Synthesis of cyclic peptide hemicryptophanes: enantioselective recognition of a chiral zwitterionic guest
Synthesis of cyclic peptide hemicryptophanes: enantioselective recognition of a chiral zwitterionic guest
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DOI：
10.1039/c3cc44784g
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发表时间：
2013-01-01
影响因子：
4.9
通讯作者：
Hutton, Craig A.
中科院分区：
文献类型：
--
作者：
Cochrane, James R.;Schmitt, Aline;Hutton, Craig A.
描述了一类新的含环肽的半隐烷的第一成员的合成。通过将藜芦基基团连接到环状六肽c（YG）（3）的L-酪氨酸侧链上，然后通过分子内环化脱水生成CTV单元来实现合成。以2：1的比例产生非对映异构的P-和M-半隐烷，并通过色谱法分离。通过与肉毒碱的络合反应研究了半隐烷的对映选择性结合性质。发现两种异构体对结合（R）-肉毒碱具有显著的选择性。
The synthesis of the first members of a new class of cyclic peptide-containing hemicryptophanes is described. Synthesis was achieved through attachment of veratryl groups to the L-tyrosine side chains of a cyclic hexapeptide, c(YG)(3), followed by intramolecular cyclodehydration to generate the CTV unit. The diastereomeric P- and M-hemicryptophanes were generated in a 2 : 1 ratio and were separated by chromatography. The enantioselective binding properties of the hemicryptophanes were investigated by complexation with carnitine. Both isomers were found to have significant selectivity for binding (R)-carnitine.