Piperazine-2,3,5-triones in the synthesis of constrained peptides

✍ Scribed by Patrick D. Bailey; Andrew N. Boa; S.Richard Baker; Joanne Clayson; Ernest J. Murray; Georgina M. Rosair

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 251 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)01602-0

✦ Synopsis

Amino acid amides react with diethyl oxalate and sodium ethoxide to yield 6-substituted piperazine-2,3,5triones, which can be mono-alkylated at N 4, bis-alkylated at N 4 and C 6, or tris-alkylated at N 4, N 1, and C 6 under mild basic conditions; this provides access to i) ct,a-disubstituted cyclic peptide derivatives; ii) constrained peptides v/a C(ct)-N bond formation; iii) DKP analogues.