Department of Chemistry, Colgate University, Hamilton, New York 13346, USA.
J Org Chem. 2013 Jul 5;78(13):6798-801. doi: 10.1021/jo401044x. Epub 2013 Jun 17.
The glycosylation of proteins, specifically installation of O-GlcNAc on Ser/Thr residues, is a dynamic control element for transcription repression, protein degradation, and nutrient sensing. To provide homogeneous and stable structures with this motif, the synthesis of a C-linked mimic, C-GlcNAc Ser, has been prepared from the C-Glc Ser by a double inversion strategy using azide to insert the C-2 nitrogen functionality. The C-Glc Ser was available by a ring-closing metathesis and hydroalkoxylation route.
蛋白质的糖基化，特别是在丝氨酸/苏氨酸残基上安装 O-GlcNAc，是转录抑制、蛋白质降解和营养感应的动态调控元件。为了提供具有这种基序的同质和稳定结构，已经通过使用叠氮化物插入 C-2 氮官能团的双反转策略，从 C-Glc 丝氨酸制备了 C-连接的类似物 C-GlcNAc 丝氨酸。C-Glc 丝氨酸可通过闭环复分解和氢烷氧基化路线获得。
