287935-81-3

Upstream product

• 108327-37-3 [1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid 
• 115115-40-7 (R)-1-(N-benzyloxycarbonylamino)ethylphosphinic acid 
• 3070-71-1 methyl 2-benzylacrylate 
• 287935-86-8 methyl 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoate 

Downstream Products

• 287935-82-4 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine benzyl ester 
• 287935-83-5 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-3-iodotyrosine methyl ester 
• 287935-88-0 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-3-iodotyrosine 
• 287935-87-9 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine 
• 287935-84-6 2(S)-benzyl-3-[hydroxy(1'(R)-aminoethyl)phosphinyl]propanoyl-L-tyrosine 

Relevant academic research and scientific papers

Synthesis of 2(S)-benzyl-3-[hydroxy(1'(R)-amino ethyl)phosphinyl]propanoyl-L3-[125I]-iodotyrosine: A radiolabelled inhibitor of aminopeptidase N

2(S)-benzyl-3-[hydroxy(1'(R)-aminoethyl)phosphinyl]propanoyl-L-3-[125I]-iodo tyrosine was prepared from 1(R)-(N-benzyloxycarbonylamino)ethylphosphinic acid in a six step synthesis. This new iodinated compound, which is a highly efficient aminopeptidase N inhibitor (Ki = 0.95 nM), can be used for complete characterization of the biochemical and pharmacological properties of aminopeptidase N and its in vivo inhibition. A high radiochemical purity was obtained with a specific activity of 2.17 Ci/mmol at the end of the synthesis.

Design of the first highly potent and selective aminopeptidase N (EC 3.4.11.2) inhibitor

A series of phosphinic compounds mimicking the transition state of substrates hydrolysed by aminopeptidase N (EC 3.4.11.2) were synthesized. These new compounds have potent inhibitory activities with Ki values in the nanomolar range. These derivatives behave as the most potent APN inhibitors designed to date.