Grunhaus Dana, Molina Estefanía Rossich, Cohen Roni, Stein Tamar, Friedler Assaf, Hurevich Mattan
The Institute of Chemistry, The Hebrew University of Jerusalem, Edmond J. Safra Campus, Givat Ram, Jerusalem, 91904, Israel.
Org Process Res Dev. 2022 Aug 19;26(8):2492-2497. doi: 10.1021/acs.oprd.2c00164. Epub 2022 Jul 12.
Preparing phosphorylated peptides with multiple adjacent phosphorylations is synthetically difficult, leads to β-elimination, results in low yields, and is extremely slow. We combined synthetic chemical methodologies with computational studies and engineering approaches to develop a strategy that takes advantage of fast stirring, high temperature, and a very low concentration of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to produce multiphosphorylated peptides at an extremely rapid time and high purity.
制备具有多个相邻磷酸化位点的磷酸化肽在合成上具有难度,会导致β-消除反应,产率低且速度极慢。我们将合成化学方法与计算研究及工程方法相结合,开发出一种策略,该策略利用快速搅拌、高温以及极低浓度的1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU),能在极短时间内以高纯度制备多磷酸化肽。