Nielsen Thomas E, Le Quement Sebastian, Meldal Morten
Carlsberg Laboratory, SPOCC Centre, Gamle Carlsberg Vej 10, DK-2500 Valby, Denmark.
Org Lett. 2005 Aug 18;7(17):3601-4. doi: 10.1021/ol050871j.
A general strategy for the solid-phase synthesis of structurally diverse bicyclic dipeptide mimetics is presented. Depending on the amino acid side-chain (R(1)), peptide-derived N-acyliminium intermediates may undergo nucleophilic attack from either side-chain functional groups (-OH, -NH(2), -SH, and -CONH(2)) or the amide backbone (-CONH-) of the peptide, thus affording a range of aza-, thia-, and oxabicycloalkanes in excellent purity and diastereoselectivity. [reaction: see text]
本文提出了一种用于固相合成结构多样的双环二肽模拟物的通用策略。根据氨基酸侧链（R(1)）的不同，肽衍生的N-酰基亚胺离子中间体可能会受到来自肽的侧链官能团（-OH、-NH(2)、-SH和-CONH(2)）或酰胺主链（-CONH-）的亲核攻击，从而以优异的纯度和非对映选择性得到一系列氮杂、硫杂和氧杂双环烷烃。[反应：见正文]
