A Threonine-Forming Oxazetidine Amino Acid for the Chemical Synthesis of Proteins through KAHA Ligation

被引:11
|
作者
Baldauf, Simon [1 ]
Schauenburg, Dominik [1 ]
Bode, Jeffrey W. [1 ,2 ]
机构
[1] Swiss Fed Inst Technol, Dept Chem & Appl Biosci, Lab Organ Chem, Wolfgang Pauli Str 10, CH-8093 Zurich, Switzerland
[2] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Nagoya, Aichi 4648602, Japan
基金
瑞士国家科学基金会;
关键词
amides; hydroxylamines; ligation; peptides; proteins; UBIQUITIN-CONJUGATING ENZYMES; STAUDINGER LIGATION; POLYUBIQUITINATION; PEPTIDE; FAMILY; SERINE; DOMAIN;
D O I
10.1002/anie.201906486
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
alpha-Ketoacid-hydroxylamine (KAHA) ligation allows the coupling of unprotected peptide segments through the chemoselective formation of an amide bond. Currently, the most widely used variant employs a 5-membered cyclic hydroxylamine that forms a homoserine ester as the primary ligation product. In order to directly form amide-linked threonine residues at the ligation site, we prepared a new 4-membered cyclic hydroxylamine building block. This monomer was applied to the synthesis of wild-type ubiquitin-conjugating enzyme UbcH5a (146 residues) and Titin protein domain TI I27 (89 residues). Both the resulting UbcH5a and the variant with two homoserine residues showed identical activity to a recombinant variant in a ubiquitination assay.
引用
收藏
页码:12599 / 12603
页数:5
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