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
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 157
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 127
- 125000003277 amino group Chemical group 0.000 title claims abstract description 99
- 238000000034 method Methods 0.000 title claims abstract description 90
- 238000004458 analytical method Methods 0.000 title abstract description 85
- 150000001413 amino acids Chemical class 0.000 claims abstract description 122
- 238000002372 labelling Methods 0.000 claims abstract description 88
- -1 carbamate compound Chemical class 0.000 claims abstract description 76
- 238000004949 mass spectrometry Methods 0.000 claims abstract description 29
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 13
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000005412 pyrazyl group Chemical class 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 9
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004076 pyridyl group Chemical class 0.000 claims description 7
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 abstract description 22
- 238000004885 tandem mass spectrometry Methods 0.000 abstract description 14
- 229940024606 amino acid Drugs 0.000 description 120
- 235000001014 amino acid Nutrition 0.000 description 120
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 63
- 150000002500 ions Chemical class 0.000 description 61
- 239000012634 fragment Substances 0.000 description 32
- 239000000203 mixture Substances 0.000 description 31
- 238000004128 high performance liquid chromatography Methods 0.000 description 27
- 239000000126 substance Substances 0.000 description 27
- 238000005259 measurement Methods 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 23
- MEYZIGGCNFHINA-UHFFFAOYSA-N (6-aminoquinolin-2-yl) n-(2,5-dioxopyrrolidin-1-yl)-n-hydroxycarbamate Chemical compound C1=CC2=CC(N)=CC=C2N=C1OC(=O)N(O)N1C(=O)CCC1=O MEYZIGGCNFHINA-UHFFFAOYSA-N 0.000 description 22
- 125000001624 naphthyl group Chemical group 0.000 description 21
- 238000000926 separation method Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 238000001514 detection method Methods 0.000 description 18
- 238000002545 neutral loss scan Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 238000002553 single reaction monitoring Methods 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 12
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 238000002541 precursor ion scan Methods 0.000 description 11
- 230000007935 neutral effect Effects 0.000 description 10
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 9
- 239000008186 active pharmaceutical agent Substances 0.000 description 8
- 150000001717 carbocyclic compounds Chemical class 0.000 description 8
- 150000002391 heterocyclic compounds Chemical group 0.000 description 8
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 8
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 8
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 7
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 7
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 7
- 238000003776 cleavage reaction Methods 0.000 description 7
- 230000007017 scission Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 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 6
- 238000001360 collision-induced dissociation Methods 0.000 description 6
- 238000012937 correction Methods 0.000 description 6
- 229960005190 phenylalanine Drugs 0.000 description 6
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 5
- OVCWIANTUTZFIY-UHFFFAOYSA-N 3-(6-aminoquinolin-2-yl)-1-hydroxypyrrolidine-2,5-dione;carbamic acid Chemical compound NC(O)=O.C1=CC2=CC(N)=CC=C2N=C1C1CC(=O)N(O)C1=O OVCWIANTUTZFIY-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000000413 hydrolysate Substances 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229940117953 phenylisothiocyanate Drugs 0.000 description 4
- 125000005493 quinolyl group Chemical group 0.000 description 4
- AEXTYZFQKYIOQP-UHFFFAOYSA-N (3-aminopyridin-2-yl) carbamate Chemical compound NC(=O)OC1=NC=CC=C1N AEXTYZFQKYIOQP-UHFFFAOYSA-N 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- PGZIDERTDJHJFY-UHFFFAOYSA-N 4-fluoro-7-nitro-2,1,3-benzoxadiazole Chemical compound [O-][N+](=O)C1=CC=C(F)C2=NON=C12 PGZIDERTDJHJFY-UHFFFAOYSA-N 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001351 alkyl iodides Chemical class 0.000 description 3
- 239000012491 analyte Substances 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000007850 fluorescent dye Substances 0.000 description 3
- 238000001215 fluorescent labelling Methods 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 229940054441 o-phthalaldehyde Drugs 0.000 description 3
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 230000004304 visual acuity Effects 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
- DDRLBMPTYVXCLK-UHFFFAOYSA-N 3-(9-aminoacridin-1-yl)-1-hydroxypyrrolidine-2,5-dione;carbamic acid Chemical compound NC(O)=O.C=12C(N)=C3C=CC=CC3=NC2=CC=CC=1C1CC(=O)N(O)C1=O DDRLBMPTYVXCLK-UHFFFAOYSA-N 0.000 description 2
- UGXJJUSLMZKOLF-UHFFFAOYSA-N 4-hydrazinyl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(NN)C=C1 UGXJJUSLMZKOLF-UHFFFAOYSA-N 0.000 description 2
- XPDXVDYUQZHFPV-UHFFFAOYSA-N Dansyl Chloride Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(Cl)(=O)=O XPDXVDYUQZHFPV-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 2
- NSTPXGARCQOSAU-VIFPVBQESA-N N-formyl-L-phenylalanine Chemical compound O=CN[C@H](C(=O)O)CC1=CC=CC=C1 NSTPXGARCQOSAU-VIFPVBQESA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002540 product ion scan Methods 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- IROZWDOFMQNCIX-UHFFFAOYSA-N (2-aminopyridin-3-yl) carbamate Chemical compound NC(=O)OC1=CC=CN=C1N IROZWDOFMQNCIX-UHFFFAOYSA-N 0.000 description 1
- UEUIKXVPXLWUDU-UHFFFAOYSA-N 4-diazoniobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 101100228206 Caenorhabditis elegans gly-6 gene Proteins 0.000 description 1
- 101100315627 Caenorhabditis elegans tyr-3 gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 description 1
- 238000000018 DNA microarray Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 101000581940 Homo sapiens Napsin-A Proteins 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- 125000002061 L-isoleucyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])[C@](C([H])([H])[H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 102100027343 Napsin-A Human genes 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- PPODYLJWPADBRJ-UHFFFAOYSA-N [2-(2,5-dioxopyrrolidin-1-yl)phenyl] carbamate Chemical compound NC(=O)OC1=CC=CC=C1N1C(=O)CCC1=O PPODYLJWPADBRJ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229960003767 alanine Drugs 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229960005261 aspartic acid Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 229960005274 benzocaine Drugs 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 238000002795 fluorescence method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 229960002885 histidine Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 229960003136 leucine Drugs 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 229960004452 methionine Drugs 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 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
-
- 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
- G01N33/58—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
-
- 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
-
- 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
-
- 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)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Physics & Mathematics (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pathology (AREA)
- Bioinformatics & Computational Biology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Analytical Chemistry (AREA)
- Cell Biology (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (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 |
|---|---|---|---|
| JP2002036446 | 2002-02-14 | ||
| JP2002-36446 | 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 |
|---|---|
| CA2475011A1 CA2475011A1 (en) | 2003-08-21 |
| CA2475011C true CA2475011C (en) | 2015-07-07 |
Family
ID=27678084
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 (show.php) |
| EP (3) | EP2317307B1 (show.php) |
| JP (6) | JP4453363B2 (show.php) |
| AU (1) | AU2003211941A1 (show.php) |
| CA (1) | CA2475011C (show.php) |
| WO (1) | WO2003069328A1 (show.php) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4453363B2 (ja) | 2002-02-14 | 2010-04-21 | 味の素株式会社 | アミノ官能性化合物の分析方法及び分析試薬 |
| US20050014279A1 (en) * | 2003-07-14 | 2005-01-20 | Nguyen Hoa Duc | Method of analysis of amine by mass spectrometry |
| US7759130B2 (en) * | 2003-11-21 | 2010-07-20 | Eisai R & D Management Co., Ltd. | Mass spectrometric quantitation method for biomolecules based on metabolically labeled internal standards |
| 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 |
| 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 |
| CN104076100A (zh) * | 2007-06-29 | 2014-10-01 | 奎斯特诊断投资公司 | 用液相层析-质谱法分析体液内的氨基酸 |
| EP2209001A4 (en) | 2007-10-25 | 2010-10-27 | Ajinomoto Kk | METHOD FOR ASSESSING STROKEN GLUCOSE TOLERANCE |
| JP2011504596A (ja) * | 2007-11-26 | 2011-02-10 | ウオーターズ・テクノロジーズ・コーポレイシヨン | サンプル中の分析物を定量測定する際に使用するための内部標準および方法 |
| US8124792B2 (en) | 2008-02-04 | 2012-02-28 | 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 |
| KR102002770B1 (ko) | 2011-07-21 | 2019-07-24 | 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 |
| US11352325B2 (en) | 2011-09-28 | 2022-06-07 | 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 |
| 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 |
| JP6269502B2 (ja) | 2012-11-27 | 2018-01-31 | 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端末装置 |
| EP3748340B1 (en) | 2014-10-30 | 2022-04-06 | Waters Technologies Corporation | Methods for the rapid preparation of labeled glycosylamines and for the analysis of glycosylated biomolecules producing the same |
| CN111796039B (zh) | 2014-11-13 | 2023-03-17 | 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 |
| WO2016196311A1 (en) | 2015-05-29 | 2016-12-08 | Prozyme, 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 |
| 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 |
| US11035832B2 (en) | 2016-06-21 | 2021-06-15 | Waters Technologies Corporation | Methods of electrospray ionization of glycans modified with amphipathic, strongly basic moieties |
| EP3472132A4 (en) | 2016-06-21 | 2020-01-15 | Waters Technologies Corporation | FLUORESCENCE LABELING OF GLYCANS AND OTHER BIOMOLECULES BY REDUCING AMINATION FOR IMPROVED MASS SPECTROMETRY SIGNALS |
| PT3480599T (pt) | 2016-06-30 | 2024-10-18 | Ajinomoto Kk | Método de avaliação da cetose pós-parto |
| 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 |
| BR112020004444A2 (pt) * | 2017-09-08 | 2020-09-15 | F. Hoffmann-La Roche Ag | reagente à base de sulfóxido para espectrometria de massa |
| CA3086986A1 (en) | 2017-12-28 | 2019-07-04 | Ajinomoto Co., Inc. | Feeding management system and feeding management method |
| KR20210064340A (ko) | 2018-09-26 | 2021-06-02 | 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 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5807748A (en) * | 1994-07-08 | 1998-09-15 | City Of Hope | N-terminal protein sequencing reagents and methods which form amino acid detectable by a variety of techniques |
| 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 |
| DE69912444T3 (de) * | 1998-08-25 | 2010-05-06 | University Of Washington, Seattle | 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 |
| 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 |
| AU2001269491A1 (en) * | 2000-07-11 | 2002-01-21 | 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 |
| 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 |
| DE60117849T2 (de) * | 2000-10-23 | 2006-09-21 | Genetics Institute, LLC, Cambridge | Säureempfindliches isotop-codiertes extrahiermittel (alice) in massenspectrometrieanalyse |
| 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 |
| JP4453363B2 (ja) | 2002-02-14 | 2010-04-21 | 味の素株式会社 | アミノ官能性化合物の分析方法及び分析試薬 |
| 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 JP JP2003568398A patent/JP4453363B2/ja not_active Expired - Lifetime
- 2003-02-13 EP EP10012963.4A patent/EP2317307B1/en not_active Expired - Lifetime
- 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 AU AU2003211941A patent/AU2003211941A1/en not_active Abandoned
- 2003-02-13 EP EP03705088.7A patent/EP1475632B1/en not_active Expired - Lifetime
- 2003-02-13 WO PCT/JP2003/001463 patent/WO2003069328A1/ja not_active Ceased
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003069328A1 (en) | 2003-08-21 |
| JPWO2003069328A1 (ja) | 2005-06-09 |
| JP2016029068A (ja) | 2016-03-03 |
| JP5136542B2 (ja) | 2013-02-06 |
| JP7055267B2 (ja) | 2022-04-18 |
| EP2317307A2 (en) | 2011-05-04 |
| JP4453363B2 (ja) | 2010-04-21 |
| EP2317307A3 (en) | 2012-03-14 |
| JP2020073916A (ja) | 2020-05-14 |
| EP1475632A4 (en) | 2008-06-25 |
| EP1475632B1 (en) | 2013-05-22 |
| JP2010071995A (ja) | 2010-04-02 |
| US9274123B2 (en) | 2016-03-01 |
| US9658234B2 (en) | 2017-05-23 |
| EP1475632A1 (en) | 2004-11-10 |
| JP5842775B2 (ja) | 2016-01-13 |
| US7148069B2 (en) | 2006-12-12 |
| EP2317307B1 (en) | 2013-11-20 |
| US20160139134A1 (en) | 2016-05-19 |
| JP6699645B2 (ja) | 2020-05-27 |
| US20060286673A1 (en) | 2006-12-21 |
| JP2013015537A (ja) | 2013-01-24 |
| JP2018052972A (ja) | 2018-04-05 |
| AU2003211941A1 (en) | 2003-09-04 |
| CA2475011A1 (en) | 2003-08-21 |
| EP2336763A1 (en) | 2011-06-22 |
| US20050079624A1 (en) | 2005-04-14 |
| JP6278210B2 (ja) | 2018-02-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2475011C (en) | Method for analysis of compounds with amino group and analytical reagent therefor | |
| Petritis et al. | A comparative study of commercial liquid chromatographic detectors for the analysis of underivatized amino acids | |
| CN102510903B (zh) | 蛋白质和多肽的质谱鉴定和定量检测的方法学革新 | |
| JP5030586B2 (ja) | アミノ官能性化合物の分析方法及び装置 | |
| Lu et al. | Determination of non-protein cysteine in human serum by a designed BODIPY-based fluorescent probe | |
| Er et al. | Determination of seventeen free amino acids in human urine and plasma samples using quadruple isotope dilution mass spectrometry combined with hydrophilic interaction liquid chromatography–Tandem mass spectrometry | |
| US20110045598A1 (en) | Methods for determining enantiomeric purity with improved chiral selectors | |
| Gan et al. | Fluorescence quenching method for the determination of carbazochrome sodium sulfonate with aromatic amino acids | |
| Toyo'oka | Development of Benzofurazan− bearing Fluorescence Labeling Reagents for separation and detection in high− performance liquid chromatography | |
| KR101010899B1 (ko) | 발리올아민의 ｕｖ 분석방법 | |
| Bigelow et al. | Quantitative proteome mapping of nitrotyrosines | |
| You et al. | Application of 10‐ethyl‐acridine‐3‐sulfonyl chloride for HPLC determination of aliphatic amines in environmental water using fluorescence and APCI‐MS | |
| Lee et al. | The application of mass spectrometry in drug metabolism and pharmacokinetics | |
| JP2023548079A (ja) | 遊離チオール検出のための蛍光エルマンアッセイ | |
| JP6359365B2 (ja) | アミノ酸のアミノ基及びカルボキシル基を対象としたプレカラム誘導体化ｌｃ−ｍｓ分析法 | |
| Iwasaki et al. | Comparison of fluorescence reagents for simultaneous determination of hydroxylated phenylalanine and nitrated tyrosine by high‐performance liquid chromatography with fluorescence detection | |
| Ladouce et al. | Specific detection of protein carbonylation sites by 473 nm photodissociation mass spectrometry | |
| Gómez et al. | Probing protein surface with a solvent mimetic carbene coupled to detection by mass spectrometry | |
| Quanico et al. | On-tissue Direct Monitoring of Global Hydrogen/Deuterium Exchange by MALDI Mass Spectrometry: Tissue Deuterium Exchange Mass Spectrometry (TDXMS) | |
| Li et al. | A Rapid and Sensitive Method for Chiroptical Sensing of a-Amino Acids via Click-like Labeling with o-Phthaladehyde and p-Toluenethiol | |
| Seok et al. | Simultaneous determination of 14 underivatized amino acids using ion-pairing chromatography and isotope dilution tandem mass spectrometry for a reference measurement procedure | |
| Baig et al. | Analysis of amino acids by high performance liquid chromatography. | |
| GORNISCHEFF | Study of ionization efficiencies for derivatized compounds in LC/ESI/MS and their application for targeted analysis | |
| Popa‐Burke et al. | Assessing Compound Quality |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20230213 |