Journal
TETRAHEDRON
Volume 58, Issue 42, Pages 8515-8523Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(02)01021-9
Keywords
combinatorial chemistry; piperazine-2,5-diones; 2,5-dioxopiperazines; cyclopeptide; peptidomimetic; racemization
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Twenty-four bifunctional diketopiperazines, cyclo(-Aax-Bbx-) consisting of glutamic or aspartic acid (Aax) and lysine, ornithine or diaminobutyric (Dab) acid (Bbx) were synthesized. D-Dab moiety was incorporated as D-Gln followed by Hoffman-type rearrangement induced by Phl[OC(O)CF3](2.) Cyclization conditions for the related linear dipeptide precursors allowing racemization to be kept at a minimum were determined. (C) 2002 Elsevier Science Ltd. All rights reserved.
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