Synthesis of azide-fluoro-dehydrocoelenterazine analog as a photoaffinity-labeling probe and photolysis of azide-fluoro-coelenterazine

被引：20

作者：

Kuse, M

Doi, I

Kondo, N

Kageyama, Y

Isobe, M ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Bioagr Sci, Organ Chem Lab, Nagoya, Aichi 4648601, Japan

[2] Nagoya Univ, Chem Instrument Div, RCMS, Chikusa Ku, Nagoya, Aichi 4648602, Japan

来源：

TETRAHEDRON | 2005年 / 61卷 / 24期

基金：

日本学术振兴会;

关键词：

coelenterazine; deuteriation MS; exchangeable protons; azide-fluoro-phenyl; photoaffinity probe;

D O I：

10.1016/j.tet.2005.04.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A photosensitive azide-fluoro-dehydrocoelenterazine analog (Az-F-DCT) was synthesized, starting from 4-fluorophenylacetic acid, as a photoaffinity-labeling probe in order to analyze symplectin active site. To examine the photo-reactivity of Az-F-DCT, azide-fluoro-coelenterazine analog (Az-F-CT) was used as a potent symplectin chromophore model. Photolysis of Az-F-CT in 2,2,2-trifluoroethanol afforded nitrene intermediate to give an insertion product. The structure of this product was confirmed through spectroscopic analyses particularly by using a proton/deuterium (H/D) exchange experiments with ESI-Q-TOF-MS and -MS/MS measurement. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：5754 / 5762

页数：9

共 26 条

[1] Using photolabile ligands in drug discovery and development [J].