407618-87-5Relevant academic research and scientific papers
Piperazine-2,3,5-triones in the synthesis of constrained peptides
Bailey, Patrick D.,Boa, Andrew N.,Baker, S. Richard,Clayson, Joanne,Murray, Ernest J.,Rosair, Georgina M.
, p. 7557 - 7560 (1999)
Amino acid amides react with diethyl oxalate and sodium ethoxide to yield 6-substituted piperazine-2,3,5-triones, which can be mono-alkylated at N4, bis-alkylated at N4 and C6, or tris-alkylated at N4, N1, and C6 under mild basic conditions; this provides access to i) α,α-disubstituted cyclic peptide derivatives; ii) constrained peptides via C(α)-N bond formation; iii) DKP analogues.
Synthesis of conformationally constrained amino acid and peptide derivatives
Bailey,Bannister,Bernad,Blanchard,Boa
, p. 3245 - 3251 (2007/10/03)
6-Benzylpiperazine-2,3,5-trione 5, a cyclic phenylalanine derivative, can be selectively and sequentially alkylated at N4, C6 and N1 to provide a range of conformationally constrained phenylalanine mimetics. Alkylation at C6, the α-carbon of the phenylalanine moiety is achieved under mild conditions and gives rise to Phe derivatives posessing a dialkylated α-carbon. Alkylation of piperazine 5 using methyl bromoacetate and ethyl bromopropionate gives access to peptoids 7 and 21 which are conformationally contrained Phe-Gly and Phe-Ala analogues respectively. The X-ray crystal structure of triallylated derivative 17 is also reported.
