5962-91-4Relevant academic research and scientific papers
Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols
Inada, Haruki,Shibuya, Masatoshi,Yamamoto, Yoshihiko
supporting information, p. 709 - 713 (2019/01/25)
A practical telescoping three-step process for the syntheses of α-amino acids from the corresponding 1,2-diols has been developed. This process enables the direct synthesis of free α-amino acids without any protection/deprotection step. This method was also effective for the preparation of a 15N-labeled α-amino acid. 1,2-Diols bearing α,β-unsaturated ester moieties afforded bicyclic α-amino acids through intramolecular [3 + 2] cycloadditions. A preliminary study suggests that the resultant α-amino acids are resolvable by aminoacylases with almost complete selectivity.
Chemoselective conversion from α-hydroxy acids to α-keto acids enabled by nitroxyl-radical-catalyzed aerobic oxidation
Furukawa, Keisuke,Inada, Haruki,Shibuya, Masatoshi,Yamamoto, Yoshihiko
supporting information, p. 4230 - 4233 (2016/09/09)
The chemoselective oxidation of α-hydroxy acids to α-keto acids catalyzed by 2-azaadamantane N-oxyl (AZADO), a nitroxyl radical catalyst, is described. Although α-keto acids are labile and can easily release CO2 under oxidation conditions, the use of molecular oxygen as a cooxidant enables the desired chemoselective oxidation.
A chemoselective oxidation of monosubstituted ethylene glycol: Facile synthesis of optically active α-hydroxy acids
Chinthapally, Kiran,Baskaran, Sundarababu
, p. 4305 - 4309 (2014/06/23)
A mild and efficient method for the synthesis of optically active α-hydroxy acids through chemoselective oxidation of monosubstituted ethylene glycols using the TEMPO-NaOCl reagent system is described. It is evident from our studies that the solvent, pH and reaction temperature are very crucial for the success of this oxidation. The versatility of this method has been demonstrated with a variety of aliphatic, aromatic and carbohydrate substrates bearing various functional groups. the Partner Organisations 2014.
Novel approach to the synthesis of aliphatic and aromatic α-keto acids
Balducci, Daniele,Conway, Philip A.,Sapuppo, Giulia,Müller-Bunz, Helge,Paradisi, Francesca
experimental part, p. 7374 - 7379 (2012/09/10)
A new practical and efficient synthesis of α-keto acids was accomplished starting from the synthon 1,4-diacetylpiperazine-2,5-dione. The synthesis encompasses both aromatic and aliphatic substrates proving to be versatile and innovative with excellent carbon economy and recycling of the glycine by-product.
Enantioselective synthesis of non-natural amino acids using phenylalanine dehydrogenases modified by site-directed mutagenesis
Busca, Patricia,Paradisi, Francesca,Moynihan, Eamonn,Maguire, Anita R.,Engel, Paul C.
, p. 2684 - 2691 (2007/10/03)
The substrate scope of three mutants of phenylalanine dehydrogenase as biocatalysts for the transformation of a series of 2-oxo acids, structurally related to phenylpyruvic acid, to the analogous -amino acids, non-natural analogues of phenylalanine, has been investigated. The mutant enzymes are more tolerant than the wild type enzyme of the non-natural substrates, especially those with substituents at the 4-position on the phenyl ring. Excellent enantiocontrol resulted in all cases.
Potent, selective tetrahydro-β-carboline antagonists of the serotonin 2B (5HT(2B)) contractile receptor in the rat stomach fundus
Audia, James E.,Evrard, Deborah A.,Murdoch, Gwyn R.,Droste, James J.,Nissen, Jeffrey S.,Schenck, Kathy W.,Fludzinski, Pawel,Lucaites, Virginia L.,Nelson, David L.,Cohen, Marlene L.
, p. 2773 - 2780 (2007/10/03)
A series of potent, selective 5HT(2B) receptor antagonists has been identified based upon yohimbine, with SAR studies resulting in a 1000-fold increase in 5HT(2B) receptor affinity relative to the starting structure (- log K(B)s > 10.0 have been obtained). These high-affinity tetrahydro-β- carboline antagonists are able to discriminate among the 5HT2 family of serotonin receptors, with members of the series showing selectivities of more than 100-fold versus both the 5HT(2A) and 5HT(2C) receptors based upon radioligand binding and functional assays. As the first compounds reported with such selectivity and enhanced receptor affinity, these tetrahydro-β- carboline antagonists are useful tools for elucidating the role of serotonin acting at the 5HT(2B) receptor in normal and disease physiology.
The invention of radical reactions. Part XXXIV. Homologation of carboxylic acids to α-keto carboxylic acids by Barton-ester based radical chain chemistry
Barton, Derek H. R.,Chern, Ching-Yuh,Jaszberenyi, Joseph Cs.
, p. 1867 - 1886 (2007/10/02)
Carboxylic acids can be transformed into the homologous α-keto acids by Barton-ester based radical chemistry. The method was especially successful when ethyl α-trifluoroacetoxy acrylate was used as a radical trap.
Two Carbon Homologation of Carboxylic Acids via Carbon Radicals Generated from the Acyl Derivatives of N-Hydroxy-2-thiopyridone: Synthesis of Cn+2 α-Keto-acids from Cn Acids. (The 'Three carbon' Problem).
Barton, Derek H. R.,Chern, Ching-Yuh,Jaszberenyi, Joseph Cs.
, p. 5017 - 5020 (2007/10/02)
Reaction of olefins containing a three carbon atom chain with carbon radicals generated from carboxylic acids furnishes adducts that are precursors of the corresponding two carbon atom longer α-keto-acids.These keto-acids are furnished in high overall yield.
