期刊
TETRAHEDRON
卷 65, 期 27, 页码 5343-5349出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.04.069
关键词
Diketopiperazine; Dipeptide cyclization; Glycosylated amino acid; Solution-phase synthesis
资金
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP)
This work describes the synthesis in Solution of a series of related diketopiperazines with potential biological activities: cyclo(L-Pro-L-Ser), cyclo(L-Phe-L-Ser), cyclo(D-Phe-L-Ser) and the corresponding glycosylated analogs of the latter, cyclo[D-Phe-L-Ser(alpha GlcNAc)] and cyclo[D-Phe-L-Ser(beta GlcNAc)]. The synthetic approach involved coupling reactions of -OH or O-glycosylated serine benzyl esters with NFmoc-protected amino acids (Pro or Phe), followed by one-pot deprotection-cyclization reaction in the presence of 20% piperidine in DMF. (C) 2009 Elsevier Ltd. All rights reserved.
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