JP2018052972A5 - - Google Patents
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- JP2018052972A5 JP2018052972A5 JP2017234081A JP2017234081A JP2018052972A5 JP 2018052972 A5 JP2018052972 A5 JP 2018052972A5 JP 2017234081 A JP2017234081 A JP 2017234081A JP 2017234081 A JP2017234081 A JP 2017234081A JP 2018052972 A5 JP2018052972 A5 JP 2018052972A5
- Authority
- JP
- Japan
- Prior art keywords
- labeling reagent
- compound
- amino
- mass spectrometry
- reagent according
- 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.)
- Granted
Links
- 238000002372 labelling Methods 0.000 claims description 39
- 239000003153 chemical reaction reagent Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 238000004949 mass spectrometry Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 8
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 7
- 150000001717 carbocyclic compounds Chemical group 0.000 claims description 6
- 238000004885 tandem mass spectrometry Methods 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 238000005259 measurement Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 238000002541 precursor ion scan Methods 0.000 claims description 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 2
- 238000002553 single reaction monitoring Methods 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- -1 carbamate compound Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 125000005208 trialkylammonium group Chemical group 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001601 aromatic carbocyclic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002036446 | 2002-02-14 | ||
| JP2002036446 | 2002-02-14 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015188056A Division JP6278210B2 (ja) | 2002-02-14 | 2015-09-25 | アミノ官能性化合物の分析方法及び分析試薬 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020008872A Division JP7055267B2 (ja) | 2002-02-14 | 2020-01-23 | アミノ官能性化合物の分析方法及び分析試薬 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018052972A JP2018052972A (ja) | 2018-04-05 |
| JP2018052972A5 true JP2018052972A5 (https=) | 2018-06-07 |
| JP6699645B2 JP6699645B2 (ja) | 2020-05-27 |
Family
ID=27678084
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003568398A Expired - Lifetime JP4453363B2 (ja) | 2002-02-14 | 2003-02-13 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2009269796A Expired - Lifetime JP5136542B2 (ja) | 2002-02-14 | 2009-11-27 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2012216013A Expired - Lifetime JP5842775B2 (ja) | 2002-02-14 | 2012-09-28 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2015188056A Expired - Lifetime JP6278210B2 (ja) | 2002-02-14 | 2015-09-25 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2017234081A Expired - Lifetime JP6699645B2 (ja) | 2002-02-14 | 2017-12-06 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2020008872A Expired - Lifetime JP7055267B2 (ja) | 2002-02-14 | 2020-01-23 | アミノ官能性化合物の分析方法及び分析試薬 |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003568398A Expired - Lifetime JP4453363B2 (ja) | 2002-02-14 | 2003-02-13 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2009269796A Expired - Lifetime JP5136542B2 (ja) | 2002-02-14 | 2009-11-27 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2012216013A Expired - Lifetime JP5842775B2 (ja) | 2002-02-14 | 2012-09-28 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2015188056A Expired - Lifetime JP6278210B2 (ja) | 2002-02-14 | 2015-09-25 | アミノ官能性化合物の分析方法及び分析試薬 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020008872A Expired - Lifetime JP7055267B2 (ja) | 2002-02-14 | 2020-01-23 | アミノ官能性化合物の分析方法及び分析試薬 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US7148069B2 (https=) |
| EP (3) | EP1475632B1 (https=) |
| JP (6) | JP4453363B2 (https=) |
| AU (1) | AU2003211941A1 (https=) |
| CA (1) | CA2475011C (https=) |
| WO (1) | WO2003069328A1 (https=) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP2208992A1 (en) * | 2003-11-21 | 2010-07-21 | Eisai R&D Management Co., Ltd. | Quantitation method using isotope labeled internal standard substance, analysis system for executing the quantitation method, and program for the analysis |
| 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 |
| JP5030586B2 (ja) * | 2004-05-26 | 2012-09-19 | 味の素株式会社 | アミノ官能性化合物の分析方法及び装置 |
| WO2006017208A1 (en) * | 2004-07-12 | 2006-02-16 | 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 |
| EP1983346A4 (en) * | 2006-02-08 | 2010-03-17 | Nec Corp | METHOD FOR CLEAVING A PEPTIDE BOND AT THE C-TERMINAL END OF A PEPTIDE, AND A METHOD FOR DETERMINING THE C-TERMINAL END-ACE AMINO ACID SEQUENCE OF A PEPTIDE |
| 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 |
| EP3067692B1 (en) * | 2007-06-29 | 2019-04-17 | Quest Diagnostics Investments Incorporated | Analysis of amino acids in body fluid by liquid chromatography-mass spectrometry (lc-ms) |
| WO2009054350A1 (ja) | 2007-10-25 | 2009-04-30 | Ajinomoto Co., Inc. | 耐糖能異常の評価方法 |
| WO2009070233A1 (en) * | 2007-11-26 | 2009-06-04 | Waters Technologies Corporation | Internal standards and methods for use in quantitatively measuring analytes in a sample |
| EP2252584B1 (en) | 2008-02-04 | 2016-12-07 | 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 |
| KR101968485B1 (ko) | 2011-07-21 | 2019-04-12 | 후지필름 와코 준야꾸 가부시키가이샤 | 혈장중 아미노산 분석용 표준액 |
| US10436790B2 (en) | 2011-09-28 | 2019-10-08 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| EP3974412A1 (en) | 2011-09-28 | 2022-03-30 | 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 |
| EP3557605B1 (en) | 2011-11-23 | 2021-07-14 | Quest Diagnostics Investments Incorporated | Kisspeptin-54 detection by tandem mass spectrometry |
| 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 |
| CN115753702A (zh) | 2014-10-30 | 2023-03-07 | 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 |
| US10502720B2 (en) | 2014-11-13 | 2019-12-10 | Waters Technologies Corporation | Methods for liquid chromatography calibration for rapid labeled N-glycans |
| KR101627841B1 (ko) * | 2015-05-27 | 2016-06-07 | 다이아텍코리아 주식회사 | 싸이오크로멘 타입 화합물 및 그 용도 |
| EP3304051B1 (en) | 2015-05-29 | 2020-08-26 | Agilent Technologies, Inc. | Compounds for labeling amine-containing compounds, and their use |
| 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 |
| JP7005515B2 (ja) | 2016-04-24 | 2022-02-10 | ウオーターズ・テクノロジーズ・コーポレイシヨン | 荷電表面逆相クロマトグラフィ材料による両親媒性強塩基性部分で修飾されたグリカンの分析方法 |
| WO2017222955A1 (en) | 2016-06-21 | 2017-12-28 | Waters Technologies Corporation | Methods of electrospray ionization of glycans modified with amphipathic, strongly basic moieties |
| 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 |
| 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 |
| EP3519832B1 (en) | 2016-10-03 | 2024-04-03 | Waters Technologies Corporation | Labeled glycan amino acid complexes useful in lc-ms analysis and methods of making the same |
| KR20200052329A (ko) * | 2017-09-08 | 2020-05-14 | 에프. 호프만-라 로슈 아게 | 질량 분석법용의 설폭사이드 기반 시약 |
| EP3732959A4 (en) | 2017-12-28 | 2022-03-30 | Ajinomoto Co., Inc. | POWER CONTROL SYSTEM AND METHOD OF POWER CONTROL |
| KR20250079925A (ko) | 2018-09-26 | 2025-06-04 | 아지노모토 가부시키가이샤 | 경도 인지 장애의 평가 방법, 산출 방법, 평가 장치, 산출 장치, 평가 프로그램, 산출 프로그램, 기록 매체, 평가 시스템 및 단말 장치 |
| CN116773710A (zh) * | 2021-07-13 | 2023-09-19 | 清华大学 | 一种覆盖多种代谢物的代谢组和代谢流的试剂盒和使用方法 |
| 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 |
| JPWO2024225424A1 (https=) | 2023-04-28 | 2024-10-31 |
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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 |
| US6670194B1 (en) * | 1998-08-25 | 2003-12-30 | University Of Washington | Rapid quantitative analysis of proteins or protein function in complex mixtures |
| 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 |
| US6677114B1 (en) * | 1999-04-20 | 2004-01-13 | Target Discovery, Inc. | Polypeptide fingerprinting methods and bioinformatics database system |
| 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 |
| JP4212353B2 (ja) * | 2000-07-11 | 2009-01-21 | 財団法人神奈川科学技術アカデミー | 液状試料の質量分析用プローブ |
| 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 |
| JP4141834B2 (ja) * | 2000-10-23 | 2008-08-27 | ジェネティックス インスティテュート エルエルシー | マトリックス支援レーザー脱離イオン化マススペクトロメトリーを使用したハイスループットなタンパク質の同定及び定量のための同位体コードイオン化増強試薬（ｉｃｉｅｒ） |
| AU4338502A (en) * | 2000-10-23 | 2002-06-24 | Genetics Inst | Acid-labile isotope-coded extractant (alice) and its use in quantitative mass spectrometric analysis of protein mixtures |
| 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 |
| JP5030586B2 (ja) | 2004-05-26 | 2012-09-19 | 味の素株式会社 | アミノ官能性化合物の分析方法及び装置 |
-
2003
- 2003-02-13 AU AU2003211941A patent/AU2003211941A1/en not_active Abandoned
- 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
- 2003-02-13 WO PCT/JP2003/001463 patent/WO2003069328A1/ja not_active Ceased
- 2003-02-13 CA CA2475011A patent/CA2475011C/en not_active Expired - Lifetime
- 2003-02-13 EP EP10012964A patent/EP2336763A1/en not_active Withdrawn
- 2003-02-13 EP EP10012963.4A patent/EP2317307B1/en not_active Expired - Lifetime
-
2004
- 2004-08-16 US US10/918,380 patent/US7148069B2/en not_active Expired - Lifetime
-
2006
- 2006-09-01 US US11/514,130 patent/US9274123B2/en not_active Expired - Fee Related
-
2009
- 2009-11-27 JP JP2009269796A patent/JP5136542B2/ja not_active Expired - Lifetime
-
2012
- 2012-09-28 JP JP2012216013A patent/JP5842775B2/ja not_active Expired - Lifetime
-
2015
- 2015-09-25 JP JP2015188056A patent/JP6278210B2/ja not_active Expired - Lifetime
-
2016
- 2016-01-21 US US15/003,235 patent/US9658234B2/en not_active Expired - Lifetime
-
2017
- 2017-12-06 JP JP2017234081A patent/JP6699645B2/ja not_active Expired - Lifetime
-
2020
- 2020-01-23 JP JP2020008872A patent/JP7055267B2/ja not_active Expired - Lifetime
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