473907-77-6

Upstream product

• 139109-23-2 (4R,5S)-1,5-dimethyl-4-phenyl-3-(2-propenoyl)-2-imidazolidinone 
• 18791-02-1 2,3-dibromo-propionyl chloride 
• 92841-65-1 (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one 

Downstream Products

• 199122-48-0 (4R,5S,2'R)-1,5-dimethyl-3-[(2'-aziridinyl)carbonyl]-4-phenylimidazolidin-2-one 
• 473907-82-3 (4'''R,5'''S)-5'-deoxy-5'-{[2''-carboxyl-(1''',5'''-dimethyl-4'''-phenylimidazolidin-2'''-one)]aziridino}-2',3'-bis(O-triethylsilyl)adenosine 
• 473907-81-2 (4'''R,5'''S)-5'-deoxy-5'-{[2''-carboxyl-(1''',5'''-dimethyl-4'''-phenylimidazolidin-2'''-one)]aziridino}-2',3'-bis(O-triethylsilyl)adenosine 
• 260784-00-7 (4R,5S,2'R,2''S)-1,5-dimethyl-3-[3'-(2''-acetamido-4''-methylpentanoyl)amino-2'-hydroxypropionyl]-4-phenylimidazolidin-2-one 
• 260783-99-1 (5R,4'R,5'S,1''S)-4,5-dihydro-2-(1''-acetamido-3''-methyl-1''-butyl)-5-[(1',5'-dimethyl-4'-phenylimidazolidin-2'-on-3'-yl)carbonyl]oxazole 
• 260783-98-0 (4R,5S,2'R,2''S)-1,5-dimethyl-3-{[1'-(2''-acetamido-4''-methylpentanoyl)-2'-aziridinyl]carbonyl}-4-phenylimidazolidin-2-one 
• 92841-65-1 (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one 

Relevant academic research and scientific papers

Expeditious synthesis of aziridine-based cofactor mimics

S-Adenosyl-L-methionine mimics were synthesized in a linear fashion highlighting methodology that bypasses the need for adenine base protection. These aziridine-based cofactor mimics are envisioned as useful biochemical tools and potential therapeutic agents whose mechanism of action hinges upon aberrant methyltransferase enzymes. Aziridination of the 5′ position of adenosine was effected by convergence of suitably protected 5′-aminoadenosine with various dibromopropionates. The economy and high yields for this route to said aziridine-based cofactors is highly amenable to large-scale chemistry which no doubt will be vital to their development as therapeutics and biochemical tools.

Dipeptides containing D-serine or D-isoserine from the same (R)-aziridine-2-imide by a simple reversal of the synthetic procedure

The ring expansion of 3-unsubstituted (R)-aziridine-2-imide- containing dipeptide under acidic conditions gives rise to oxazoline-5-imide regio and stereoselectively, which can be hydrolysed to the dipeptide containing D-isoserine. On the other hand, the ring opening of 3-unsubstituted (R)-aziridine-2-ester dipeptide, easily obtained from the same (R)-aziridine, gives the regioisomeric dipeptide containing D-serine.