Artículo
Salum, M.L.; Itovich, L.M.; Erra-Balsells, R. "Z-sinapinic acid: The change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI-MS analysis" (2013) Journal of Mass Spectrometry. 48(11):1160-1169
Consulte la política de Acceso Abierto del editor
Abstract:
Successful application of matrix-assisted laser desorption/ionization (MALDI) MS started with the introduction of efficient matrices such as cinnamic acid derivatives (i.e. 3,5-dimethoxy-4-hydroxycinnamic acid, SA; α-cyano-4-hydroxycinnamic acid). Since the empirical founding of these matrices, other commercial available cinnamic acids with different nature and location of substituents at benzene ring were attempted. Rational design and synthesis of new cinnamic acids have been recently described too. Because the presence of a rigid double bond in its molecule structure, cinnamic acids can exist as two different geometric isomers, the E-form and Z-form. Commercial available cinnamic acids currently used as matrices are the geometric isomers trans or E (E-cinnamic and trans-cinnamic acids). As a new rational design of MALDI matrices, Z-cinnamic acids were synthesized, and their properties as matrices were studied. Their performance was compared with that of the corresponding E-isomer and classical crystalline matrices (3,5-dihydroxybenzoic acid; norharmane) in the analysis of neutral/sulfated carbohydrates. Herein, we demonstrate the outstanding performance for Z-SA. Sulfated oligosaccharides were detected in negative ion mode, and the dissociation of sulfate groups was almost suppressed. Additionally, to better understand the quite different performance of each geometric isomer as matrix, the physical and morphological properties as well as the photochemical stability in solid state were studied. The influence of the E/Z photoisomerization of the matrix during MALDI was evaluated. Finally, molecular modeling (density functional theory study) of the optimized geometry and stereochemistry of E-cinnamic and Z-cinnamic acids revealed some factors governing the analyte-matrix interaction. Copyright © 2013 John Wiley & Sons, Ltd.
Registro:
| Documento: | Artículo |
| Título: | Z-sinapinic acid: The change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI-MS analysis |
| Autor: | Salum, M.L.; Itovich, L.M.; Erra-Balsells, R. |
| Filiación: | CIHIDECAR-Departamento de Química Orgánica, FCEN, Universidad de Buenos Aires, Pabellõn II, 3er P, 1428 Buenos Aires, Argentina |
| Palabras clave: | E-coumaric acid; E-ferulic acid; E-sinapinic acid; neutral carbohydrates; sulfated carbohydrates; Z-coumaric acid; Z-ferulic acid; Z-sinapinic acid; 3 ,5-dihydroxybenzoic acid; Cinnamic acid derivatives; Crystalline matrices; Cyano-4-hydroxycinnamic acids; Density functional theory studies; Matrix assisted laser desorption/ionization; Morphological properties; Photochemical stability; Chemical bonds; Geometry; Isomers; Stereochemistry; Stereoselectivity; Carbohydrates; anion; cinnamic acid; ferulic acid; para coumaric acid; sinapic acid; carbohydrate; cinnamic acid; cinnamic acid derivative; coumaric acid; sinapic acid; amino acid synthesis; article; carbohydrate analysis; carbon nuclear magnetic resonance; chemical structure; controlled study; dissociation; high performance liquid chromatography; isomer; isomerization; limit of detection; matrix assisted laser desorption ionization time of flight mass spectrometry; molecular interaction; photochemistry; priority journal; proton nuclear magnetic resonance; solid state; stereochemistry; ultraviolet spectroscopy; chemistry; mass spectrometry; procedures; stereoisomerism; Carbohydrates; Cinnamates; Coumaric Acids; Models, Molecular; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Stereoisomerism |
| Año: | 2013 |
| Volumen: | 48 |
| Número: | 11 |
| Página de inicio: | 1160 |
| Página de fin: | 1169 |
| DOI: | http://dx.doi.org/10.1002/jms.3281 |
| Título revista: | Journal of Mass Spectrometry |
| Título revista abreviado: | J. Mass Spectrom. |
| ISSN: | 10765174 |
| CODEN: | JMSPF |
| CAS: | cinnamic acid, 4151-45-5, 538-42-1, 621-82-9; ferulic acid, 1135-24-6, 24276-84-4; para coumaric acid, 7400-08-0; sinapic acid, 530-59-6; coumaric acid, 25429-38-3; Carbohydrates; Cinnamates; cinnamic acid; Coumaric Acids; sinapinic acid |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10765174_v48_n11_p1160_Salum |
Referencias:
- Beavis, R.C., Chait, B.T., Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins (1989) Rapid Commun. Mass Spectrom., 3, p. 432
- Beavis, R.C., Chaudhary, T., Chait, B.T., α-Cyano-4-hydroxycinnamic acid as a matrix for matrix-assisted laser desorption mass spectrometry (1992) Org. Mass Spectrom., 27, p. 156
- Schneider, K., Chait, B.T., Matrix-assisted laser desorption mass spectrometry of homopolymer oligodeoxyribonucleotides. Influence of base composition on the mass spectrometric response (1993) IRapid Commun. Mass Spectrom., 28, p. 1353
- Jaskolla, T.W., Lehmann, W.D., Karas, M., 4-Chloro-α-cyanocinnamic acid is an advanced, rationally designed MALDI matrix (2008) Proc. Natl. Acad. Sci. U. S. A., 105, p. 12200
- Porta, T., Grivet, C., Knochenmuss, R., Varesioa, E., Hopfgartner, G., Alternative CHCA-based matrices for the analysis of low molecular weight compounds by UV-MALDI-tandem mass spectrometry (2011) J. Mass Spectrom., 46, p. 144
- Buchanan, B.B., Gruissem, W., Jones, R.L., (2000) Biochemistry & Molecular Biology of Plants, p. 1286. , American Society of Plant Physiologist, Rockville. Chapter 24
- Salum, M.L., Erra-Balsells, R., High purity cis-cinnamic acid preparation for studying physiological role of trans-cinnamic and cis-cinnamic acids in higher plants (review) (2013) Environ. Control in Biol., 51, p. 1
- Mori, T., Inoue, Y., (2005) C=C Photoinduced Isomerization Reactions, p. 417. , in, A. G. Griesbeck and J. Mattay (Eds). Synthetic Organic Photochemistry, Marcel Dekker: New York
- Arai, T., Organic molecular photochemistry (1999) Photochemical Cis-Trans Isomerization in the Triplet State, p. 131. , in Vol 3, Molecular and Supramolecular Photochemistry, V. Ramamurthy and K. S. Schanze (Eds), CRC press: Boca Raton, Florida, USA
- Rao, V.J., Organic molecular photochemistry (1999) Photochemical Cis-Trans Isomerization from the Singlet State, p. 169. , in Vol 3. Molecular and Supramolecular Photochemistry, V. Ramamurthy, K. S. Schanze (Eds). CRC press: Boca Raton, Florida, USA
- Nieuwendaal, R.C., Bertmer, M., Hayes, S.E., An unexpected phase transition during the [2+2] photocycloaddition reaction of cinnamic acid to truxillic acid: Changes in polymorphism monitored by solid-state NMR (2008) J. Phys. Chem. B, 112, p. 12920
- Feringa, B.L., Van Delden, R.A., Koumura, N., Geertsema, E.M., Chiroptical molecular switches (2000) Chem. Rev., 100, p. 1789
- Klessinger, M., Michl, J., (1995) Excited States and Photochemistry of Organic Molecules, p. 362. , VCH Publishers, Inc.: New York
- Turro, N.J., Ramamurthy, V., Scaiano, J.C., (2009) Principles of Molecular Photochemistry: An Introduction, p. 319. , University Science Books: Sausalito
- Parthasarathy, A., Samanta, S.R., Ramamurthy, V., Photodimerization of hydrophobic guests within a water-soluble nanocapsule (2013) Res. Chem. Interm., 39, p. 73
- Salum, M.L., Robles, C.J., Erra-Balsells, R., Photoisomerization of ionic liquids ammonium cinnamates: One-pot synthesis-isolation of Z-cinnamic acids (2010) Org. Lett., 12, p. 4808
- Salum, M.L., Erra-Balsells, R., (2009) One-pot Synthesis of Z-cinnamic Acids, , Argentine Patent, CONICET #20090105020
- Gholipour, Y., Nonami, H., Erra-Balsells, R., In situ analysis of plant tissue underivatized carbohydrates and on-probe enzymatic degraded starch by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry by using carbon nanotubes as matrix (2008) Anal. Biochem., 383, p. 159
- Gholipour, Y., Giudicessi, S.L., Nonami, H., Erra-Balsells, R., Diamond, titanium dioxide, strontium titanium oxide, and barium strontium titanium oxide nanoparticles for direct matrix assisted laser desorption/ionization mass spectrometry analysis of soluble carbohydrates in plant tissues (2010) Anal. Chem., 82, p. 5518
- Mohr, M.D., Börnsen, O.K., Widmer, H.M., Matrix-assisted laser desorption/ionization mass spectrometry: Improved matrix for oligosaccharides (1995) R. Commun. Mass Spectrom., 9, p. 809
- Dai, Y., Whittal, R.M., Bridges, C.A., Isogai, Y., Hindsgaul, O., Li, L., Matrix-assisted laser desorption ionization mass spectrometry for the analysis of monosulfated oligosaccharides (1997) Carbohydr. Res., 304, p. 1
- Harvey, D.J., Matrix-assisted laser desorption/ionization mass spectrometry of carbohydrates (1999) Mass Spectrom. Rev., 18, p. 349
- Harvey, D.J., Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: An update covering the period 2007-2008 (2012) Mass Spectrom. Rev., 31, p. 183
- Fukuyama, Y., Nakaya, S., Yamazaki, Y., Tanaka, K., Ionic liquid matrixes optimized for MALDI-MS of sulfated/sialylated/ neutral oligosaccharides and glycopeptides (2008) Anal. Chem., 80, p. 2171
- Fukuyama, Y., Ciancia, M., Erra-Balsells, R., Matulewicz, M.C., Nonami, H., Cerezo, A.S., Matrix-assisted ultraviolet laser desorption ionization time-of-flight mass spectrometry of sulfated carrageenan oligosaccharides (2002) Carbohydr. Res., 337, p. 1553
- Li, L., Golding, R.E., Whittal, R.M., Analysis of single mammalian cell lysates by mass spectrometry (1996) J. Am. Chem. Soc., 118, p. 11662
- Salum, M.L., Erra-Balsells, R., Effect of Water and Aliphatic Amines on the UV-absorption Spectra of E- And Z-cinnamic Acids in Methanol Solution (Paper Is under Preparation)
- Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Pople, J.A., (1998) Gaussian 98W, , Revision A.3., Gaussian 98, Revision A.3, Gaussian, Inc., Pittsburgh PA
- (2010) HyperChem 8.08 for Windows, , HyperCube Inc.: Ontario
- Ehring, H., Sundqvist, B.U.R., Studies of the MALDI process by luminescence spectroscopy (1995) J. Mass Spectrom., 30, p. 1303
- Ehring, H., Sundqvist, B.U.R., Excited-state relaxation processes of MALDI-matrices studied by luminescence spectroscopy (1996) Appl. Surf. Sci., 577, p. 96
- Alllwood, D.A., Dyer, P.E., Quantitative fluorescence measurements performed on typical matrix molecules in matrix-assisted laser desorption/ionization (2000) Chem. Phys., 261, p. 457
- Lüdemann, H.-C., Redmond, R.W., Hillenkamp, F., Singlet-singlet annihilation in ultraviolet matrix-assisted laser desorption/ionization studied by fluorescence spectroscopy (2002) R. Comunn. Mass Spectrom., 116, p. 1287
Citas:
---------- APA ----------
Salum, M.L., Itovich, L.M. & Erra-Balsells, R. (2013) . Z-sinapinic acid: The change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI-MS analysis. Journal of Mass Spectrometry, 48(11), 1160-1169.http://dx.doi.org/10.1002/jms.3281
---------- CHICAGO ----------
Salum, M.L., Itovich, L.M., Erra-Balsells, R. "Z-sinapinic acid: The change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI-MS analysis" . Journal of Mass Spectrometry 48, no. 11 (2013) : 1160-1169.http://dx.doi.org/10.1002/jms.3281
---------- MLA ----------
Salum, M.L., Itovich, L.M., Erra-Balsells, R. "Z-sinapinic acid: The change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI-MS analysis" . Journal of Mass Spectrometry, vol. 48, no. 11, 2013, pp. 1160-1169.http://dx.doi.org/10.1002/jms.3281
---------- VANCOUVER ----------
Salum, M.L., Itovich, L.M., Erra-Balsells, R. Z-sinapinic acid: The change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI-MS analysis. J. Mass Spectrom. 2013;48(11):1160-1169.http://dx.doi.org/10.1002/jms.3281
