Diversity-oriented submonomer synthesis of azapeptides mediated by the Mitsunobu reaction
Diversity-oriented submonomer synthesis of azapeptides mediated by the Mitsunobu reaction
复制标题
Mitsunobu反应介导的氮杂肽的多样性导向的亚单体合成
DOI：
10.1039/c9qo00296k
复制
发表时间：
2019-07-21
影响因子：
5.4
通讯作者：
Zhang, Jinqiang
中科院分区：
文献类型：
--
作者：
Dai, Chuan;Ma, Jun;Zhang, Jinqiang
氮杂肽是一类肽类模拟物，在药物发现中具有重要的应用。由于联氨化学和多肽偶联的复杂性，以多样性为导向的氮杂肽合成具有挑战性。本文报道了一种改进的合成亚单体氮肽的方法，即在Mitsunobu反应的介导下，用各种醇选择性地将氨基脲烷基化。通过合成一系列血管紧张素1-7的azapeptidomimetics进一步证明了这一新策略的有效性。
Azapeptides represent a class of peptidomimetics and exhibit important utilizations in drug discovery. Diversity-oriented synthesis of azapeptides is challenging due to the complexity of hydrazine chemistry and peptide coupling. Here we report an improved procedure of submonomer azapeptide synthesis by selective alkylation of semicarbazone using various alcohols mediated by the Mitsunobu reaction. The effectiveness of this new strategy was further proved by synthesizing a series of azapeptidomimetics of angiotensin 1-7.