A Threonine-Forming Oxazetidine Amino Acid for the Chemical Synthesis of Proteins through KAHA Ligation.
Angew Chem Int Ed Engl
; 58(36): 12599-12603, 2019 09 02.
Article
em En
| MEDLINE
| ID: mdl-31260175
ABSTRACT
α-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 TIâ
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.
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Texto completo:
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Base de dados:
MEDLINE
Assunto principal:
Treonina
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Ubiquitina
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Enzimas de Conjugação de Ubiquitina
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Conectina
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Aminoácidos
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Hidroxilaminas
Idioma:
En
Ano de publicação:
2019
Tipo de documento:
Article