Synthesis and Evaluation of Cyclic Acetals of Serine Hydroxylamine for Amide-Forming KAHA Ligations
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Author / Producer
Date
2019-03-01
Publication Type
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.
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Publication status
published
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Editor
Book title
Journal / series
Volume
51 (5)
Pages / Article No.
1273 - 1283
Publisher
Thieme
Event
Edition / version
Methods
Software
Geographic location
Date collected
Date created
Subject
Ligation; Hydroxylamines; Acetals; Amides; Peptides
Organisational unit
03861 - Bode, Jeffrey W. / Bode, Jeffrey W.
Notes
Funding
169451 - Protein Synthesis with Chemoselective Ligations (SNF)