Convenient synthesis of deuterium labelled sesquiterpenes

被引:10
作者
Duhamel, Nina [1 ]
Martin, Damian [2 ]
Larcher, Roberto [3 ]
Fedrizzi, Bruno [1 ]
Barker, David [1 ]
机构
[1] Univ Auckland, Sch Chem Sci, 23 Symonds St, Auckland, New Zealand
[2] New Zealand Inst Plant & Food Res Ltd, 85 Budge St, Marlborough 7240, New Zealand
[3] FEM IASMA Fdn Edmund Mach, Ist Agr San Michele Alladige, Via E Mach 1, I-38010 San Michele All Adige, TN, Italy
关键词
Sesquiterpenes; Isotopic labelling; Deuterium; Terpenoids; BAR SORPTIVE EXTRACTION; NATURAL SESQUITERPENOIDS; LIQUID DESORPTION; L; (+)-AROMADENDRENE; REARRANGEMENT; BIOSYNTHESIS; PROTEOMICS; VARIETIES; VOLATILES;
D O I
10.1016/j.tetlet.2016.08.079
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sesquiterpenes are an important class of molecules, with roles ranging from pollination and signalling to defense mechanisms. Despite their apparent importance, the limited number of commercial standards has hindered their study and precise quantification. Herein, we report the syntheses of fourteen labelled sesquiterpenes with a high level of deuterium incorporation (>95%) for applications in MS-based studies. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4496 / 4499
页数:4
相关论文
共 36 条
[1]   Acquired immunity to herbivory and allelopathy caused by airborne plant emissions [J].
Arimura, Gen-ichiro ;
Shiojiri, Kaori ;
Karban, Richard .
PHYTOCHEMISTRY, 2010, 71 (14-15) :1642-1649
[2]   OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].
BAL, BS ;
CHILDERS, WE ;
PINNICK, HW .
TETRAHEDRON, 1981, 37 (11) :2091-2096
[3]   Biogeneration of C13-norisoprenoid compounds:: experiments supportive for an apo-carotenoid pathway in grapevines [J].
Baumes, R ;
Wirth, J ;
Bureau, S ;
Gunata, Y ;
Razungles, A .
ANALYTICA CHIMICA ACTA, 2002, 458 (01) :3-14
[4]   Large emissions of sesquiterpenes and methyl chavicol quantified from branch enclosure measurements [J].
Bouvier-Brown, Nicole C. ;
Holzinger, Rupert ;
Palitzsch, Katrin ;
Goldstein, Allen H. .
ATMOSPHERIC ENVIRONMENT, 2009, 43 (02) :389-401
[5]   Isotope-labeled protein standards [J].
Brun, Virginie ;
Dupuis, Alain ;
Adrait, Annie ;
Marcellin, Marlene ;
Thomas, Damien ;
Court, Magali ;
Vandenesch, Francois ;
Garin, Jerome .
MOLECULAR & CELLULAR PROTEOMICS, 2007, 6 (12) :2139-2149
[6]   ENZYMATIC FORMATION OF SESQUITERPENES [J].
CANE, DE .
CHEMICAL REVIEWS, 1990, 90 (07) :1089-1103
[7]   Synthesis of Isotopically Labelled Oligoprenyl Diphosphates and Their Application in Mechanistic Investigations of Terpene Cyclases [J].
Citron, Christian A. ;
Rabe, Patrick ;
Barra, Lena ;
Nakano, Chiaki ;
Hoshino, Tsutomu ;
Dickschat, Jeroen S. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (34) :7684-7691
[8]   Quantification approach for assessment of sparkling wine volatiles from different soils, ripening stages, and varieties by stir bar sorptive extraction with liquid desorption [J].
Coelho, Elisabete ;
Coimbra, Manuel A. ;
Nogueira, J. M. F. ;
Rocha, Silvia M. .
ANALYTICA CHIMICA ACTA, 2009, 635 (02) :214-221
[9]   Optimisation of stir bar sorptive extraction and liquid desorption combined with large volume injection-gas chromatography-quadrupole mass spectrometry for the determination of volatile compounds in wines [J].
Coelho, Elisabete ;
Perestrelo, Rosa ;
Neng, Nuno R. ;
Camara, Jose S. ;
Coimbra, Manuel A. ;
Nogueira, J. M. F. ;
Rocha, Silvia M. .
ANALYTICA CHIMICA ACTA, 2008, 624 (01) :79-89
[10]  
D'Onofrio C., 2006, 9 INT C GRAP GEN BRE, V827, P331