97206-19-4Relevant academic research and scientific papers
Discovery of Fluoromethylketone-Based Peptidomimetics as Covalent ATG4B (Autophagin-1) Inhibitors
Qiu, Zongxing,Kuhn, Bernd,Aebi, Johannes,Lin, Xianfeng,Ding, Haiyuan,Zhou, Zheng,Xu, Zhiheng,Xu, Danqing,Han, Li,Liu, Cheng,Qiu, Hongxia,Zhang, Yuxia,Haap, Wolfgang,Riemer, Claus,Stahl, Martin,Qin, Ning,Shen, Hong C.,Tang, Guozhi
supporting information, p. 802 - 806 (2016/08/24)
ATG4B or autophagin-1 is a cysteine protease that cleaves ATG8 family proteins. ATG4B plays essential roles in the autophagosome formation and the autophagy pathway. Herein we disclose the design and structural modifications of a series of fluoromethylketone (FMK)-based peptidomimetics as highly potent ATG4B inhibitors. Their structure-activity relationship (SAR) and protease selectivity are also discussed.
The preparation and alkylation of a butanedione-derived chiral glycine equivalent and its use for the synthesis of α-amino acids and α,α-disubstituted amino acids
Harding, Christopher I.,Dixon, Darren J.,Ley, Steven V.
, p. 7679 - 7692 (2007/10/03)
A benzyloxycarbonyl protected glycine equivalent 2 has been prepared in enantiopure form and has been used in the synthesis of both α-substituted amino acids and α,α-disubstituted amino acids. The process involved deprotonation to form the corresponding enolates which underwent stereoselective alkylation with various electrophiles and upon hydrolysis gave the corresponding amino acid derivatives as enantiomerically pure products.
Role of secondary structure in the asymmetric acylation reaction catalyzed by peptides based on chiral Cα-tetrasubstituted α-amino acids
Formaggio, Fernando,Barazza, Alessandra,Bertocco, Andrea,Toniolo, Claudio,Broxterman, Quirinus B.,Kaptein, Bernard,Brasola, Elena,Pengo, Paolo,Pasquato, Lucia,Scrimin, Paolo
, p. 3849 - 3856 (2007/10/03)
In a recent series of papers, Miller and co-workers were able to show that His(π-Me)-based, terminally protected peptides are potent catalysts of the asymmetric acyl transfer reaction, useful for the kinetic resolution of alcohols. In a structure-supporting solvent, one of the most active compounds, an Aib-containing tetrapeptide, is folded in a doubly intramolecularly H-bonded β-hairpin motif incorporating a type-II′ β-turn conformation. In this work, we have expanded the study of the Miller tetrapeptide by examining a set of analogues and shorter sequences (dipeptide amides), characterized by chiral Cα-tetrasubstituted α-amino acids of diverging bulkiness and optical configuration. Peptide synthesis in solution, conformational analysis by FT-IR absorption and 1H NMR techniques, and screening of catalytic activity as well have been performed. Our results confirm the close relationship between the β-hairpin 3D-structure and the catalytic activity of the peptides. A tetrapeptide analogue slightly more selective than the Miller compound has been found. However, the terminally protected, industrially more appealing, dipeptide amides are poorly effective.
A 2,3-butanedione protected chiral glycine equivalent--a new building block for the stereoselective synthesis of enantiopure N-protected alpha-amino acids.
Dixon, Darren J,Harding, Christopher I,Ley, Steven V,Tilbrook, D Matthew G
, p. 468 - 469 (2007/10/03)
A new chiral glycine equivalent 7 has been synthesised from glycidol using a chiral memory protocol, and its use in the synthesis of N-Z protected alpha-amino acids was demonstrated in a series of diasteroselective lithium enolate alkylation reactions and subsequent acid hydrolyses.
Synthesis of dipeptides containing α-substituted amino acids; their use as chiral ligands in Lewis-acid-catalyzed reactions
Kaptein, Bernard,Monaco, Vania,Broxterman, Quirinus B.,Schoemaker, Hans E.,Kamphuis, Johan
, p. 231 - 238 (2007/10/02)
L-α-Methylphenylalanine, obtained by enzymatic resolution of the corresponding racemic amide with amidase from Ochrobactrum anthropi NCIMB 40321, was used in the synthesis of dipeptides containing α-substituted amino acids.The 2-hydroxynaphthalene-1-carboxaldehyde Schiff bases of the dipeptides (1 and 2) were tested as Ti(IV) and Al(III) complexes in asymmetric Lewis-acid-catalyzed reactions.Only the Al(III) complex of 2 showed moderate enantioselectivity in the cyanation reaction of benzaldehyde with TMS-CN.
Process for preparation of alpha-alkyl amino acids
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, (2008/06/13)
A process for preparing α-alkyl amino acids by enantioretentive α-alkylation of α-amino acids is described. The products are bioactive compounds including some useful as therapeutic agents.
ENANTIORETENTIVE ALKYLATION OF ACYCLIC AMINO ACIDS
Karady, Sandor,Amato, Joseph S.,Weinstock, Leonard M.
, p. 4337 - 4340 (2007/10/02)
A stereospecific method is described for the alkylation of acyclic amino acids (alanine and phenylalanine) which proceeds with retention of configuration.The method involves a) conversion of the amino acid to the predominantly cis 2-aryl-3-carbobenzyloxy oxazolidinones (2 and 8), b) alkylation of the potassium enolate with CH3I or PhCH2Br, c) base hydrolysis and hydrogenolysis to afford the alkylated amino acid.
