25516-39-6Relevant academic research and scientific papers
Aziridine-2,3-dicarboxylic acid derivatives as inhibitors of papain
Schirmeister, Tanja
, p. 239 - 244 (1996)
Aziridine-2,3-dicarboxylates and N-acylated derivatives have been evaluated as potential irreversible inhibitors of the cysteine proteinase papain. Dependence of inhibition activity on stereochemistry of the aziridine moiety has been analyzed. Whereas unsubstituted (R,R)- and (S,S)-diethyl aziridine-2,3-dicarboxylates (5) and (2) show no significant difference in inactivation the derivative acylated with BOC-(S)-Phe (BOC-(S)-Phe-(S,S)-Azi) (10) shows a 6 fold higher activity than the diastereomer BOC-(S)-Phe-(R,R)-Azi (11). Analogs acylated with Z- or BOC-(S)-Ala (9, 8) have lower second-order rate constants, indicating binding of the amino acid moiety of the inhibitors to the S2 subsite of the enzyme.
Synthesis and solid-state conformations of 6S,8aR/S-6-alkyl-3,3-dimethyltetrahydrooxazolo[3,4-a]pyrazine-5,8-diones (Pseudo proline Diketopiperazines)
Beauchard, Anne,Dufton, Helen F.,Odumah, Kere,Jaggers, Rhian H.,Mahon, Mary F.,Wood, Pauline J.,Threadgill, Michael D.
, p. 11 - 24 (2018/09/14)
Peptide-like self-immolative molecular clips are required for release of active drugs from prodrugs by endopeptidases, generating diketopiperazines (DKPs) as by-products. Two diastereomeric series of cyclo-L-aminoacyl-R/S-dimethyloxazolidine carboxylate D
Efficient synthesis of conformationally constrained peptidomimetics containing 2-oxopiperazines
Pohlmann, Adriana,Schanen, Vincent,Guillaume, Dominique,Quirion, Jean-Charles,Husson, Henri-Philippe
, p. 1016 - 1022 (2007/10/03)
The enantioselective synthesis of a series of peptides containing the 3-substituted 2-oxopiperazine system is reported. The method involves a direct diastereoselective alkylation of the N-(hydroxyalkyl)-2-oxopiperazine 3, prepared in three steps from methyl L-leucinate in 38% yield, followed by oxidation of the hydroxyl function. Esterification of the resulting acids 11 and then deprotection and acylation of N-4 afforded tripeptide analogues 16 substituted by a large variety of alkyl side chains at the 3-position of the 2-oxopiperazine.
