CA3007430C - Isobaric mass labels - Google Patents
Isobaric mass labels Download PDFInfo
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- CA3007430C CA3007430C CA3007430A CA3007430A CA3007430C CA 3007430 C CA3007430 C CA 3007430C CA 3007430 A CA3007430 A CA 3007430A CA 3007430 A CA3007430 A CA 3007430A CA 3007430 C CA3007430 C CA 3007430C
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- 239000012491 analyte Substances 0.000 claims abstract description 40
- 239000003607 modifier Substances 0.000 claims abstract description 27
- 238000004949 mass spectrometry Methods 0.000 claims abstract description 26
- 150000002500 ions Chemical class 0.000 claims description 77
- 238000000034 method Methods 0.000 claims description 37
- 238000001819 mass spectrum Methods 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 239000012634 fragment Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 238000004458 analytical method Methods 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 230000000295 complement effect Effects 0.000 claims description 10
- 238000001360 collision-induced dissociation Methods 0.000 claims description 7
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- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
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- 230000007935 neutral effect Effects 0.000 claims description 3
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- -1 2,3,5,6-tetrafluorophenyl ester Chemical class 0.000 description 12
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- JSSXHAMIXJGYCS-UHFFFAOYSA-N piperazin-4-ium-2-carboxylate Chemical class OC(=O)C1CNCCN1 JSSXHAMIXJGYCS-UHFFFAOYSA-N 0.000 description 11
- 238000013467 fragmentation Methods 0.000 description 10
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- 230000000155 isotopic effect Effects 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 9
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- 125000003277 amino group Chemical group 0.000 description 9
- 229910052805 deuterium Inorganic materials 0.000 description 9
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- NSUDGNLOXMLAEB-UHFFFAOYSA-N 5-(2-formyl-3-hydroxyphenoxy)pentanoic acid Chemical compound OC(=O)CCCCOC1=CC=CC(O)=C1C=O NSUDGNLOXMLAEB-UHFFFAOYSA-N 0.000 description 6
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
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- 238000004885 tandem mass spectrometry Methods 0.000 description 6
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- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 5
- 125000004431 deuterium atom Chemical group 0.000 description 5
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 5
- 238000006485 reductive methylation reaction Methods 0.000 description 5
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 150000003573 thiols Chemical class 0.000 description 5
- UCFZVQHKTRSZMM-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)benzoic acid Chemical compound C1CN(C)CCN1C1=CC=C(C(O)=O)C=C1 UCFZVQHKTRSZMM-UHFFFAOYSA-N 0.000 description 4
- 125000006847 BOC protecting group Chemical group 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 4
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- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 4
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 4
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 4
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 4
- 239000004473 Threonine Substances 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000004279 alanine Nutrition 0.000 description 4
- 238000003491 array Methods 0.000 description 4
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000013461 design Methods 0.000 description 4
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 238000001211 electron capture detection Methods 0.000 description 4
- 238000001077 electron transfer detection Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000007857 hydrazones Chemical class 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- GFRDSYFROJUKBF-UHFFFAOYSA-N n-diazoimidazole-1-sulfonamide Chemical compound [N-]=[N+]=NS(=O)(=O)N1C=CN=C1 GFRDSYFROJUKBF-UHFFFAOYSA-N 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
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- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
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- G01N33/6893—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids related to diseases not provided for elsewhere
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- 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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- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
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Landscapes
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| PCT/EP2016/080534 WO2017098029A1 (en) | 2015-12-11 | 2016-12-09 | Isobaric mass labels |
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| CN110297056A (zh) * | 2019-06-29 | 2019-10-01 | 南京谱利健生物技术有限公司 | 一种同量异位标签试剂的制备及应用 |
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| US8362242B2 (en) * | 2006-06-30 | 2013-01-29 | Dh Technologies Development Pte. Ltd. | Analyte determination utilizing mass tagging reagents comprising a non-encoded detectable label |
| US7906341B2 (en) * | 2006-06-30 | 2011-03-15 | Dh Technologies Development Pte, Ltd. | Methods, mixtures, kits and compositions pertaining to analyte determination |
| EP1918714A1 (en) * | 2006-11-02 | 2008-05-07 | Koninklijke Philips Electronics N.V. | Compounds and methods for double labelling of polypeptides to allow multiplexing in mass spectrometric analysis |
| GB0811298D0 (en) * | 2008-06-19 | 2008-07-30 | Trillion Genomics Ltd | Characterising polypeptides |
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| EP2373977A1 (en) * | 2008-12-17 | 2011-10-12 | The Lubrizol Corporation | Optically active functional fluid markers |
| US8486712B2 (en) * | 2009-03-10 | 2013-07-16 | University Of Maryland, College Park | Deuterium isobaric tag reagents for quantitative analysis |
| US20110003395A1 (en) * | 2009-05-31 | 2011-01-06 | Dh Technologies Development Pte. Ltd. | Specific analysis of analytes using reagent compounds, labeling strategies, and mass spectrometry workflow |
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| WO2013138210A1 (en) | 2012-03-14 | 2013-09-19 | Ning Xi | Substituted cyclic compounds and methods of use |
| EP2847594B1 (en) * | 2012-05-10 | 2016-06-22 | Thermo Finnigan LLC | Method for highly multiplexed quantitation of peptides by mass spectrometry and labeling reagent sets therefor |
| US9835629B2 (en) * | 2012-05-18 | 2017-12-05 | Pierce Biotechnology, Inc. | Methods and reagents for biomolecule labeling, enrichment and gentle elution |
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- 2016-12-09 JP JP2018529642A patent/JP6793196B2/ja active Active
- 2016-12-09 CA CA3007430A patent/CA3007430C/en active Active
- 2016-12-09 US US16/061,136 patent/US11453621B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN108463728A (zh) | 2018-08-28 |
| US11453621B2 (en) | 2022-09-27 |
| CA3007430A1 (en) | 2017-06-15 |
| JP2019505764A (ja) | 2019-02-28 |
| JP6793196B2 (ja) | 2020-12-02 |
| CN108463728B (zh) | 2023-03-24 |
| EP3387445B1 (en) | 2023-02-08 |
| WO2017098029A1 (en) | 2017-06-15 |
| US20180362416A1 (en) | 2018-12-20 |
| GB201521903D0 (en) | 2016-01-27 |
| EP3387445A1 (en) | 2018-10-17 |
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