoserine-containing cyclic peptides and was compared side-by-side with the synthesis of the same products using a standard method for cyclizing side-chain protected substrates. A detailed mechanistic study including 2H and 18O labeling experiments and the characterization of reaction intermediates by NMR and mass spectrometry is reported. Show more
Journal / seriesChemical Science
Pages / Article No.
PublisherRoyal Society of Chemistry
Organisational unit03861 - Bode, Jeffrey W. / Bode, Jeffrey W.
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