核糖体P位点底物CCA-pcb的合成。

Synthesis of the ribosomal P-site substrate CCA-pcb.

作者信息

Zhong Minghong, Strobel Scott A

机构信息

Department of Molecular Biophysics and Biochemistry, Yale University, New Haven, Connecticut 06520-8114, USA.

出版信息

Org Lett. 2006 Jan 5;8(1):55-8. doi: 10.1021/ol052484f.

DOI:10.1021/ol052484f

PMID:16381566

Abstract

[reaction: see text] CCA-pcb (cytidylyl-(3'5')-cytidylyl-(3'5')-3'(2')-O-(N-(6-D-(+)-biotinoylaminohexanoyl)-L-phenylalanyl)adenosine), a ribosomal P-site substrate, was synthesized by phosphoramidite chemistry in 26 steps with an overall yield of 18%, starting from biotin. The synthesis relies on the judicious selection of orthogonal silyl protecting groups for the 5'-hydroxyls and acid-labile protecting groups (DMTr, AcE, and MeE) at other reactive sites to ensure the intactness of the labile ester. Both 3'-esterification and nucleotide coupling were accomplished by in situ activation with imidazolium ions.

摘要

[反应：见正文] CCA-pcb（胞苷酰基-(3′→5′)-胞苷酰基-(3′→5′)-3′(2′)-O-(N-(6-D-(+)-生物素酰氨基己酰基)-L-苯丙氨酰基)腺苷），一种核糖体P位点底物，从生物素开始，通过亚磷酰胺化学法经26步合成，总产率为18%。该合成依赖于为5′-羟基明智地选择正交硅基保护基团以及在其他反应位点选择酸不稳定保护基团（二甲氧三苯甲基、乙酰乙酯和甲基乙酯），以确保不稳定酯的完整性。3′-酯化和核苷酸偶联均通过用咪唑鎓离子原位活化来完成。