Ligation Product
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Synthesis ◽  
2019 ◽  
Vol 51 (05) ◽  
pp. 1273-1283 ◽  
Author(s):  
Simon Baldauf ◽  
Jeffrey Bode

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.


2018 ◽  
Vol 2018 (8) ◽  
pp. pdb.prot097865 ◽  
Author(s):  
Tae Hoon Kim ◽  
Job Dekker
Keyword(s):  

2015 ◽  
Vol 19 (1) ◽  
pp. 59-64 ◽  
Author(s):  
Lei Zhang ◽  
Jingjing Wang ◽  
Johann Roebelen ◽  
Anubhav Tripathi
Keyword(s):  

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