Murar Claudia E, Harmand Thibault J, Bode Jeffrey W
Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich, CH-8093 Zürich, Switzerland.
Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich, CH-8093 Zürich, Switzerland; Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya 464-8602, Japan.
Bioorg Med Chem. 2017 Sep 15;25(18):4996-5001. doi: 10.1016/j.bmc.2017.06.019. Epub 2017 Jun 15.
We describe a new route for the synthesis of (S)-N-Boc-5-oxaproline. This building block is a key element for the chemical synthesis of proteins with the α-ketoacid-hydroxylamine (KAHA) ligation. The new synthetic pathway to the enantiopure oxaproline is based on a chiral amine mediated enantioselective conjugate addition of a hydroxylamine to trans-4-oxo-2-butenoate. This route is practical, scalable and economical and provides decagram amounts of material for protein synthesis and conversion to other protected forms of (S)-oxaproline.
我们描述了一种合成(S)-N-Boc-5-氧代脯氨酸的新路线。该结构单元是通过α-酮酸-羟胺(KAHA)连接进行蛋白质化学合成的关键元素。这条对映体纯的氧代脯氨酸的新合成途径基于手性胺介导的羟胺对反式-4-氧代-2-丁烯酸酯的对映选择性共轭加成。该路线实用、可扩展且经济，可提供用于蛋白质合成以及转化为(S)-氧代脯氨酸其他保护形式的十克量的材料。
