Synthesis and Evaluation of Cyclic Acetals of Serine Hydroxylamine for Amide-Forming KAHA Ligations
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Date
2019-03-01Type
- Journal Article
ETH Bibliography
yes
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Abstract
The α-ketoacid–hydroxylamine (KAHA) ligation allows the coupling of unprotected peptide segments. The most widely used variant employs a 5-membered cyclic hydroxylamine that forms a homoserine ester as the primary ligation product. While very effective, monomers that give canonical amino acid residues are in high demand. In order to preserve the stability and reactivity of cyclic hydroxylamines, but form a canonical amino acid residue upon ligation, we sought to prepare cyclic derivatives of serine hydroxylamine. An evaluation of several cyclization strategies led to cyclobutanone ketals as the leading structures. The preparation, stability, and amide-forming ligation of these serine-derived ketals are described. Show more
Permanent link
https://doi.org/10.3929/ethz-b-000331214Publication status
publishedExternal links
Journal / series
SynthesisVolume
Pages / Article No.
Publisher
ThiemeSubject
Ligation; Hydroxylamines; Acetals; Amides; PeptidesOrganisational unit
03861 - Bode, Jeffrey W. / Bode, Jeffrey W.
Funding
169451 - Protein Synthesis with Chemoselective Ligations (SNF)
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ETH Bibliography
yes
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