215608-32-5Relevant articles and documents
Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids
Zheng, Yongpeng,Xu, Jiaxi
, p. 5197 - 5206 (2014/07/08)
Enantiopure N-benzyloxycarbonyl-protected and free 3-substituted homotaurines were synthesized from naturally occurring amino acids via N-benzyloxycarbonyl protection, Arndt-Eistert homologation, reduction, esterification with thioacetic acid, and oxidation with performic acid. The current method is a convenient, practical, and salt-free method for the synthesis of enantiopure 3-substituted homotaurine with moderate to good yields.
Continuous flow synthesis of β-amino acids from α-amino acids via Arndt-Eistert homologation
Pinho, Vagner D.,Gutmann, Bernhard,Kappe, C. Oliver
, p. 37419 - 37422 (2014/12/09)
A fully continuous four step process for the preparation of β-amino acids from their corresponding α-amino acids utilizing the Arndt-Eistert homologation approach is described. the Partner Organisations 2014.
Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids
Zheng, Yongpeng,Xu, Jiaxi
, p. 5197 - 5206 (2014/12/10)
Enantiopure N-benzyloxycarbonyl-protected and free 3-substituted homotaurines were synthesized from naturally occurring amino acids via N-benzyloxycarbonyl protection, Arndt-Eistert homologation, reduction, esterification with thioacetic acid, and oxidation with performic acid. The current method is a convenient, practical, and salt-free method for the synthesis of enantiopure 3-substituted homotaurine with moderate to good yields.
MODULATORS OF HISTONE METHYLTRANSFERASE, AND METHODS OF USE THEREOF
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Page/Page column 171-172, (2012/06/30)
Disclosed are compounds, pharmaceutical compositions containing the compounds, and the uses of the compounds and compositions as modulators of histone methyltransferases, and for treating diseases influenced by modulation of histone methyltransferase activity.
Synthesis of novel N-protected β3-amino nitriles: study of their hydrolysis involving a nitrilase-catalyzed step
Veitia, Maite Sylla-Iyarreta,Brun, Pierre Louis,Jorda, Pierre,Falguieres, Annie,Ferroud, Clotilde
experimental part, p. 2077 - 2089 (2010/03/04)
Several commercially available nitrilases were investigated with regard to their potential to hydrolyze N-protected β3-amino nitriles into their corresponding N-protected β3-amino acids. The biotransformations were obtained in different proportions depending on the nitrilase involved. The best hydrolysis results were achieved for the N-Cbz-β3-amino nitrile from l-alanine using the NIT-107, in a phosphate buffer at 0.05 M. However, no biotransformation into the corresponding acids was observed for the N-sulfonylamide β3-amino nitriles. Two simple and efficient procedures to prepare the β3-amino nitriles from their analogous α-amino acids are described. Thirty four new substances were synthesized and characterized over the course of this work.
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.
Exceptionally simple homologation of protected α- to β-amino acids in the presence of silica gel
Koch, Karen,Podlech, Joachim
, p. 2789 - 2794 (2007/10/03)
The Wolff rearrangement of α-amino acid-derived diazoketones is simply achieved by gentle warming in a ethyl acetate/silica gel slurry containing catalytic amounts of silver trifluoroacetate. Without workup (not counting filtration and evaporation) the pr
Wolff rearrangement of Nα-Boc-/Z-protected aminodiazoketones to the corresponding β-amino acids under microwave irradiation
Kantharaju,Patil, Basanagoud S.,Suresh Babu, Vommina V.
, p. 2611 - 2613 (2007/10/03)
The Wolff rearrangement of Nα-Boc-/Z-protected aminodiazoketones in the presence of silver benzoate under microwave irradiation is described. The reaction is found to be rapid, efficient and complete. It results in the isolation of Boc-/Z- prot
Synthesis of new β-amino acids via 5-oxazolidinones and the arndt-eistert procedure
Hughes, Andrew B.,Sleebs, Brad E.
, p. 778 - 784 (2007/10/03)
N-Methyl β-amino acids are potentially useful amino acid derivatives for incorporation in lead peptide therapeutics. The syntheses of five such compounds are presented. Their synthesis via 6-oxazinanones was low yielding. Alternatively, reductive cleavage of a 5-oxazolidinone gave the N-methyl β-amino acid, which was then homologated via an Arndt-Eistert procedure in high yield to give the N-methyl α-amino acid. CSIRO 2005.
Peptidic aldehydes based on α- and β-amino acids: Synthesis, inhibition of m-Calpain, and anti-cataract properties
Payne, Richard J.,Brown, Karina M.,Coxon, James M.,Morton, James D.,Lee, Hannah Yun-Young,Abell, Andrew D.
, p. 877 - 884 (2007/10/03)
We present a new synthesis of SJA6017 (a potent m-calpain inhibitor) and its adaptation in order to prepare analogues in which the constituent Leu and Val residues are systematically replaced with their corresponding β-amino acids and/or the N-terminal fl
