CA2697151A1 - Use of cyanocinnamic acid derivatives as matrices in maldi mass spectrometry - Google Patents
Use of cyanocinnamic acid derivatives as matrices in maldi mass spectrometry Download PDFInfo
- Publication number
- CA2697151A1 CA2697151A1 CA2697151A CA2697151A CA2697151A1 CA 2697151 A1 CA2697151 A1 CA 2697151A1 CA 2697151 A CA2697151 A CA 2697151A CA 2697151 A CA2697151 A CA 2697151A CA 2697151 A1 CA2697151 A1 CA 2697151A1
- Authority
- CA
- Canada
- Prior art keywords
- matrix
- cyanocinnamic acid
- acid
- mass spectrometry
- cyanocinnamic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000004949 mass spectrometry Methods 0.000 title claims abstract description 22
- CDUQMGQIHYISOP-UHFFFAOYSA-N 2-cyano-3-phenylprop-2-enoic acid Chemical class OC(=O)C(C#N)=CC1=CC=CC=C1 CDUQMGQIHYISOP-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 239000012491 analyte Substances 0.000 claims abstract description 27
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 claims abstract 6
- 239000011159 matrix material Substances 0.000 claims description 61
- 150000002500 ions Chemical class 0.000 claims description 33
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 19
- AFVLVVWMAFSXCK-VMPITWQZSA-N alpha-cyano-4-hydroxycinnamic acid Chemical group OC(=O)C(\C#N)=C\C1=CC=C(O)C=C1 AFVLVVWMAFSXCK-VMPITWQZSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 108090000623 proteins and genes Proteins 0.000 claims description 8
- 102000004169 proteins and genes Human genes 0.000 claims description 8
- CUIZHZDTLJKDBH-UHFFFAOYSA-N 3-(4-chloro-2-cyanophenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=C(Cl)C=C1C#N CUIZHZDTLJKDBH-UHFFFAOYSA-N 0.000 claims description 7
- PCMORTLOPMLEFB-ONEGZZNKSA-N sinapic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-ONEGZZNKSA-N 0.000 claims description 7
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims description 6
- VSMAAVBAABUVMQ-UHFFFAOYSA-N 2-cyano-3-(4-methylphenyl)prop-2-enoic acid Chemical compound CC1=CC=C(C=C(C#N)C(O)=O)C=C1 VSMAAVBAABUVMQ-UHFFFAOYSA-N 0.000 claims description 6
- JNXMESYLJCEGFE-UHFFFAOYSA-N 3-(6-cyano-4,6-difluorocyclohexa-2,4-dien-1-yl)prop-2-enoic acid Chemical group FC1(C(C=CC(=O)O)C=CC(=C1)F)C#N JNXMESYLJCEGFE-UHFFFAOYSA-N 0.000 claims description 6
- PCMORTLOPMLEFB-UHFFFAOYSA-N sinapinic acid Natural products COC1=CC(C=CC(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-UHFFFAOYSA-N 0.000 claims description 5
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 claims description 2
- 235000001785 ferulic acid Nutrition 0.000 claims description 2
- 229940114124 ferulic acid Drugs 0.000 claims description 2
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 235000018102 proteins Nutrition 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 235000001014 amino acid Nutrition 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000029087 digestion Effects 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 241000894007 species Species 0.000 description 3
- BRARRAHGNDUELT-UHFFFAOYSA-N 3-hydroxypicolinic acid Chemical compound OC(=O)C1=NC=CC=C1O BRARRAHGNDUELT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003275 alpha amino acid group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002288 cocrystallisation Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 238000001906 matrix-assisted laser desorption--ionisation mass spectrometry Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000013777 protein digestion Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NPWMTBZSRRLQNJ-VKHMYHEASA-N (3s)-3-aminopiperidine-2,6-dione Chemical compound N[C@H]1CCC(=O)NC1=O NPWMTBZSRRLQNJ-VKHMYHEASA-N 0.000 description 1
- CDUQMGQIHYISOP-RMKNXTFCSA-N (e)-2-cyano-3-phenylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C\C1=CC=CC=C1 CDUQMGQIHYISOP-RMKNXTFCSA-N 0.000 description 1
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940008126 aerosol Drugs 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 210000004900 c-terminal fragment Anatomy 0.000 description 1
- 238000007623 carbamidomethylation reaction Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 238000004989 laser desorption mass spectroscopy Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000001869 matrix assisted laser desorption--ionisation mass spectrum Methods 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 108091033319 polynucleotide Proteins 0.000 description 1
- 102000040430 polynucleotide Human genes 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6848—Methods of protein analysis involving mass spectrometry
- G01N33/6851—Methods of protein analysis involving laser desorption ionisation mass spectrometry
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/24—Nuclear magnetic resonance, electron spin resonance or other spin effects or mass spectrometry
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Bioinformatics & Computational Biology (AREA)
- Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Microbiology (AREA)
- Medicinal Chemistry (AREA)
- Biotechnology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Optics & Photonics (AREA)
- Food Science & Technology (AREA)
- Cell Biology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007040251.3 | 2007-08-27 | ||
| DE102007040251A DE102007040251B3 (de) | 2007-08-27 | 2007-08-27 | Verwendung von Cyanozimtsäurederivaten als Matrizes in MALDI-Massenspektrometrie |
| PCT/DE2008/001149 WO2009026867A1 (de) | 2007-08-27 | 2008-07-10 | Verwendung von cyanozimtsäurederivaten als matrizes in maldi-massenspektrometrie |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2697151A1 true CA2697151A1 (en) | 2009-03-05 |
Family
ID=39942809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2697151A Abandoned CA2697151A1 (en) | 2007-08-27 | 2008-07-10 | Use of cyanocinnamic acid derivatives as matrices in maldi mass spectrometry |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8980642B2 (enExample) |
| EP (1) | EP2183600B1 (enExample) |
| JP (1) | JP5529020B2 (enExample) |
| CA (1) | CA2697151A1 (enExample) |
| DE (1) | DE102007040251B3 (enExample) |
| WO (1) | WO2009026867A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102010010155A1 (de) | 2010-03-04 | 2011-09-08 | Johann Wolfgang Goethe-Universität | Verwendung von halogenierten Cyanozimtsäurederivaten als Matrizes in MALDI-Massenspektrometrie |
| JP6083595B2 (ja) * | 2011-11-21 | 2017-02-22 | 公立大学法人横浜市立大学 | タンパク質とリン酸化ペプチドのペプチド主鎖のＮ−Ｃα結合又はＣα−Ｃ結合の特異的切断方法 |
| JP5980517B2 (ja) * | 2012-02-13 | 2016-08-31 | 株式会社島津製作所 | 質量分析用マトリックスの添加剤 |
| NL2022038B1 (en) | 2018-11-21 | 2020-06-05 | Biosparq B V | Method for analysing an analyte sample and matrix material therefore |
| CN116917726A (zh) * | 2021-02-10 | 2023-10-20 | 株式会社岛津制作所 | 有机合成化合物的质谱分析法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020142982A1 (en) * | 1999-09-02 | 2002-10-03 | Timothy Hla | Method for regulating angiogenesis |
| DE10158860B4 (de) * | 2001-11-30 | 2007-04-05 | Bruker Daltonik Gmbh | Massenspektrometrische Proteingemischanalyse |
| JP4606028B2 (ja) * | 2002-04-04 | 2011-01-05 | エレクトロフォレティクス リミテッド | 被分析物の分析方法 |
| DE10322701B4 (de) * | 2003-05-20 | 2006-12-28 | Humboldt-Universität Zu Berlin | Probenträger unter Verwendung eines porösen, Metalloxidpartikel umfassenden Films, Verfahren zur Herstellung eines Probenträgers, Verwendung des Probenträgers sowie Verfahren zum selektiven Nachweis von phosphorylierten/sulfatierten Biopolymeren, insbesondere Peptiden/Proteinen |
| JP4165501B2 (ja) * | 2004-04-13 | 2008-10-15 | 株式会社島津製作所 | Ｍａｌｄｉ質量分析装置による疎水性ペプチドの測定方法 |
| US20060261267A1 (en) * | 2005-05-20 | 2006-11-23 | Agency For Science, Technology And Research | Composite MALDI matrix material and methods of using it and kits thereof in MALDI |
-
2007
- 2007-08-27 DE DE102007040251A patent/DE102007040251B3/de not_active Expired - Fee Related
-
2008
- 2008-07-10 EP EP08784332.2A patent/EP2183600B1/de not_active Not-in-force
- 2008-07-10 WO PCT/DE2008/001149 patent/WO2009026867A1/de not_active Ceased
- 2008-07-10 CA CA2697151A patent/CA2697151A1/en not_active Abandoned
- 2008-07-10 US US12/675,569 patent/US8980642B2/en not_active Expired - Fee Related
- 2008-07-10 JP JP2010522176A patent/JP5529020B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP5529020B2 (ja) | 2014-06-25 |
| JP2010537206A (ja) | 2010-12-02 |
| EP2183600A1 (de) | 2010-05-12 |
| US20110121166A1 (en) | 2011-05-26 |
| DE102007040251B3 (de) | 2009-01-08 |
| WO2009026867A1 (de) | 2009-03-05 |
| US8980642B2 (en) | 2015-03-17 |
| EP2183600B1 (de) | 2014-09-03 |
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| EEER | Examination request |
Effective date: 20130530 |
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| FZDE | Discontinued |
Effective date: 20170711 |