Negative Ion Ultraviolet Matrix-Assisted Laser Desorption Ionization Mass Spectrometry and Post Source Decay of Glycosyl Esters of Nucleoside Pyrophosphates
Restricted accessResearch articleFirst published online December, 2008
Negative Ion Ultraviolet Matrix-Assisted Laser Desorption Ionization Mass Spectrometry and Post Source Decay of Glycosyl Esters of Nucleoside Pyrophosphates
Six different glycosyl esters of nucleoside pyrophosphates (monosaccharide nucleotides) were analyzed by means of matrix-assisted laser desorption/ionisation reflectron time-of-flight mass spectrometry (MALDI/RToF MS) in the negative ion mode. Several matrices were evaluated and 3-hydroxypicolinic acid as well as α-cyano-4-hydroxycinnamic acid (CHCA) turned out to be the matrices of choice applying the thin layer technique to obtain maximum sensitivity for deprotonated molecular ion detection and maximal fragmentation particular with CHCA. The determination of the molecular mass with a mass accuracy below 0.1% was feasible with sample amounts in the lower femtomole range applying a MALDI desk-top mass spectrometer. A further important refinement of this technique was the use of post source decay (PSD) fragment ion analysis with a curved field reflector (which means no stepping of the reflector voltage). Detailed structural information of the six selected monosaccharide nucleotides could be obtained with PSD and differences in the fragmentation pattern were used to distinguish them. This method (based on molecular mass and PSD fragment ion analysis) has been applied to verify the presence of a glycosyl ester of nucleoside pyrophosphate in samples from Saccharomyces cerevisiae.
HartmannE.MessnerP.AllmaierG.KönigH., “Proposed pathway for biosynthesis of the S-layer glycoprotein of Bacillus alvei”, J. Bacteriol.175, 4515 (1993).
5.
SprengerS.KönigH., “Evidence for the occurrence of nucleotide-activated oligosaccharides in Saccharomyces cerevisiae”, Can. J. Microbiol.46, 490 (2000). doi: 10.1139/cjm-46-5-490
6.
FukusakiE.KobayashiA., “Plant metabolomics: Potential for practical operations”, J. Biosci. Bioeng.100, 347 (2005). doi: 10.1263/jbb.100.347
7.
SchneiderP.McConvilleM.J.FergusonM.A.J., “Characterization of GDP-α-D-arabinopyranose, the precursor of D-Arap in Leishmania major lipophosphoglycan”, J. Biol. Chem.269, 18332 (1994).
8.
SchrammK.H., “Analysis of nucleosides, nucleotides and oligonucleotides using fast atom bombardment mass spectrometry”, Trends Anal. Chem.7, 28 (1988). doi: 10.1016/0165-9936(88)80027-X
9.
WoluckaB.A.de HoffmanE., “Determination of the anomeric configuration of glycosyl esters of nucleoside pyrophosphates by fast atom bombardment tandem mass spectrometry”, J. Am. Soc. Mass Spectrom.6, 516 (1995). doi: 10.1016/1044-0305(95)00030-H
10.
WoluckaB.A.de HoffmanE.RushJ.S.WaechterC.J., “Determination of the anomeric configuration of glycosyl esters of nucleoside pyrophosphates and polyisoprenyl phosphates by fast atom bombardment tandem mass spectrometry”, J. Am. Soc. Mass Spectrom.7, 541 (1996). doi: 10.1016/1044-0305(96)00020-7
11.
LiguoriA.MaiuoloL.NinoA.D.ProcopioA.SindonaG., “The structure characterization of dinucleoside and nucleoside glucopyranosides lipophilic phosphotriesters by fast atom bombardment tandem mass spectrometry”, J. Am. Soc. Mass Spectrom.10, 975 (1999). doi: 10.1016/S1044-0305(99)00066-5
12.
NordhoffE., “MALDI mass spectrometry as a new method for the characterization of nucleic acids”, Trends Anal. Chem.15, 240 (1996). doi: 10.1016/0165-9936(96)00020-9
13.
ChiuN.H.L.CantorC.R., “Mass spectrometry of nucleic acids”, Clin. Chem.45, 1578 (1999).
14.
ComptonB.J.SiuzdakG., “Mass spectrometry in nucleic acid, carbohydrate and steroid analysis”, Spectroscopy17, 699 (2003).
15.
WoluckaB.A.RushJ.S.WaechterC.J.ShibaevV.N.de HoffmannE., “An electrospray ionization tandem mass spectrometry method for determination of the anomeric configuration of glycosyl 1-phosphate derivatives”, Anal. Biochem.255, 244 (1998). doi: 10.1006/abio.1997.2421
16.
KaufmannR.KirschD.SpenglerB., “Sequencing of peptides in a time-of-flight MS: Evaluation of postsource decay following matrix-assisted laser desorption ionization (MALDI)”, Int J. Mass Spectrom. Ion Processes131, 355 (1994). doi: 10.1016/0168-1176(93)03876-N
17.
HankinJ.A.MurphyR.C., “MALDI-TOF and ESI tandem mass spectrometric analysis of fatty acyl-CoA esters”, Int. J. Mass Spectrom. Ion Processes165/166, 467 (1997). doi: 10.1016/S0168-1176(97)00172-9
18.
JankowskiJ.Große-HüttmannP.ZidekW.SchlüterH., “Identification of dinucleoside polyphosphates by MALDI post source decay mass spectrometry”, Rapid Commun. Mass Spectrom.17, 1189 (2003). doi: 10.1002/rcm.1035
19.
CorderoM.M.CornishT.J.CotterR.J.LysI.A., “Sequencing peptides without scanning the reflectron: Post-source decay with a curved-field reflectron time-of-flight mass spectrometer”, Rapid Commun. Mass Spectrom.9, 1356 (1995). doi: 10.1002/rcm.1290091407
20.
CornishT.J.CotterR.J., “A curved-field reflectron for improved energy focusing of product ions in time-of-flight mass spectrometry”, Rapid Commun. Mass Spectrom.7, 1037 (1993). doi: 10.1002/rcm.1290071114
21.
WoodsA.S.LittleD.P.CornishT.J.CotterR.J., “Peptide analysis to the attomole level using a curved-field reflectron MALDI-TOF mass spectrometer”, J. Mass Spectrom. Soc. Japan46, 91 (1998).
22.
CotterR.J.GriffithW.JelinekC., “Tandem time-of-flight (ToF/ToF) mass spectrometry and the curved-field reflectron”, J. Chromatogr. B855, 2 (2007). doi: 10.1016/j.jchromb.2007.01.009
23.
VormO.RoepstorffP.MannM., “Improved resolution and very high sensitivity in MALDI TOF of matrix surfaces made by fast evaporation”, Anal. Chem.66, 3281 (1994). doi: 10.1021/ac00091a044
24.
StrupatK.KarasM.HillenkampF., “2,5-Dihydroxybenzoic acid: A new matrix for laser desorption-ionization mass spectrometry”, Int. J. Mass Spectrom. Ion Processes111, 89 (1991). doi: 10.1016/0168-1176(91)85050-V
25.
SprengerS., PhD thesis, University of Ulm, Ulm, Germany (1996).
26.
HarveyD.J., “Matrix-assisted laser desorption/ionisation mass spectrometry of oligosaccharides and glycoconjugates”, J. Chromatogr.720, 429 (1996). doi: 10.1016/0021-9673(95)00307-X
27.
WuK.J.StedingA.BeckerC.H., “Matrix-assisted laser desorption time-of-flight mass spectrometry of oligonucleotides using 3-hydroxypicolinic acid as an ultraviolet-sensitive matrix”, Rapid. Commun. Mass Spectrom.7, 142 (1993). doi: 10.1002/rcm.1290070206
28.
NordhoffE.KarasM.HahnerS.HillenkampF.KirpekarF.LeziusA.MuthJ.MeierC.EngelsJ.W., “Direct mass spectrometric sequencing of low-picomole amounts of oligodeoxynucleotides with up to 21 bases by matrix-assisted laser desorption/ionization mass spectrometry”, J. Mass Spectrom.30, 99(1995). doi: 10.1002/jms.1190300116
29.
LiuY.BaiJ.LiangX.LubmanD.M.VentaP.J., “Use of a nitrocellulose film substrate in matrix-assisted laser desorption/ionization mass spectrometry for DNA mapping and screening”, Anal. Chem.67, 3482 (1995). doi: 10.1021/ac00115a017
30.
WuK.J.ShalerT.A.BeckerC.H., “Time-of-flight mass spectrometry of underivatized single-stranded DNA oligomers by matrix-assisted laser desorption”, Anal. Chem.66, 1637 (1994). doi: 10.1021/ac00082a007
31.
BeavisR.C.ChaudharyT.ChaitB.T., “α-Cyano-4-hydroxycinnamic acid, as a matrix for MALDI MS”, Org. Mass Spectrom.27, 156 (1992). doi: 10.1002/oms.1210270217
32.
StimsonE.TruongO.RichterW.J.WaterfieldM.D.BurlingameA.L., “Enhancement of charge remote fragmentation in protonated peptides by high-energy CID MALDI-TOF-MS using “cold” matrixes”, Int. J. Mass Spectrom. Ion Processes169/170, 231 (1997). doi: 10.1016/S0168-1176(97)00227-9
33.
JonesR.B.AllmanS.L.TangK.GarrettW.R.ChenC.H., “Neutralization of negatively charged oligonucleotides”, J. Chem. Phys. Lett.212, 451 (1993). doi: 10.1016/0009-2614(93)87227-T
34.
HathawayG.M., “Characterization of modified and normal deoxyoligonucleotides by MALDI time-of-flight mass spectrometry”, BioTechniques17, 150 (1994).
35.
TangW.NelsonC.M.ZhuL.SmithL.M., “Positive ion formation in the UV MALDI analysis of oligonucleotides by using 2,5-dihdroxybenzoic acid”, J. Am. Soc. Mass Spectrom.8, 218 (1997). doi: 10.1016/S1044-0305(96)00237-1
36.
TangK.AllmanS.L.ChenC.H., “MALDI of oligonucleotides with various matrices”, Rapid Commun. Mass Spectrom.7, 943 (1993). doi: 10.1002/rcm.1290071016
