23632-67-9Relevant academic research and scientific papers
A NOVEL AND EFFICIENT SYNTHESIS OF L-VINYLGLYCINE
Hanessian, Stephen,Sahoo, Soumya P.
, p. 1425 - 1428 (1984)
A simple and practical synthesis of the title compound starting with L-glutamic acid is described.
Kras inhibitory cyclic peptide compound
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Paragraph 0362; 0656-0657, (2021/06/03)
The following were discovered: a cyclic peptide compound that interacts with Ras; and an unnatural amino acid that is useful in the production of said cyclic peptide compound. The cyclic peptide compound was also discovered to inhibit bonding between Ras and SOS. The following were additionally discovered: a specific unnatural amino acid included in said cyclic peptide compound; and a manufacturing method therefor.
PROCESSES FOR PREPARATION OF (S)-TERT-BUTYL 4,5-DIAMINO-5-OXOPENTANOATE
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, (2019/03/12)
Provided are processes for the preparation of (S)-tert-butyl 4,5-diamino-5-oxopentanoate, or a salt, solvate, hydrate, enantiomer, mixture of enantiomers, or isotopologue thereof. Also provided are solid forms of various intermediates and products obtained from the processes.
Versatile synthesis of the signaling peptide glorin
Barnett, Robert,Raszkowski, Daniel,Winckler, Thomas,Stallforth, Pierre
supporting information, p. 247 - 250 (2017/03/14)
We present a versatile synthesis of the eukaryotic signaling peptide glorin as well as glorinamide, a synthetic analog. The ability of these compounds to activate glorin-induced genes in the social amoeba Polysphondylium pallidum was evaluated by quantita
Synthesis of N -[(3 S)-2,6-dioxo-1-(2-phenylethyl)-3-piperidinyl]-(2 S)-2-methylbutanamide (( - )-julocrotine)
Silva, Luciano L.,Joussef, Antonio C.
, p. 1531 - 1534 (2011/08/21)
The total synthesis of ( - )-julocrotine (1) starting from l-glutamic acid in 41% overall yield is described. The methodology utilizes protection, deprotection, and regioselection (carbonyl differentiation via oxazolidinone) protocols, and glutarimide ring formation is the key step.
New developments for the design, synthesis and biological evaluation of potent SARS-CoV 3CLpro inhibitors
Regnier, Thomas,Sarma, Diganta,Hidaka, Koushi,Bacha, Usman,Freire, Ernesto,Hayashi, Yoshio,Kiso, Yoshiaki
scheme or table, p. 2722 - 2727 (2010/01/16)
A series of trifluoromethyl, benzothiazolyl or thiazolyl ketone-containing peptidic compounds as SARS-CoV 3CL protease inhibitors were developed and their potency was evaluated by in vitro protease inhibitory assays. Three candidates had encouraging resul
Constrained peptidomimetics reveal detailed geometric requirements of covalent prolyl oligopeptidase inhibitors
Lawandi, Janice,Toumieux, Sylvestre,Seyer, Valentine,Campbell, Philip,Thielges, Sabine,Juillerat-Jeanneret, Lucienne,Moitessier, Nicolas
experimental part, p. 6672 - 6684 (2010/04/28)
Prolyl oligopeptidases cleave peptides on the carboxy side of internal proline residues and their inhibition has potential in the treatment of human brain disorders. Using our docking program FITTED, we have designed a series of constrained covalent inhibitors, built from a series of bicyclic scaffolds, to study the optimal shape required for these small molecules. These structures bear nitrile functional groups that we predicted to covalently bind to the catalytic serine of the enzyme. Synthesis and biological assays using human brain-derived astrocytic cells and endothelial cells and human fibroblasts revealed that these compounds act as selective inhibitors of prolyl oligopeptidase activity compared to prolyl-dipeptidyl-aminopeptidase activity, are able to penetrate the cells and inhibit intracellular activities in intact living cells. This integrated computational and experimental study shed light on the binding mode of inhibitors in the enzyme active site and will guide the design of future drug-like molecules.
Synthesis of glutamic acid and glutamine peptides possessing a trifluoromethyl ketone group as SARS-CoV 3CL protease inhibitors
Sydnes, Magne O.,Hayashi, Yoshio,Sharma, Vinay K.,Hamada, Takashi,Bacha, Usman,Barrila, Jennifer,Freire, Ernesto,Kiso, Yoshiaki
, p. 8601 - 8609 (2007/10/03)
Trifluoromethyl-β-amino alcohol 11 [(4S)-tert-butyl 4-amino-6,6,6-trifluoro-5-hydroxyhexanoate] was synthesized in five steps starting from Cbz-l-Glu-OH 5 where the key step involved the introduction of the trifluoromethyl (CF3) group to oxazolidinone 7, resulting in the formation of silyl ether 8 [(4S,5S)-benzyl 4-(2-(tert-butoxycarbonyl)ethyl)-5-(trifluoromethyl)-5-(trimethylsilyloxy)oxazolidine-3-carboxylate]. Compound 11 was then converted into four tri- and tetra-glutamic acid and glutamine peptides (1-4) possessing a CF3-ketone group that exhibited inhibitory activity against severe acute respiratory syndrome coronavirus protease (SARS-CoV 3CLpro).
Effective methods for the synthesis of N-methyl β-amino acids from all twenty common α-amino acids using 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones
Hughes, Andrew B.,Sleebs, Brad E.
, p. 2611 - 2637 (2007/10/03)
N-Methyl β-amino acids are generally required for application in the synthesis of potentially bioactive modified peptides and other oligomers. Previous work highlighted the reductive cleavage of 1,3-oxazolidin-5-ones to synthesise N-methyl α-amino acids. Starting from α-amino acids, two approaches were used to prepare the corresponding N-methyl β-amino acids. First, α-amino acids were converted to N-methyl α-amino acids by the so-called '1,3-oxazolidin-5-one strategy', and these were then homologated by the Arndt-Eistert procedure to afford N-protected N-methyl β-amino acids derived from the 20 common α-amino acids. These compounds were prepared in yields of 23-57% (relative to N-methyl α-amino acid). In a second approach, twelve N-protected α-amino acids could be directly homologated by the Arndt-Eistert procedure, and the resulting β-amino acids were converted to the 1,3-oxazinan-6-ones in 30-45% yield. Finally, reductive cleavage afforded the desired N-methyl β-amino acids in 41-63% yield. One sterically congested β-amino acid, 3-methyl-3-aminobutanoic acid, did give a high yield (95%) of the 1,3-oxazinan-6-one (65), and subsequent reductive cleavage gave the corresponding AIBN-derived N-methyl β-amino acid 61 in 71% yield (Scheme 2). Thus, our protocols allow the ready preparation of all N-methyl β-amino acids derived from the 20 proteinogenic α-amino acids.
Nγ-Aryl glutamine analogues as probes of the ASCT2 neutral amino acid transporter binding site
Esslinger, C. Sean,Cybulski, Kimberly A.,Rhoderick, Joseph F.
, p. 1111 - 1118 (2007/10/03)
Analogues of l-glutamine were designed and synthesized to test a hydrogen-bond hypothesis between ligand and neutral amino acid transporter ASCT2. The key design feature contains a substituted phenyl ring on the amide nitrogen that contains electron withdrawing and electron donating groups that alter the pKa of the amide NH. Through this study a preliminary binding site map has been developed, and a potent commercially available competitive inhibitor of the ASCT2 transporter has been identified.
