Novel and facile solution-phase synthesis of 2,5-diketopiperazines and O-glycosylated analogs
Novel and facile solution-phase synthesis of 2,5-diketopiperazines and O-glycosylated analogs
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DOI：
10.1016/j.tet.2009.04.069
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发表时间：
2009-07-04
期刊：
影响因子：
2.1
通讯作者：
Carvalho, Ivone
中科院分区：
文献类型：
--
作者：
Campo, Vanessa L.;Martins, Maristela B.;Carvalho, Ivone
本工作描述了一系列具有潜在生物活性的相关二酮哌嗪类化合物的溶液合成：环（L-Pro-L-Ser）、环（L-Phe-L-Ser）、环（D-Phe-L-Ser）以及后者的相应糖基化类似物环[D-Phe-L-Ser（alpha GlcNAc）]和环[D-Phe-L-Ser（beta GlcNAc）]。该合成方法包括-OH或O-糖基化丝氨酸苄酯与NFmoc保护的氨基酸（Pro或Phe）的偶联反应，然后在20%哌啶的DMF溶液中进行一锅脱保护-环化反应。(C)2009爱思唯尔有限公司保留所有权利。
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.