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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Classifications
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- 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
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- 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
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- G—PHYSICS
- G01—MEASURING; TESTING
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- 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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- 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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- 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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- G01N2458/00—Labels used in chemical analysis of biological material
- G01N2458/15—Non-radioactive isotope labels, e.g. for detection by mass spectrometry
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- G—PHYSICS
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2560/00—Chemical aspects of mass spectrometric analysis of biological material
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- 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
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- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/13—Tracers or tags
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- 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]
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- 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
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- 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
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- 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
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- 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)
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| JP2002-36446 | 2002-02-14 | ||
| PCT/JP2003/001463 WO2003069328A1 (en) | 2002-02-14 | 2003-02-13 | Method of analyzing aminofunctional compound and analytical reagent |
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| WO (1) | WO2003069328A1 (cg-RX-API-DMAC7.html) |
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| CA2475011C (en) * | 2002-02-14 | 2015-07-07 | Ajinomoto Co., Inc. | Method for analysis of compounds with amino group and analytical reagent therefor |
| 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 |
| US20070054345A1 (en) * | 2004-05-19 | 2007-03-08 | Hunter Christie L | Expression quantification using mass spectrometry |
| US20080206737A1 (en) * | 2004-05-19 | 2008-08-28 | Hunter Christie L | Expression quantification using mass spectrometry |
| WO2005116629A1 (ja) * | 2004-05-26 | 2005-12-08 | Ajinomoto Co., Inc. | アミノ官能性化合物の分析方法及び装置 |
| US20070048752A1 (en) | 2004-07-12 | 2007-03-01 | Applera Corporation | Mass tags for quantitative analyses |
| CA2572754A1 (en) * | 2004-07-12 | 2006-02-16 | 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 |
| 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 |
| US20110053196A1 (en) * | 2006-02-08 | 2011-03-03 | Nec Corporation | Method for modifying a peptide and a method for identifying a peptide |
| US12367163B2 (en) | 2007-06-29 | 2025-07-22 | Quest Diagnostics Investments Llc | Analysis of amino acids in body fluid by liquid chromatography—mass spectrometry |
| JP5517931B2 (ja) * | 2007-06-29 | 2014-06-11 | 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 | 液体クロマトグラフィー質量分析による体液中のアミノ酸分析 |
| JPWO2009054350A1 (ja) | 2007-10-25 | 2011-03-03 | 味の素株式会社 | 耐糖能異常の評価方法、耐糖能異常評価装置、耐糖能異常評価方法、耐糖能異常評価システム、耐糖能異常評価プログラムおよび記録媒体、ならびに耐糖能異常の予防・改善物質の探索方法 |
| US20100285593A1 (en) * | 2007-11-26 | 2010-11-11 | Waters Technologies Corporation | Internal standards and methods for use in quantitatively measuring analytes in a sample |
| WO2009100155A1 (en) * | 2008-02-04 | 2009-08-13 | Prozyme, Inc. | Compounds and methods for rapid 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 |
| US9638706B2 (en) | 2011-07-21 | 2017-05-02 | Wako Pure Chemical Industries, Ltd. | Standard solution for use in analysis of amino acid in plasma |
| EP3974412A1 (en) | 2011-09-28 | 2022-03-30 | 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 |
| US11352325B2 (en) | 2011-09-28 | 2022-06-07 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| US8916680B2 (en) | 2011-11-23 | 2014-12-23 | Quest Diagnostics Investments, Inc. | Kisspeptin-54 detection by tandem mass spectrometry |
| WO2014084290A1 (ja) | 2012-11-27 | 2014-06-05 | 味の素株式会社 | 膵臓癌の評価方法、膵臓癌評価装置、膵臓癌評価方法、膵臓癌評価プログラム、膵臓癌評価システムおよび情報通信端末装置 |
| CN107110785A (zh) * | 2014-10-30 | 2017-08-29 | 沃特世科技公司 | 快速制备标记的葡糖基胺和分析生产所述标记的葡糖基胺的糖基化生物分子的方法 |
| JP6692811B2 (ja) | 2014-11-13 | 2020-05-13 | ウオーターズ・テクノロジーズ・コーポレイシヨン | 高速でラベル化されたｎ−グリカンに対する液体クロマトグラフィー較正方法 |
| KR101627841B1 (ko) | 2015-05-27 | 2016-06-07 | 다이아텍코리아 주식회사 | 싸이오크로멘 타입 화합물 및 그 용도 |
| HUE059723T2 (hu) | 2015-05-29 | 2022-12-28 | Agilent Technologies Inc | Amintartalmú vegyületek jelölésére szolgáló vegyületek és 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 |
| US12252557B2 (en) | 2016-04-24 | 2025-03-18 | Waters Technologies Corporation | Charged surface reversed phase chromatographic materials method for analysis of glycans modified with amphipathic, strongly basic moieties |
| WO2017222954A1 (en) | 2016-06-21 | 2017-12-28 | Waters Technologies Corporation | Fluorescence tagging of glycans and other biomolecules through reductive amination for enhanced ms signals |
| US11035832B2 (en) | 2016-06-21 | 2021-06-15 | Waters Technologies Corporation | Methods of electrospray ionization of glycans modified with amphipathic, strongly basic moieties |
| CA3029144A1 (en) | 2016-06-30 | 2018-01-04 | Ajinomoto Co., Inc. | Evaluating method of ketosis in postpartum dairy cows |
| 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 |
| US20180094293A1 (en) | 2016-10-03 | 2018-04-05 | Waters Technologies Corporation | Labeled glycan amino acid complexes useful in lc-ms analysis and methods of making the same |
| WO2019048450A1 (en) * | 2017-09-08 | 2019-03-14 | Ludwig-Maximilians-Universität München | SULFOXIDE-BASED REAGENT FOR MASS SPECTROMETRY |
| JP7151723B2 (ja) | 2017-12-28 | 2022-10-12 | 味の素株式会社 | 給餌管理システムおよび給餌管理方法 |
| EP3859339A4 (en) | 2018-09-26 | 2022-12-28 | Ajinomoto Co., Inc. | METHOD FOR ASSESSING MILD COGNITIVE IMPAIRMENTS, CALCULATION METHOD, ASSESSMENT DEVICE, CALCULATION DEVICE, ASSESSMENT PROGRAM, CALCULATION PROGRAM, RECORDING MEDIA, ASSESSMENT SYSTEM AND TERMINAL |
| 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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| 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 |
| AU4173202A (en) * | 2000-10-23 | 2002-06-18 | Inst Genetics Llc | Isotope-coded ionization-enhancing reagents (icier) for high-throughput protein identification and quantitation using matrix-assisted laser desorption ionization mass spectrometry |
| EP1330654B1 (en) * | 2000-10-23 | 2006-03-08 | Genetics Institute, LLC | Acid-labile isotope-coded extractant (alice) in mass spectometric analysis |
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| 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 |
| CA2475011C (en) * | 2002-02-14 | 2015-07-07 | Ajinomoto Co., Inc. | Method for analysis of compounds with amino group and analytical reagent therefor |
| WO2005116629A1 (ja) * | 2004-05-26 | 2005-12-08 | Ajinomoto Co., Inc. | アミノ官能性化合物の分析方法及び装置 |
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| EP2317307A3 (en) | 2012-03-14 |
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| JP7055267B2 (ja) | 2022-04-18 |
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| EP2317307A2 (en) | 2011-05-04 |
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| WO2003069328A1 (en) | 2003-08-21 |
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| JP2020073916A (ja) | 2020-05-14 |
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| EP1475632B1 (en) | 2013-05-22 |
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| JP6278210B2 (ja) | 2018-02-14 |
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