Pinpointing Double Bonds in Lipids by Paterno-Buchi Reactions and Mass Spectrometry

被引:271
作者
Ma, Xiaoxiao [1 ]
Xia, Yu [1 ]
机构
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
基金
美国国家科学基金会;
关键词
double bond location; Patern-Buchi reaction; photochemical reactions; tandem mass spectrometry; unsaturated lipids; OZONE-INDUCED DISSOCIATION; UNSATURATED FATTY-ACIDS; ELECTROSPRAY-IONIZATION; THERMAL-DECOMPOSITION; SHOTGUN LIPIDOMICS; POSITION; ESTERS; DERIVATIVES; DIFFERENTIATION; LOCATION;
D O I
10.1002/anie.201310699
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The positions of double bonds in lipids play critical roles in their biochemical and biophysical properties. In this study, by coupling Patern-Buchi (P-B) reaction with tandem mass spectrometry, we developed a novel method that can achieve confident, fast, and sensitive determination of double bond locations within various types of lipids. The P-B reaction is facilitated by UV irradiation of a nanoelectrospray plume entraining lipids and acetone. Tandem mass spectrometry of the on-line reaction products via collision activation leads to the rupture of oxetane rings and the formation of diagnostic ions specific to the double bond location.
引用
收藏
页码:2592 / 2596
页数:5
相关论文
共 36 条
[1]   Recent progress regarding regio-, site-, and stereoselective formation of oxetanes in Paterno-Buchi reactions [J].
Abe, Manabu .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2008, 55 (03) :479-486
[2]   Hydroxy-directed regio- and diastereoselective [2+2] photocycloaddition (Paterno-Buchi reaction) of benzophenone to chiral allylic alcohols [J].
Adam, W ;
Peters, K ;
Peters, EM ;
Stegmann, VR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (12) :2958-2959
[3]  
[Anonymous], 2011, ANGEW CHEM INT ED, V50, P8275
[4]   Advances in Mass Spectrometry for Lipidomics [J].
Blanksby, Stephen J. ;
Mitchell, Todd W. .
ANNUAL REVIEW OF ANALYTICAL CHEMISTRY, VOL 3, 2010, 3 :433-465
[5]   Analysis of unsaturated lipids by ozone-induced dissociation [J].
Brown, Simon H. J. ;
Mitchell, Todd W. ;
Blanksby, Stephen J. .
BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR AND CELL BIOLOGY OF LIPIDS, 2011, 1811 (11) :807-817
[6]   LIGHT-CATALYZED ORGANIC REACTIONS .1. THE REACTION OF CARBONYL COMPOUNDS WITH 2-METHYL-2-BUTENE IN THE PRESENCE OF ULTRAVIOLET LIGHT [J].
BUCHI, G ;
INMAN, CG ;
LIPINSKY, ES .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (17) :4327-4331
[7]   DETERMINATION OF DOUBLE-BOND POSITION IN MONOUNSATURATED ACETATES BY MASS-SPECTROMETRY OF DIMETHYL DISULFIDE ADDUCTS [J].
BUSER, HR ;
ARN, H ;
GUERIN, P ;
RAUSCHER, S .
ANALYTICAL CHEMISTRY, 1983, 55 (06) :818-822
[8]   DETERMINATION OF DOUBLE-BOND POSITION IN MONOUNSATURATED FATTY-ACIDS BY MASS ANALYZED ION KINETIC-ENERGY SPECTROMETRY COLLISION-INDUCED DISSOCIATION AFTER CHEMICAL IONIZATION OF THEIR AMINO ALCOHOL DERIVATIVES [J].
CERVILLA, M ;
PUZO, G .
ANALYTICAL CHEMISTRY, 1983, 55 (13) :2100-2103
[9]   Using ambient ozone for assignment of double bond position in unsaturated lipids [J].
Ellis, Shane R. ;
Hughes, Jessica R. ;
Mitchell, Todd W. ;
Panhuis, Marc In Het ;
Blanksby, Stephen J. .
ANALYST, 2012, 137 (05) :1100-1110