65577-21-1Relevant academic research and scientific papers
Synthesis of phosphonamidate peptides by Staudinger reactions of silylated phosphinic acids and esters
Wilkening, Ina,Signore, Giuseppe Del,Hackenberger, Christian P. R.
supporting information; experimental part, p. 349 - 351 (2011/03/17)
The Staudinger reaction of unprotected azido-peptides with silylated phosphinic acids and esters on the solid support offers a straightforward acid-free entry to different phosphonamidate peptide esters or acids under mild conditions in high purity and yield.
Synthesis and biological evaluation of phosphino dipeptide isostere inhibitor of human β-secretase (BACE1)
Manzenrieder, Florian,Frank, Andreas O.,Huber, Timo,Dorner-Ciossek, Cornelia,Kessler, Horst
, p. 4136 - 4143 (2008/03/11)
Phosphino dipeptide (PDP) isosteres are known to be useful analogues of the transition state of metalloprotease substrates. Here we describe the use of this unit for the design of aspartic protease inhibitors. A PDP analogue of OM00-3, a potent BACE1 inhibitor, was synthesized and exhibited high biological activity (IC50 ～ 12 nM).
Facile synthesis of bis-α-aminoalkylphosphinates
Drag, Marcin,Dlugosz, Katarzyna,Oleksyszyn, Jozef
, p. 2787 - 2795 (2007/10/03)
Herein we report a facile synthesis of esters of bis-α- aminoalkylphosphinic acids obtained by an addition of Cbz-protected phosphinic analogues of amino acid methyl esters to an appropriate imine in refluxing benzene. Complete deprotection of the esters
Synthesis of α1-(Cbz-aminoalkyl)-α2- (hydroxyalkyl)phosphinic esters
Drag, Marcin,Oleksyszyn, Józef
, p. 3359 - 3362 (2007/10/03)
A synthesis of α1-(Cbz-aminoalkyl)-α2- (hydroxyalkyl)phosphinic esters was achieved by the 1,2-addition of the appropriate aldehyde to Cbz-protected phosphinic analogues of amino acid esters in the presence of at least three equivale
A New Synthetic Route to 1-Aminoalkylphosphonous Acids
Grobelny, Damian
, p. 942 - 943 (2007/10/02)
The addition of bis(trimethylsilyl) phosphonite to N-(diphenylmethyl)imines 1 yields bis(trimethylsilyl) 1-(diphenylmethylamino)alkylphosphonites 2, which can be easily converted into 1-(diphenylmethylamino)alkylphosphonous acids 3 by treatment with aqueo
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.
