Fluorogenic probes for chemical transformations: 9-anthracene derivatives for monitoring reaction progress by an increase in fluorescence

被引：13

作者：

Mase, Nobuyuki ^{[1
,2
,3
]}

Takabe, Kunihiko ^{[3
]}

Tanaka, Fujie ^{[4
,5
]}

机构：

[1] Shizuoka Univ, Dept Appl Chem & Biochem Engn, Fac Engn, Hamamatsu, Shizuoka 4328561, Japan

[2] Shizuoka Univ, Green Energy Res Div, Res Inst Green Sci & Technol, Hamamatsu, Shizuoka 4328561, Japan

[3] Shizuoka Univ, Dept Mol Sci, Fac Engn, Hamamatsu, Shizuoka 4328561, Japan

[4] Grad Univ, Okinawa Inst Sci & Technol, Okinawa 9040495, Japan

[5] Grad Univ, Okinawa Inst Sci & Technol, Kyoto 6020841, Japan

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 32期

基金：

日本学术振兴会;

关键词：

Fluorogenic probe; Fluorescent molecules; High-throughput screening; Carbon-carbon bond formation; Reaction sensor; TURN-ON PROBE; ALDOL REACTIONS; ALDEHYDE; ENZYMES; PROTEIN; ACTIVATION; SUBSTRATE; BONDS; SPECIFICITY; CHEMISTRY;

D O I：

10.1016/j.tetlet.2013.06.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The development of fluorogenic probes for chemical transformations bearing anthracene as a fluorescent core moiety is reported. Fluorogenic probes were designed by linking anthracene with functional groups used for reactions of interest. Each fluorogenic probe, possessing a reaction group such as aldehyde, alpha,beta-unsaturated ketone, or imine at the 9-position of the anthracene, showed no or very low fluorescence. Reaction products of the probes, including aldol and addition products, were highly fluorescent. The products showed more than 1000-fold higher fluorescence than did the fluorogenic probes under the same conditions. The utility of the fluorogenic probes was demonstrated in monitoring the progress of a catalyzed aldol reaction. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：4306 / 4308

页数：3

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