227804-34-4Relevant academic research and scientific papers
A Threonine-Forming Oxazetidine Amino Acid for the Chemical Synthesis of Proteins through KAHA Ligation
Baldauf, Simon,Schauenburg, Dominik,Bode, Jeffrey W.
, p. 12599 - 12603 (2019)
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 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.
CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines
Wang, Haoxuan,Yang, Jeffrey C.,Buchwald, Stephen L.
supporting information, p. 8428 - 8431 (2017/07/06)
This report details a general and enantioselective means for the synthesis of alkyl-substituted aziridines. This protocol offers a direct route for the synthesis of alkyl-substituted chiral aziridines from achiral starting materials. Readily accessed ally
An oxazetidine amino acid for chemical protein synthesis by rapid, serine-forming ligations
Pusterla, Ivano,Bode, Jeffrey W.
, p. 668 - 672 (2015/08/04)
Amide-forming ligation reactions allow the chemical synthesis of proteins by the union of unprotected peptide segments, and enable the preparation of protein derivatives not accessible by expression or bioengineering approaches. The native chemical ligati
Primary hydroxylamines and uses thereof
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Paragraph 0056; 0057; 0067, (2015/09/22)
The present invention relates to primary hydroxylamines, to pharmaceutical compositions comprising them, to their use in the treatment and/or prevention of bacterial infections and to their use in the prevention of formation or reduction of formed biofilm
Synthesis of Z-α,β-ethylenic N-boc-γ-amino esters from nitrones
Dagoneau, Christelle,Denis, Jean-No?l,Vallée, Yannick
, p. 602 - 604 (2007/10/03)
The reduction of γ-N-hydroxylamino-α,β-acetylenic esters bearing a methoxy-substituted benzyl group on the nitrogen atom by zinc in a MeOH/AcOH mixture leads stereoselectively to Z-γ-amino-α,β-ethylenic esters.
