109638-99-5

Upstream product

• 590-86-3 isovaleraldehyde 
• 65577-21-1 [1-[(diphenylmethyl)amino]-3-methylbutyl]phosphinic acid 
• 501-53-1 benzyl chloroformate 
• 80744-65-6 1-Amino-3-methyl-butylphosphonous acid 

Downstream Products

• 268225-01-0 2-benzyl-3-[(1-benzyloxycarbonylamino-3-methyl-butyl)-hydroxy-phosphinoyl]-propionic acid ethyl ester 
• 561007-53-2 methyl 3-{[1-(N-benzyloxycarbonylamino)-3-methylbutyl]hydroxyphosphinyl}propionate 
• 918329-97-2 methyl <1-<<(phenylmethoxy)carbonyl>amino>-3-methylbutyl>phosphinate 
• 615264-71-6 3-[(1-benzyloxycarbonylamino-3-methyl-butyl)-hydroxy-phosphinoyl]-propionic acid 
• 1019330-49-4 2-[(1-benzyloxycarbonylamino-3-methyl-butyl)-hydroxy-phosphinoylmethyl]-pent-4-ynoic acid ethyl ester 
• 109639-04-5 C₂₈H₃₉N₂O₇P 
• 109639-03-4 C₂₅H₄₁N₂O₇P 
• 109639-07-8 phenylmethyl N-<amino>-3-methylbutyl>phosphinyl>carbonyl>-L-leucinate 
• 109639-05-6 C₂₇H₃₇N₂O₇P 
• 109639-02-3 methyl N-<amino>-3-methylbutyl>phosphinyl>carbonyl>-L-leucinate 
• 109639-14-7 C₂₁H₃₃N₂O₇P 
• 109639-10-3 C₂₀H₃₁N₂O₇P 
• 234452-70-1 3-[(1-amino-3-methyl-butyl)-hydroxy-phosphinoyl]-2-benzyl-propionic acid 
• 268225-28-1 (S)-2-{2-Benzyl-3-[(1-benzyloxycarbonylamino-3-methyl-butyl)-hydroxy-phosphinoyl]-propionylamino}-3-phenyl-propionic acid 

Relevant academic research and scientific papers

Phosphinotripeptidic inhibitors of leucylaminopeptidases

Phosphinate pseudopeptide are analogs of peptides containing phosphinate moiety in a place of the amide bond. Due to this, the organophosphorus fragment resembles the tetrahedral transition state of the amide bond hydrolysis. Additionally, it is also capable of coordinating metal ions, for example, zinc or magnesium ions. These two properties of phosphinate pseudopeptides make them an ideal candidate for metal-related protease inhibitors. This research investigates the influence of additional residue in the P2 position on the inhibitory properties of phosphinopeptides. The synthetic strategy is proposed, based on retrosynthetic analysis. The N-C-P bond formation in the desired compounds is conveniently available from the three-component condensation of appropriate amino components, aldehydes, and hypophosphorous acid. One of the crucial synthetic steps is the careful selection of the protecting groups for all the functionals. Determination of the inhibitor activity of the obtained compounds has been done using UV-Vis spectroscopy and standard substrate L-Leu-p-nitroanilide toward the enzymes isolated from the porcine kidney (SsLAP, Sus scrofa Leucine aminopeptidase) and barley seeds (HvLAP, Hordeum vulgare Leucine aminopeptidase). An efficient procedure for the preparation of phosphinotripeptides has been performed. Activity test shown that introduction of additional residue into P2 position obtains the micromolar range inhibitors of SsLAP and HvLAP. Moreover, careful selection of the residue in the P2 position should improve its selectivity toward mammalian and plant leucyl aminopeptidases.

Synthesis of phosphonamidate peptides by Staudinger reactions of silylated phosphinic acids and esters

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)

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

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

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

1-Aminoalkylphosphonous Acids. Part 1. Isosteres of the Protein Amino Acids

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.