Next-Generation Paternò–Büchi Reagents for Lipid Analysis by Mass Spectrometry

化学 试剂 质谱法 色谱法 有机化学
作者
Jing Zhao,Xiaobo Xie,Qiaohong Lin,Xiaoxiao Ma,Pei Su,Yu Xia
出处
期刊:Analytical Chemistry [American Chemical Society]
卷期号:92 (19): 13470-13477 被引量:58
标识
DOI:10.1021/acs.analchem.0c02896
摘要

The Paternò-Büchi (PB) reaction is a photochemical reaction involving [2 + 2] cycloaddition between electronically excited carbonyl and carbon-carbon double bond (C═C). It has been established as a lipid derivatization strategy, leading to confident assignment of C═C locations in lipids when coupled with tandem mass spectrometry (MS/MS). Although acetone and several aryl-containing ketones or aldehydes have been explored as PB reagents, the chemical properties critical to achieving efficient conversion and minimum side reactions remain unclear. Herein, we investigated a set of acetophenone (AP) derivatives, aiming to provide insights into the development of new PB reagents with enhanced performance for lipid analysis. For AP derivatives, we found that electron-withdrawing groups (e.g., -F and -CF3) on the benzene ring improved the overall conversion, while a bulky group at the ortho-position decreased the conversion. Norrish Type I cleavage was largely diminished; however, the Norrish Type II side reaction was more competitive, producing products isomeric to the PB reaction products. Among all AP derivatives tested, 2',4',6'-trifluoroacetophenone (triFAP) showed the best performance. It offered a relatively high PB yield (20-30%) for different types of C═C, high sensitivity (sub-nM) for C═C identification, and accurate isomer quantitation. Due to the significantly reduced chemical interferences in shotgun analysis, triFAP provided better performance than that from acetone PB-MS/MS. An offline triFAP PB reaction was implemented in a liquid chromatography analysis workflow, which enabled the large-scale identification of phospholipids including C═C location isomers from a complex lipid extract.
最长约 10秒,即可获得该文献文件

科研通智能强力驱动
Strongly Powered by AbleSci AI
更新
PDF的下载单位、IP信息已删除 (2025-6-4)

科研通是完全免费的文献互助平台,具备全网最快的应助速度,最高的求助完成率。 对每一个文献求助,科研通都将尽心尽力,给求助人一个满意的交代。
实时播报
刚刚
刚刚
刚刚
刚刚
Rita发布了新的文献求助10
1秒前
1秒前
冷静凡天应助安静的缘分采纳,获得10
1秒前
Chief完成签到,获得积分0
2秒前
Wl0115发布了新的文献求助10
3秒前
3秒前
junkook发布了新的文献求助200
3秒前
不懈奋进应助纸抽盒采纳,获得200
3秒前
FYF发布了新的文献求助10
3秒前
大模型应助澡雪采纳,获得10
4秒前
彩色耳机发布了新的文献求助10
4秒前
4秒前
dhhaoyihong发布了新的文献求助10
6秒前
youyou发布了新的文献求助30
6秒前
7秒前
爱撞墙的猫完成签到,获得积分10
7秒前
8秒前
9秒前
fan发布了新的文献求助30
9秒前
9秒前
9秒前
10秒前
koko发布了新的文献求助30
11秒前
CodeCraft应助wenhao采纳,获得10
11秒前
12秒前
pyg发布了新的文献求助10
12秒前
量子星尘发布了新的文献求助10
12秒前
琪凯定理发布了新的文献求助10
13秒前
乐观的纸鹤完成签到,获得积分10
14秒前
努力学习的阿文完成签到 ,获得积分10
14秒前
15秒前
0526Test完成签到 ,获得积分10
15秒前
15秒前
15秒前
XiaoMing发布了新的文献求助10
15秒前
dylaner发布了新的文献求助10
16秒前
高分求助中
A new approach to the extrapolation of accelerated life test data 1000
Picture Books with Same-sex Parented Families: Unintentional Censorship 700
ACSM’s Guidelines for Exercise Testing and Prescription, 12th edition 500
Nucleophilic substitution in azasydnone-modified dinitroanisoles 500
不知道标题是什么 500
Indomethacinのヒトにおける経皮吸収 400
Phylogenetic study of the order Polydesmida (Myriapoda: Diplopoda) 370
热门求助领域 (近24小时)
化学 材料科学 医学 生物 工程类 有机化学 生物化学 物理 内科学 纳米技术 计算机科学 化学工程 复合材料 遗传学 基因 物理化学 催化作用 冶金 细胞生物学 免疫学
热门帖子
关注 科研通微信公众号,转发送积分 3976126
求助须知:如何正确求助?哪些是违规求助? 3520340
关于积分的说明 11202586
捐赠科研通 3256847
什么是DOI,文献DOI怎么找? 1798509
邀请新用户注册赠送积分活动 877645
科研通“疑难数据库(出版商)”最低求助积分说明 806516