CA2475011C - Method for analysis of compounds with amino group and analytical reagent therefor - Google Patents
Method for analysis of compounds with amino group and analytical reagent therefor Download PDFInfo
- Publication number
- CA2475011C CA2475011C CA2475011A CA2475011A CA2475011C CA 2475011 C CA2475011 C CA 2475011C CA 2475011 A CA2475011 A CA 2475011A CA 2475011 A CA2475011 A CA 2475011A CA 2475011 C CA2475011 C CA 2475011C
- Authority
- CA
- Canada
- Prior art keywords
- group
- compound
- carbamate
- reagent
- amino group
- 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.)
- Expired - Lifetime
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- 125000003277 amino group Chemical group 0.000 title claims abstract description 99
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- 238000004949 mass spectrometry Methods 0.000 claims abstract description 29
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
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- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- 235000013930 proline Nutrition 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229960002898 threonine Drugs 0.000 description 1
- 235000008521 threonine Nutrition 0.000 description 1
- INQOMBQAUSQDDS-FIBGUPNXSA-N trideuterio(iodo)methane Chemical compound [2H]C([2H])([2H])I INQOMBQAUSQDDS-FIBGUPNXSA-N 0.000 description 1
- 229960004441 tyrosine Drugs 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- G—PHYSICS
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- 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
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
-
- 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
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- 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
- G01N33/6806—Determination of free amino acids
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- 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
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2458/00—Labels used in chemical analysis of biological material
- G01N2458/15—Non-radioactive isotope labels, e.g. for detection by mass spectrometry
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2560/00—Chemical aspects of mass spectrometric analysis of biological material
-
- 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
- Y10T436/13—Tracers or tags
-
- 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
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
-
- 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
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/145555—Hetero-N
-
- 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)
- Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Physics & Mathematics (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pathology (AREA)
- Food Science & Technology (AREA)
- Cell Biology (AREA)
- Biotechnology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Bioinformatics & Computational Biology (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002-36446 | 2002-02-14 | ||
| JP2002036446 | 2002-02-14 | ||
| PCT/JP2003/001463 WO2003069328A1 (en) | 2002-02-14 | 2003-02-13 | Method of analyzing aminofunctional compound and analytical reagent |
Publications (2)
| Publication Number | Publication Date |
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| CA2475011A1 CA2475011A1 (en) | 2003-08-21 |
| CA2475011C true CA2475011C (en) | 2015-07-07 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2475011A Expired - Lifetime CA2475011C (en) | 2002-02-14 | 2003-02-13 | Method for analysis of compounds with amino group and analytical reagent therefor |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US7148069B2 (OSRAM) |
| EP (3) | EP1475632B1 (OSRAM) |
| JP (6) | JP4453363B2 (OSRAM) |
| AU (1) | AU2003211941A1 (OSRAM) |
| CA (1) | CA2475011C (OSRAM) |
| WO (1) | WO2003069328A1 (OSRAM) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| AU2003211941A1 (en) * | 2002-02-14 | 2003-09-04 | Ajinomoto Co., Inc. | Method of analyzing aminofunctional compound and analytical reagent |
| US20050014279A1 (en) * | 2003-07-14 | 2005-01-20 | Nguyen Hoa Duc | Method of analysis of amine by mass spectrometry |
| EP1686372A4 (en) * | 2003-11-21 | 2009-04-01 | Eisai R&D Man Co Ltd | QUANTIFICATION METHOD USING AN ISOTOPE-MARKED INTERNAL CALIBRATION, ANALYSIS SYSTEM FOR EXECUTING THE QUANTIFICATION METHOD AND ASSOCIATED SEPARATION PROGRAM |
| US20080206737A1 (en) * | 2004-05-19 | 2008-08-28 | Hunter Christie L | Expression quantification using mass spectrometry |
| US20070054345A1 (en) * | 2004-05-19 | 2007-03-08 | Hunter Christie L | Expression quantification using mass spectrometry |
| EP1750126B1 (en) * | 2004-05-26 | 2015-09-16 | Ajinomoto Co., Inc. | Method and apparatus for analyzing aminofunctional compound |
| EP1776588A1 (en) * | 2004-07-12 | 2007-04-25 | Applera Corporation | Mass tags for quantitative analyses |
| US20070048752A1 (en) | 2004-07-12 | 2007-03-01 | Applera Corporation | Mass tags for quantitative analyses |
| US8969089B2 (en) | 2004-10-12 | 2015-03-03 | Quest Diagnostics Investments, Inc. | Analysis of amino acids in body fluid by liquid chromatography-mass spectrometry |
| US20060183238A1 (en) | 2005-02-09 | 2006-08-17 | Applera Corporation | Amine-containing compound analysis methods |
| JP2007163423A (ja) * | 2005-12-16 | 2007-06-28 | Ajinomoto Co Inc | 質量分析計によるアミノ酸分析方法 |
| EP1982991A4 (en) * | 2006-02-08 | 2009-10-21 | Nec Corp | PROCESS FOR MODIFYING PEPTIDE AND METHOD FOR IDENTIFYING PEPTIDE |
| JP4771296B2 (ja) * | 2006-02-08 | 2011-09-14 | 日本電気株式会社 | ペプチドのｃ末端のペプチド結合を切断する方法、及びペプチドのｃ末端アミノ酸配列の決定方法 |
| CA2691974C (en) * | 2007-06-29 | 2016-08-30 | Quest Diagnostics Investments Incorporated | Analysis of amino acids in body fluid by liquid chromatography-mass spectrometry |
| US12367163B2 (en) | 2007-06-29 | 2025-07-22 | Quest Diagnostics Investments Llc | Analysis of amino acids in body fluid by liquid chromatography—mass spectrometry |
| EP2209001A4 (en) | 2007-10-25 | 2010-10-27 | Ajinomoto Kk | METHOD FOR ASSESSING STROKEN GLUCOSE TOLERANCE |
| EP2215460A4 (en) * | 2007-11-26 | 2010-12-29 | Waters Technologies Corp | INTERNAL STANDARDS AND METHODS FOR USE IN MEASURING QUANTITATIVELY ANALYTES IN A SAMPLE |
| DK2252584T3 (en) | 2008-02-04 | 2017-01-16 | Prozyme Inc | COMPOUNDS AND PROCEDURES FOR QUICK LABELING OF N-GLYCANS |
| DE102009060102A1 (de) * | 2009-12-21 | 2011-06-22 | Martin-Luther-Universität Halle-Wittenberg, 06108 | Derivatisierungsreagenzien zur tandem-massenspektrometrischen Quantifizierung von Proteinen |
| JP6072686B2 (ja) | 2011-07-21 | 2017-02-01 | 和光純薬工業株式会社 | 血漿中アミノ酸分析用標準液 |
| JP6193237B2 (ja) | 2011-09-28 | 2017-09-06 | ウオーターズ・テクノロジーズ・コーポレイシヨン | 強められたｍｓ信号を有するグリカンおよび他の生体分子の迅速蛍光タグ付け |
| US11352325B2 (en) | 2011-09-28 | 2022-06-07 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| US10436790B2 (en) | 2011-09-28 | 2019-10-08 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| JP6444736B2 (ja) | 2011-11-23 | 2018-12-26 | クエスト ダイアグノスティックス インヴェストメンツ インコーポレイテッド | タンデム質量分析によるキスペプチン−５４の検出 |
| KR101824937B1 (ko) | 2012-11-27 | 2018-02-02 | 아지노모토 가부시키가이샤 | 췌장암의 평가 방법, 췌장암 평가 장치, 췌장암 평가 방법, 췌장암 평가 프로그램, 췌장암 평가 시스템 및 정보 통신 단말 장치 |
| DK3213056T3 (da) * | 2014-10-30 | 2020-09-28 | Waters Technologies Corp | Fremgangsmåder til hurtig forberedelse af mærkede glycosylaminer og til analyse af glykosylerede biomolekyler, som giver samme baggrund |
| CN107108465B (zh) | 2014-11-13 | 2020-08-04 | 沃特世科技公司 | 快速标记的n-聚糖的液相色谱校准方法 |
| KR101627841B1 (ko) * | 2015-05-27 | 2016-06-07 | 다이아텍코리아 주식회사 | 싸이오크로멘 타입 화합물 및 그 용도 |
| HUE052637T2 (hu) | 2015-05-29 | 2021-05-28 | Agilent Technologies Inc | Olyan vegyületek melyek amin-tartalmú vegyületek jelölésére szolgálnak és ezeknek a felhasználásuk |
| CN105548432A (zh) * | 2015-12-18 | 2016-05-04 | 乐普药业股份有限公司 | 一种比伐卢定中氨基酸的检测分析方法 |
| CN117054585A (zh) | 2016-04-24 | 2023-11-14 | 沃特世科技公司 | 用于对用两亲强碱性部分改性的聚糖进行分析的带电表面反相色谱材料方法 |
| US11061023B2 (en) | 2016-06-21 | 2021-07-13 | Waters Technologies Corporation | Fluorescence tagging of glycans and other biomolecules through reductive amination for enhanced MS signals |
| CN109642906A (zh) | 2016-06-21 | 2019-04-16 | 沃特世科技公司 | 对用两亲强碱性部分改性的聚糖进行电喷雾电离的方法 |
| CN109313203B (zh) | 2016-06-30 | 2023-01-06 | 味之素株式会社 | 分娩后酮病的评价方法 |
| EP3479103B1 (en) | 2016-07-01 | 2022-04-20 | Waters Technologies Corporation | Methods for the rapid preparation of labeled glycosylamines from complex matrices using molecular weight cut off filtration and on-filter deglycosylation |
| WO2018067398A1 (en) | 2016-10-03 | 2018-04-12 | Waters Technologies Corporation | Labeled glycan amino acid complexes useful in lc-ms analysis and methods of making the same |
| EP3692372B1 (en) * | 2017-09-08 | 2024-04-17 | F. Hoffmann-La Roche AG | Sulfoxide-based reagent for mass spectrometry |
| WO2019130920A1 (ja) | 2017-12-28 | 2019-07-04 | 味の素株式会社 | 給餌管理システムおよび給餌管理方法 |
| JP7424297B2 (ja) | 2018-09-26 | 2024-01-30 | 味の素株式会社 | 取得方法、算出方法、評価装置、算出装置、評価プログラム、算出プログラム、記録媒体、評価システム |
| CN113624862B (zh) * | 2021-07-13 | 2023-04-07 | 清华大学 | 一种覆盖多种代谢物的代谢组和代谢流分析方法和试剂盒 |
| CN114354801B (zh) * | 2021-12-31 | 2023-07-18 | 山东大学 | （R）-3-Boc-氨基哌啶中三种氨基吡啶异构体含量的分析方法 |
| CN115925614B (zh) * | 2022-12-02 | 2024-03-08 | 中山大学 | 用于发现可与醛基反应的活性物质的小分子探针 |
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| US4003912A (en) * | 1973-06-11 | 1977-01-18 | Monsanto Company | Dicarboximido-N-phenylsubstituted carbamates and derivatives |
| JPS5855754A (ja) | 1981-09-30 | 1983-04-02 | Hitachi Ltd | アミノ酸分析方法 |
| JPS6444848A (en) | 1987-08-14 | 1989-02-17 | Hitachi Ltd | Analysis of amino acid |
| US5296599A (en) | 1991-09-19 | 1994-03-22 | Millipore Corporation | Activated carbamates compounds |
| AU687109B2 (en) * | 1994-07-08 | 1998-02-19 | City Of Hope | N-terminal protein sequencing reagents and methods which form amino acid derivatives |
| JP3346965B2 (ja) | 1995-09-14 | 2002-11-18 | 株式会社日立製作所 | アミノ酸分析装置 |
| TW358097B (en) * | 1996-05-24 | 1999-05-11 | Hoffmann La Roche | Beta-lactams and their process and pharmaceutical compositions |
| JP4085443B2 (ja) | 1997-05-07 | 2008-05-14 | 株式会社島津製作所 | アミノ酸の分析試薬及びアミノ酸の分析方法 |
| US6379971B1 (en) * | 1998-02-24 | 2002-04-30 | Target Discovery, Inc. | Methods for sequencing proteins |
| ATE536422T1 (de) * | 1998-08-25 | 2011-12-15 | Univ Washington | Schnelle quantitative analyse von proteinen oder proteinfunktionen in komplexen gemischen |
| GB9821393D0 (en) | 1998-10-01 | 1998-11-25 | Brax Genomics Ltd | Protein profiling 2 |
| US6629040B1 (en) * | 1999-03-19 | 2003-09-30 | University Of Washington | Isotope distribution encoded tags for protein identification |
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| JP4505905B2 (ja) | 1999-11-22 | 2010-07-21 | 住友化学株式会社 | ペプチドのアミノ酸配列決定方法 |
| JP3341041B2 (ja) * | 2000-02-23 | 2002-11-05 | 独立行政法人産業技術総合研究所 | ペプチドのアミノ酸配列解析方法 |
| AUPQ664300A0 (en) * | 2000-04-03 | 2000-05-04 | Proteome Systems Ltd | Macromolecule detection |
| US6716634B1 (en) * | 2000-05-31 | 2004-04-06 | Agilent Technologies, Inc. | Increasing ionization efficiency in mass spectrometry |
| US7301018B2 (en) * | 2000-07-11 | 2007-11-27 | Japan Science And Technology Corporation | Probe for mass spectrometry of liquid sample |
| US20060141632A1 (en) | 2000-07-25 | 2006-06-29 | The Procter & Gamble Co. | New methods and kits for sequencing polypeptides |
| JP3508710B2 (ja) | 2000-09-01 | 2004-03-22 | 株式会社日立製作所 | アミノ酸分析方法および装置 |
| AU2002243385C1 (en) * | 2000-10-23 | 2008-07-24 | Genetics Institute, Llc | Acid-labile isotope-coded extractant (ALICE) in mass spectrometric analysis |
| AU2002241732B2 (en) * | 2000-10-23 | 2007-07-12 | Genetics Institute, Llc | Isotope-coded ionization-enhancing reagents (ICIER) for high-throughput protein identification and quantitation using matrix-assisted laser desorption ionization mass spectrometry |
| US20030045552A1 (en) * | 2000-12-27 | 2003-03-06 | Robarge Michael J. | Isoindole-imide compounds, compositions, and uses thereof |
| US6818454B2 (en) * | 2001-02-16 | 2004-11-16 | Battelle Memorial Institute | Phosphoprotein binding agents and methods of their use |
| JP3464665B2 (ja) | 2002-01-07 | 2003-11-10 | 株式会社日立製作所 | アミノ酸分析装置 |
| AU2003211941A1 (en) | 2002-02-14 | 2003-09-04 | Ajinomoto Co., Inc. | Method of analyzing aminofunctional compound and analytical reagent |
| EP1750126B1 (en) * | 2004-05-26 | 2015-09-16 | Ajinomoto Co., Inc. | Method and apparatus for analyzing aminofunctional compound |
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- 2003-02-13 EP EP03705088.7A patent/EP1475632B1/en not_active Expired - Lifetime
- 2003-02-13 JP JP2003568398A patent/JP4453363B2/ja not_active Expired - Lifetime
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- 2003-02-13 EP EP10012964A patent/EP2336763A1/en not_active Withdrawn
- 2003-02-13 WO PCT/JP2003/001463 patent/WO2003069328A1/ja not_active Ceased
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- 2009-11-27 JP JP2009269796A patent/JP5136542B2/ja not_active Expired - Lifetime
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2020
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| EP2336763A1 (en) | 2011-06-22 |
| US7148069B2 (en) | 2006-12-12 |
| EP2317307A2 (en) | 2011-05-04 |
| AU2003211941A1 (en) | 2003-09-04 |
| EP2317307B1 (en) | 2013-11-20 |
| JP6278210B2 (ja) | 2018-02-14 |
| EP1475632A4 (en) | 2008-06-25 |
| JP5842775B2 (ja) | 2016-01-13 |
| US20060286673A1 (en) | 2006-12-21 |
| CA2475011A1 (en) | 2003-08-21 |
| US20050079624A1 (en) | 2005-04-14 |
| US20160139134A1 (en) | 2016-05-19 |
| JP4453363B2 (ja) | 2010-04-21 |
| JP6699645B2 (ja) | 2020-05-27 |
| JP5136542B2 (ja) | 2013-02-06 |
| JP2013015537A (ja) | 2013-01-24 |
| US9274123B2 (en) | 2016-03-01 |
| JP7055267B2 (ja) | 2022-04-18 |
| US9658234B2 (en) | 2017-05-23 |
| JP2016029068A (ja) | 2016-03-03 |
| JP2018052972A (ja) | 2018-04-05 |
| JP2020073916A (ja) | 2020-05-14 |
| JPWO2003069328A1 (ja) | 2005-06-09 |
| EP1475632B1 (en) | 2013-05-22 |
| WO2003069328A1 (en) | 2003-08-21 |
| EP2317307A3 (en) | 2012-03-14 |
| JP2010071995A (ja) | 2010-04-02 |
| EP1475632A1 (en) | 2004-11-10 |
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