Department of Chemistry, Birla Institute of Technology and Science, Pilani 333031, Rajasthan, India.
Chemistry Division, Nyro Research India, Kochi 682021, Kerala, India.
J Org Chem. 2020 Oct 2;85(19):12147-12159. doi: 10.1021/acs.joc.0c01319. Epub 2020 Sep 16.
A smooth traceless ligation strategy using an air-stable phosphane probe (2-(diphenylphosphanyl)phenyl)methanol as a C-terminus activator has been demonstrated at simple and sterically hindered amino acid junctions (Gly, Ala, Trp, Glu). This Staudinger peptide ligation proceeds via formation of a seven-membered transition state to afford di-, tetra-, and pentapeptides in 78-95% yields. The experimental results of ligation at Gly junction and regioselective ligation at Glu junction were theoretically studied by computational calculations. These findings established the versatile behavior of our synthesized phosphane probe for Staudinger peptide ligation toward synthesizing peptides and proteins of choice.
已经证明，使用稳定的膦探针（2-（二苯基膦基）苯甲醇）作为 C 末端激活剂的无痕平滑连接策略，可以在简单和位阻氨基酸连接处（甘氨酸、丙氨酸、色氨酸、谷氨酸）进行。这种施蒂德inger 肽连接通过形成一个七元过渡态进行，以 78-95%的产率得到二肽、四肽和五肽。通过计算计算对甘氨酸连接处的连接实验结果和谷氨酸连接处的区域选择性连接进行了理论研究。这些发现确立了我们合成的膦探针在 Staudinger 肽连接中用于合成所需肽和蛋白质的多功能行为。
