The laser desorption (LD) ionization of three stilbenes in the nano porous metal–organic frameworks called “crystalline sponge” is demonstrated. The analyte position in the pore and the interaction between the analyte and the framework that functions as a matrix are discussed based on the results of single-crystal X-ray analysis. It is confirmed that the analyte/ligand ratio of 1: 2 is sufficient for the analyte ionization. This method makes it possible to visualize hot spots on a target plate to be irradiated. That the sample requirement is dramatically reduced to the order of femtomoles is also an advantage. The relationship between laser interaction, analyte position in the pore, and analyte/ligand ratio is discussed as a new ionization field to elucidate the molecular structure of the analyte by LD ionization mass spectrometry.
YangX.WuH.KobayashiT.SolaroR. J.van BreemenR.B., “Enhanced ionization of phosphorylated peptides during MALDI-TOF mass spectrometry”, Anal. Chem.76, 1532 (2004). doi: http://dx.doi.org/10.1021/ac035203v
2.
KjellströmS.JensenO.N., “Phosphoric acid as a matrix additive for MALDI MS analysis of phosphopeptides and phosphoproteins”, Anal. Chem.76, 5109 (2004). doi: http://dx.doi.org/10.1021/ac0400257
3.
UekiM.YamaguchiM., “Enhanced detection of sulfo-peptides as onium salts in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry”, Rapid Commun. Mass Spectrom.20, 1615 (2006). doi: http://dx.doi.org/10.1002/rcm.2480
4.
NishikazeT.TakayamaM., “Disappearance of interfering alkali-metal adducted peaks from matrix-assisted laser desorption/ionization mass spectra of peptides with serine addition to α-cyano-4-hydroxycinnamic acid matrix”, Rapid Commun. Mass Spectrom.21, 3345 (2007). doi: http://dx.doi.org/10.1002/rcm.3219
5.
KangJ.-H.ToitaR.OishiJ.NiidomeT.KatayamaY., “Effect of the addition of diammonium citrate to α-cyano-4-hydroxycinnamic acid (CHCA) matrix for the detection of phosphorylated peptide in phosphorylation reactions using cell and tissue lysates”, J. Am. Soc. Mass Spectrom.18, 1925 (2007). doi: http://dx.doi.org/10.1016/j.jasms.2007.08.002
6.
KuyamaH.SonomuraK.NishimuraO., “Sensitive detection of phosphopeptides by matrix-assisted laser desorption/ionization mass spectrometry: Use of alkylphosphonic acids as matrix additives”, Rapid Commun. Mass Spectrom.22, 1109 (2008), doi: http://dx.doi.org/10.1002/rcm.3482
7.
FukuyamaY.TakeyamaK.KawabataS.IwamotoS.TanakaK., “An optimized matrix-assisted laser desorption/ionization sample preparation using a liquid matrix, 3-aminoquinoline/α-cyano-4-hydroxycinnamic acid, for phosphopeptides”, Rapid Commun. Mass Spectrom.26, 2454 (2012). doi: http://dx.doi.org/10.1002/rcm.6363
8.
BashirS.MutterR.DerrickP.J., “Parameterising matrix-assisted laser desorption / ionization (MALDI): Effect of solvents and co-additives on analyte peak intensities”, Eur. J. Mass Spectrom.10, 487 (2004). doi: http://dx.doi.org/10.1255/ejms.645
9.
YamaguchiS.FujitaT.FujinoT.KorenagaT., “Suppression of matrix-related ions using cyclodextrin in MALDI mass spectrometry”, Anal. Sci.24, 1497 (2008). doi: http://dx.doi.org/10.2116/analsci.24.1497
10.
FujitaT.FujinoT.HirabayashiK.KorenagaT., “MALDI mass spectrometry using 2,4,6-trihydroxyacetophenone and 2,4-dihydroxyacetophenone with cyclodextrins: Suppression of matrix-related ions in low-molecular-weight region”, Anal. Sci.26, 743 (2010). doi: http://dx.doi.org/10.2116/analsci.26.743
11.
KomoriY.ShimaH.FujinoT.KondoJ.N.HashimotoK.KorenagaT., “Pronounced selectivity in matrix-assisted laser desorption – ionization mass spectrometry with 2,4,6-trihydroxyacetophenone on a zeolite surface: Intensity enhancement of protonated peptides and suppression of matrix-related ions”, J. Phys. Chem. C114, 1593 (2010). doi: http://dx.doi.org/10.1021/jp907892y
12.
SuzukiJ.FujinoT., “Matrix-assisted laser desorption ionization mass spectrometry of maltohexaose and acetylsalicylic acid using alkali metal cation-substituted zeolites”, Anal. Sci.28, 901 (2012). doi: http://dx.doi.org/10.2116/analsci.28.901
13.
PanC.YeM.LiuY.FengS.JiangX.HanG.ZhuJ.ZouH., “Enrichment of phosphopeptides by Fe3+–immobilized mesoporous nanoparticles of MCM-41 for MALDI and nano-LC-MS/MS analysis”, J. Proteome. Res.5, 3114 (2006). doi: http://dx.doi.org/10.1021/pr0600125
14.
FujinoT.SuzukiJ.YamamotoR., “Cation-selective ionization of biologically active substances using zeolites”, Sci. Adv. Mater.6, 1590 (2014). doi: http://dx.doi.org/10.1166/sam.2014.1798
15.
AsanoT.SuzukiJ.HashimotoK.FujinoT., “Laser desorption ionization mass spectrometry of bioactive substances by using 2,4,6-trihydroxyacetophenone of cation-substituted zeolite”, Anal. Sci.29, 1035 (2013). doi: http://dx.doi.org/10.2116/analsci.29.1035
16.
WangF.GuanY.ZhangS.XiaY., “Hydrophilic modification of silica-titania mesoporous materials as restricted-access matrix adsorbents for enrichment of phosphopeptides”J. Chromatogr. A1246, 76 (2012). doi: http://dx.doi.org/10.1016/j.chroma.2012.02.050
17.
ArakawaR.KawasakiH., “Functionalized nanoparticles and nanostructured surfaces for surface-assisted laser desorption/ionization mass spectrometry”, Anal. Sci.26, 1229 (2010). doi: http://dx.doi.org/10.2116/analsci.26.1229
18.
ZhangY.YuX.WangX.ShanW.YangP.TangY., “Zeolite nanoparticles with immobilized metal ions: Isolation and MALDI-TOF-MS/MS identification of phosphopeptides”, Chem. Commun.2882 (2004). doi: http://dx.doi.org/10.1039/B411336E
PiretG.DrobecqH.CoffinierY.MelnykO.BoukherroubR., “Matrix-free laser desorption/ionization mass spectrometry on silicon nanowire arrays prepared by chemical etching of crystalline silicon”, Langmuir26, 1354 (2010). doi: http://dx.doi.org/10.1021/la902266x
21.
GuéninE.LecouveyM.HardouinJ., “Could a nanoassisted laser desorption/ionization target improve the study of small organic molecules by laser desorption/ionization time-of-flight mass spectrometry?”, Rapid Commun. Mass Spectrom.23, 1395 (2009). doi: http://dx.doi.org/10.1002/rcm.4002
22.
TsaoC.-W.KumarP.LiuJ.DeVoeD.L., “Dynamic electrowetting on nanofilament silicon for matrix-free laser desorption/ionization mass spectrometry”, Anal. Chem.80, 2973 (2008). doi: http://dx.doi.org/10.1021/ac7026029
23.
LoweR.D.SziliE.J.KirkbrideP.ThissenH.SiuzdakG.VoelckerN.H., “Combined immunocapture and laser desorption/ionization mass spectrometry on porous silicon”, Anal. Chem.82, 4201 (2010). doi: http://dx.doi.org/10.1021/ac100455x
24.
HuL.XuS.PanC.ZouH.JiangG., “Preparation of a biochip on porous silicon and application for label-free detection of small molecule-protein interactions”, Rapid Commun. Mass Spectrom.21, 1277 (2007). doi: http://dx.doi.org/10.1002/rcm.2944
25.
ShenarN.CantelS.MartinezJ.EnjalbalC., “Comparison of inert supports in laser desorption/ionization mass spectrometry of peptides: Pencil lead, porous silica gel, DIOS-chip and NALDI™ target”Rapid Commun. Mass Spectrom.23, 2371 (2009). doi: http://dx.doi.org/10.1002/rcm.4158
26.
MandalS.M.DeD.RoyS.K.GhoshA.K.RamS.DasA.K., “Lanthanum-calcium-manganate (La0.67Ca0.33MnO3) nanoparticle assisted affinity probes for MALDI MS analysis of proteins”, Eur. J. Mass Spectrom.13, 359 (2007). doi: http://dx.doi.org/10.1255/ejms.893
InokumaY.YoshiokaS.AriyoshiJ.AraiT.HitoraY.TakadaK.MatsunagaS.RissanenK.FujitaM., “X-ray analysis on the nanogram to microgram scale using porous complexes”, Nature495, 461 (2013). doi: http://dx.doi.org/10.1038/nature11990
29.
OharaK.InokumaY.FujitaM., “The catalytic Z to E isomerization of stilbenes in a photosensitizing porous coordination network”, Angew. Chem. Int. Ed.49, 5507 (2010). doi: http://dx.doi.org/10.1002/anie.201001902
30.
OharaK.KawanoM.InokumaY.FujitaM., “A porous coordination network catalyzes an olefin isomerization reaction in the pore”J. Am. Chem. Soc.132, 30 (2010). doi: http://dx.doi.org/10.1021/ja908794n
31.
VinogradovaE.V.MüllerP.BuchwaldS.L., “Structural reevaluation of the electrophilic hypervalent iodine reagent for trifluoromethylthiolation supported by the crystalline sponge method for X-ray analysis”, Angew. Chem. Int. Ed.53, 3125 (2014). doi: http://dx.doi.org/10.1002/anie.201310897
32.
HolleA.HaaseA.KayserM.HöhndortJ., “Optimizing UV laser focus profiles for improved MALDI performance”, J. Mass Spectrom.41, 705 (2006). doi: http://dx.doi.org/10.1002/jms.1041
33.
MalloryF.B.WoodC.S.GordonJ.T., “Photochemistry of stilbenes. III. Some aspects of the mechanism of photocyclization to phenanthrenes”, J. Am. Chem. Soc.86, 3094 (1964). doi: http://dx.doi.org/10.1021/ja01069a025
34.
HillenkampF.KarasM.BeavisR.C.ChaitB.T., “Matrix-assisted desorption/ionization mass spectrometry of biopolymers”, Anal. Chem.63, 1193A (1991). doi: http://dx.doi.org/10.1021/ac00024a716
