通过连接方法确定结构：结合合成方法与核磁共振、红外光谱以及振动圆二色光谱法来测定hemicalide中的相对构型。

Strength by joining methods: combining synthesis with NMR, IR, and vibrational circular dichroism spectroscopy for the determination of the relative configuration in hemicalide.

作者信息

De Gussem Ewoud, Herrebout Wouter, Specklin Simon, Meyer Christophe, Cossy Janine, Bultinck Patrick

机构信息

Department of Inorganic and Physical Chemistry, Ghent University, Krijgslaan 281-S3, 9000 Ghent (Belgium); Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp (Belgium).

出版信息

Chemistry. 2014 Dec 22;20(52):17385-94. doi: 10.1002/chem.201404822. Epub 2014 Oct 24.

DOI:10.1002/chem.201404822

PMID:25346258

Abstract

The relative configuration of a key subunit of hemicalide, a recently isolated, highly bioactive marine natural product having potent antiproliferative activity against a panel of human cancer cell lines, was assigned by combining stereocontrolled synthesis of model substrates with NMR, IR, and vibrational circular dichroism (VCD) spectroscopy. The assignment of the absolute configuration of asymmetric carbon center C42 in two structurally complex epimeric substructures containing six stereocenters by VCD analysis illustrates the power and reliability of combining methods.

摘要

海环肽是一种最近分离出的具有高生物活性的海洋天然产物，对一组人类癌细胞系具有强大的抗增殖活性。通过将模型底物的立体控制合成与核磁共振（NMR）、红外光谱（IR）和振动圆二色光谱（VCD）相结合，确定了海环肽关键亚基的相对构型。通过VCD分析确定了两个含有六个立体中心的结构复杂的差向异构亚结构中不对称碳中心C42的绝对构型，这说明了组合方法的有效性和可靠性。