91290-81-2Relevant academic research and scientific papers
Synthesis of phosphorus isosters of β-amyloid peptides fragments
Dmitriev,Ragulin
, p. 2091 - 2098 (2015/11/02)
We have developed a synthetic route to pseudo dipeptides, analogs of certain fragments of β-amyloid peptides (products of the APP protein hydrolysis). These compounds can be used for preparation of phosphinic acidic oligopeptides representing the peptide sequence of the β-amyloid but containing the phosphorus isoster peptide fragment. Synthesis of pseudo ornityl-glutamate, pseudo arginyl-glutamate, pseudo glycyl-leucine, and pseudo isoleucyl-glycine via amino- and amidoalkylation of phosphonic acids containing the structural isoster of the corresponding amino acid is described.
Pentanidium-catalyzed enantioselective phase-transfer conjugate addition reactions
Ma, Ting,Fu, Xiao,Kee, Choon Wee,Zong, Lili,Pan, Yuanhang,Huang, Kuo-Wei,Tan, Choon-Hong
supporting information; experimental part, p. 2828 - 2831 (2011/04/22)
A new chiral entity, pentanidium, has been shown to be an excellent chiral phase-transfer catalyst. The enantioselective Michael addition reactions of tert-butyl glycinate-benzophenone Schiff base with various α,β- unsaturated acceptors provide adducts with high enantioselectivities. A successful gram-scale experiment at a low catalyst loading of 0.05 mol % indicates the potential for practical applications of this methodology. Phosphoglycine ester analogues can also be utilized as the Michael donor, affording enantioenriched α-aminophosphonic acid derivatives and phosphonic analogues of (S)-proline.
Method of synthesis of phosphinic acids based on hypophosphites: VIII.1 synthesis of α-aminoalkylphenethylphosphinic acids
Dmitriev,Ragulin
body text, p. 1786 - 1791 (2012/01/12)
Development of methodology of double Arbuzov rearrangement based on hypophosphites allows a one-pot formation of two unsymmetrical phosphorus-carbon bonds by the Michael-Pudovik type reaction of stepwise addition of the intermediately forming silyl esters of trivalent phosphorus to different unsaturated compounds. A procedure was developed of the synthesis of α-aminoalkylphenethylphosphinic acids. Bis-(trimethylsilyl) phenethylphosphonite formed as a result of the addition of bis(trimethylsilyl) hypophosphite to styrene in situ was added without isolation from the reaction mixture to Schiff bases obtained preliminary from benzylamine or diphenylmethylamine and various aldehydes. The subsequent removal of N-protecting groups by hydrogenation or acidic hydrolysis gave a number of new α-aminoalkylphenethylphosphinic acids.
Synthesis of an α-aminophosphonate nucleoside as an inhibitor of S-adenosyl-L-homocysteine hydrolase
Steere, Jennifer A.,Sampson, Peter B.,Honek, John F.
, p. 457 - 460 (2007/10/03)
A phosphonic acid analogue of S-adenosyl-L-homocysteine was prepared by a novel method and the epimeric mixture separated. Preliminary studies indicate that each epimer causes time-dependent inactivation of S-adenosyl-L-homocysteine hydrolase, however each presented distinct kinetic characteristics.
1-Aminoalkylphosphonous Acids. Part 1. Isosteres of the Protein Amino Acids
Baylis, E. Keith,Campbell, Colin D.,Dingwall, John G.
, p. 2845 - 2853 (2007/10/02)
The synthesis of 1-aminoalkylphosphonous acids, isosteres of the protein amino acids, by addition of hypophosphorous acid to diphenylmethylimines is described.These analogues of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tyrosine, tryptophan, serine, threonine, methionine, cysteine, cystine, glutamic acid, lysine, ornithine, arginine, and proline have been prepared and the analogues of alanine, valine, leucine, phenylalanine, and methionine resolved.The alanine, valine and methionine analogues have interesting antimicrobial activity and the alanine analogue has plant growth inhibiting properties.Oxidation of the appropriate 1-aminoalkylphosphonous acids gave the 1-aminoalkylphosphonic acid analogues of (+/-)-alanine, (-)-alanine, (+/-)-valine, (-)-valine, (+/-)-serine, (+/-)-threonine, (+/-)-lysine, (-)-leucine, and (+/-)-ornithine.
