WO2006080210A1 - Réactif, procédé et ensemble pour améliorer l'efficacité d'ionisation et leur utilisation - Google Patents
Réactif, procédé et ensemble pour améliorer l'efficacité d'ionisation et leur utilisation Download PDFInfo
- Publication number
- WO2006080210A1 WO2006080210A1 PCT/JP2006/300554 JP2006300554W WO2006080210A1 WO 2006080210 A1 WO2006080210 A1 WO 2006080210A1 JP 2006300554 W JP2006300554 W JP 2006300554W WO 2006080210 A1 WO2006080210 A1 WO 2006080210A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- metal complex
- protein
- metal
- kit
- ligand
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 40
- 239000003153 chemical reaction reagent Substances 0.000 title description 14
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 103
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 103
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 84
- 239000003446 ligand Substances 0.000 claims abstract description 36
- 230000035945 sensitivity Effects 0.000 claims abstract description 9
- 235000018102 proteins Nutrition 0.000 claims description 92
- 238000004949 mass spectrometry Methods 0.000 claims description 29
- 229910052697 platinum Inorganic materials 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- 229910052802 copper Inorganic materials 0.000 claims description 19
- 150000002500 ions Chemical class 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 17
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical group N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 claims description 13
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- 229910052737 gold Inorganic materials 0.000 claims description 10
- 229910052804 chromium Inorganic materials 0.000 claims description 9
- 229910052742 iron Inorganic materials 0.000 claims description 9
- 229910052759 nickel Inorganic materials 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 9
- 229910052703 rhodium Inorganic materials 0.000 claims description 9
- 229910052707 ruthenium Inorganic materials 0.000 claims description 9
- 229910052709 silver Inorganic materials 0.000 claims description 9
- 230000007704 transition Effects 0.000 claims description 9
- 125000003275 alpha amino acid group Chemical group 0.000 claims description 7
- 229910052762 osmium Inorganic materials 0.000 claims description 7
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims description 6
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 6
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 claims description 6
- 229910052741 iridium Inorganic materials 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 description 30
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 17
- 230000004048 modification Effects 0.000 description 9
- 238000012986 modification Methods 0.000 description 9
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 239000010931 gold Substances 0.000 description 7
- 239000004475 Arginine Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- -1 triazacycloalkane Chemical compound 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- 238000004807 desolvation Methods 0.000 description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 238000000752 ionisation method Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FWCWJPJYNOBMCC-UHFFFAOYSA-N 3,4-bis(2-aminoethyl)heptane-1,3,4,7-tetramine Chemical compound NCCCC(N)(CCN)C(N)(CCN)CCN FWCWJPJYNOBMCC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002262 Schiff base Substances 0.000 description 3
- 150000004753 Schiff bases Chemical class 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001409 amidines Chemical class 0.000 description 3
- 125000000539 amino acid group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 235000018417 cysteine Nutrition 0.000 description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000009145 protein modification Effects 0.000 description 3
- 239000012460 protein solution Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
- 108091034117 Oligonucleotide Proteins 0.000 description 2
- HSCJRCZFDFQWRP-ABVWGUQPSA-N UDP-alpha-D-galactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(NC(=O)C=C2)=O)O1 HSCJRCZFDFQWRP-ABVWGUQPSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001768 cations Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000004853 protein function Effects 0.000 description 2
- 230000006916 protein interaction Effects 0.000 description 2
- 238000006557 surface reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DRGAZIDRYFYHIJ-UHFFFAOYSA-N 2,2':6',2''-terpyridine Chemical compound N1=CC=CC=C1C1=CC=CC(C=2N=CC=CC=2)=N1 DRGAZIDRYFYHIJ-UHFFFAOYSA-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
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 102000003839 Human Proteins Human genes 0.000 description 1
- 108090000144 Human Proteins Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- 102000004357 Transferases Human genes 0.000 description 1
- 108090000992 Transferases Proteins 0.000 description 1
- HSCJRCZFDFQWRP-UHFFFAOYSA-N Uridindiphosphoglukose Natural products OC1C(O)C(O)C(CO)OC1OP(O)(=O)OP(O)(=O)OCC1C(O)C(O)C(N2C(NC(=O)C=C2)=O)O1 HSCJRCZFDFQWRP-UHFFFAOYSA-N 0.000 description 1
- PYLQLSJFDQLUAF-UHFFFAOYSA-I [Pt+2].[Cr](=O)(=O)([O-])[O-].[Cr](=O)(=O)(O)O.[Cr](=O)(=O)(O)O.[Cr](=O)(=O)([O-])O.[K+] Chemical compound [Pt+2].[Cr](=O)(=O)([O-])[O-].[Cr](=O)(=O)(O)O.[Cr](=O)(=O)(O)O.[Cr](=O)(=O)([O-])O.[K+] PYLQLSJFDQLUAF-UHFFFAOYSA-I 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000965 cold-spray ionisation mass spectrometry Methods 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000012482 interaction analysis Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 102000035118 modified proteins Human genes 0.000 description 1
- 108091005573 modified proteins Proteins 0.000 description 1
- 238000000329 molecular dynamics simulation Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003506 protein modification method Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229940096017 silver fluoride Drugs 0.000 description 1
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000010938 white gold Substances 0.000 description 1
- 229910000832 white gold Inorganic materials 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage
Definitions
- the method for improving protein ion efficiency according to the present invention is characterized by including a step of introducing an organic residue derivative onto the surface of a target protein.
- R is preferably H or quaternary ammonia
- X is preferably Pt or Cu.
- composition is preferably used to improve detection sensitivity in mass spectrometry.
- the metal complex having the functional group of the present invention can be synthesized by first preparing a ligand having the functional group and then coordinating the ligand to the metal.
- the present invention also includes a protein analysis method for determining the presence or absence of a histidine residue, an arginine residue, and / or a cysteine residue in a protein using the above metal complex or composition.
- the metal complex has the following formula:
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Bioinformatics & Computational Biology (AREA)
- Organic Chemistry (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Cell Biology (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Microbiology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Food Science & Technology (AREA)
- Biotechnology (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)
- Investigating Or Analysing Biological Materials (AREA)
- Electron Tubes For Measurement (AREA)
Abstract
La présente invention concerne une protéine qui est modifiée dans des conditions modérées pour améliorer l’efficacité d’ionisation de la protéine. Un complexe métallique comprenant un groupe fonctionnel spécifique et un ligand tridenté est lié à une protéine cible. Ainsi, la protéine est détectée avec une sensibilité élevée indépendamment de la nature de la protéine.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007500466A JPWO2006080210A1 (ja) | 2005-01-27 | 2006-01-17 | イオン化効率を向上させるための試薬、方法およびキット、並びにその利用 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005019516 | 2005-01-27 | ||
JP2005-019516 | 2005-01-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006080210A1 true WO2006080210A1 (fr) | 2006-08-03 |
Family
ID=36740244
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2006/300554 WO2006080210A1 (fr) | 2005-01-27 | 2006-01-17 | Réactif, procédé et ensemble pour améliorer l'efficacité d'ionisation et leur utilisation |
Country Status (2)
Country | Link |
---|---|
JP (1) | JPWO2006080210A1 (fr) |
WO (1) | WO2006080210A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103044462A (zh) * | 2012-11-20 | 2013-04-17 | 复旦大学 | 钳型Cu(II)金属有机络合物小分子水凝胶及其应用 |
JP2015524058A (ja) * | 2012-05-22 | 2015-08-20 | バイオジェン・エムエイ・インコーポレイテッドBiogen MA Inc. | 反応性代謝物質のスクリーニングのための捕獲剤 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20200052329A (ko) * | 2017-09-08 | 2020-05-14 | 에프. 호프만-라 로슈 아게 | 질량 분석법용의 설폭사이드 기반 시약 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000226449A (ja) * | 1999-02-05 | 2000-08-15 | Agency Of Ind Science & Technol | アルキル置換フェノール重合体の製造方法 |
JP2004045292A (ja) * | 2002-07-12 | 2004-02-12 | Shimadzu Corp | 新規な金属錯体、及びそれを用いるタンパク質のアミノ酸配列決定方法 |
JP2004075633A (ja) * | 2002-08-21 | 2004-03-11 | Asahi Kasei Chemicals Corp | ヘテロポリ酸塩の製造方法 |
-
2006
- 2006-01-17 JP JP2007500466A patent/JPWO2006080210A1/ja active Pending
- 2006-01-17 WO PCT/JP2006/300554 patent/WO2006080210A1/fr not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000226449A (ja) * | 1999-02-05 | 2000-08-15 | Agency Of Ind Science & Technol | アルキル置換フェノール重合体の製造方法 |
JP2004045292A (ja) * | 2002-07-12 | 2004-02-12 | Shimadzu Corp | 新規な金属錯体、及びそれを用いるタンパク質のアミノ酸配列決定方法 |
JP2004075633A (ja) * | 2002-08-21 | 2004-03-11 | Asahi Kasei Chemicals Corp | ヘテロポリ酸塩の製造方法 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015524058A (ja) * | 2012-05-22 | 2015-08-20 | バイオジェン・エムエイ・インコーポレイテッドBiogen MA Inc. | 反応性代謝物質のスクリーニングのための捕獲剤 |
US10100081B2 (en) | 2012-05-22 | 2018-10-16 | Biogen Ma Inc. | Trapping reagents for reactive metabolites screening |
CN103044462A (zh) * | 2012-11-20 | 2013-04-17 | 复旦大学 | 钳型Cu(II)金属有机络合物小分子水凝胶及其应用 |
Also Published As
Publication number | Publication date |
---|---|
JPWO2006080210A1 (ja) | 2008-06-19 |
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