CA2460131C - Mass labels - Google Patents
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- Publication number
- CA2460131C CA2460131C CA002460131A CA2460131A CA2460131C CA 2460131 C CA2460131 C CA 2460131C CA 002460131 A CA002460131 A CA 002460131A CA 2460131 A CA2460131 A CA 2460131A CA 2460131 C CA2460131 C CA 2460131C
- Authority
- CA
- Canada
- Prior art keywords
- mass
- labels
- label
- moiety
- peptide
- 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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- 150000001413 amino acids Chemical class 0.000 claims abstract description 66
- 239000003550 marker Substances 0.000 claims abstract description 49
- 238000010606 normalization Methods 0.000 claims abstract description 28
- 150000002500 ions Chemical class 0.000 claims description 161
- 238000000034 method Methods 0.000 claims description 132
- 239000000523 sample Substances 0.000 claims description 103
- 108090000623 proteins and genes Proteins 0.000 claims description 93
- 102000004169 proteins and genes Human genes 0.000 claims description 91
- 235000018102 proteins Nutrition 0.000 claims description 84
- 238000004458 analytical method Methods 0.000 claims description 79
- 238000006062 fragmentation reaction Methods 0.000 claims description 73
- 238000013467 fragmentation Methods 0.000 claims description 71
- 235000001014 amino acid Nutrition 0.000 claims description 70
- 238000004949 mass spectrometry Methods 0.000 claims description 54
- 238000001360 collision-induced dissociation Methods 0.000 claims description 53
- 239000012491 analyte Substances 0.000 claims description 36
- 239000003446 ligand Substances 0.000 claims description 36
- 230000035945 sensitivity Effects 0.000 claims description 33
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 26
- 230000002708 enhancing effect Effects 0.000 claims description 20
- 229960002685 biotin Drugs 0.000 claims description 16
- 239000011616 biotin Substances 0.000 claims description 16
- 235000020958 biotin Nutrition 0.000 claims description 15
- 108020004707 nucleic acids Proteins 0.000 claims description 15
- 102000039446 nucleic acids Human genes 0.000 claims description 15
- 150000007523 nucleic acids Chemical class 0.000 claims description 15
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 14
- 238000001514 detection method Methods 0.000 claims description 13
- 238000000926 separation method Methods 0.000 claims description 13
- 108091034117 Oligonucleotide Proteins 0.000 claims description 12
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 8
- 235000003704 aspartic acid Nutrition 0.000 claims description 6
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 238000010195 expression analysis Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 238000001962 electrophoresis Methods 0.000 claims description 4
- 230000000155 isotopic effect Effects 0.000 claims description 4
- 238000012512 characterization method Methods 0.000 claims description 3
- 238000010494 dissociation reaction Methods 0.000 claims description 3
- 230000005593 dissociations Effects 0.000 claims description 3
- 238000009396 hybridization Methods 0.000 claims description 3
- 238000012163 sequencing technique Methods 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 238000011223 gene expression profiling Methods 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 346
- 102000004196 processed proteins & peptides Human genes 0.000 description 186
- 239000012634 fragment Substances 0.000 description 75
- 229940024606 amino acid Drugs 0.000 description 65
- 238000012034 trail making test Methods 0.000 description 65
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
- 238000001228 spectrum Methods 0.000 description 47
- 238000002372 labelling Methods 0.000 description 41
- 125000005647 linker group Chemical group 0.000 description 32
- 230000007017 scission Effects 0.000 description 31
- 238000003776 cleavage reaction Methods 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 27
- 239000003153 chemical reaction reagent Substances 0.000 description 27
- 125000003277 amino group Chemical group 0.000 description 26
- 239000000243 solution Substances 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 26
- 150000001720 carbohydrates Chemical class 0.000 description 23
- 235000014633 carbohydrates Nutrition 0.000 description 22
- 238000001819 mass spectrum Methods 0.000 description 21
- 239000011347 resin Substances 0.000 description 21
- 229920005989 resin Polymers 0.000 description 21
- 238000004885 tandem mass spectrometry Methods 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 229930182817 methionine Natural products 0.000 description 19
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 18
- 150000001408 amides Chemical class 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 239000004472 Lysine Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- 150000003573 thiols Chemical class 0.000 description 16
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 230000005588 protonation Effects 0.000 description 15
- 241000894007 species Species 0.000 description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
- 238000010647 peptide synthesis reaction Methods 0.000 description 14
- 229920001184 polypeptide Polymers 0.000 description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 13
- 239000007789 gas Substances 0.000 description 13
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 13
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 12
- 230000007246 mechanism Effects 0.000 description 12
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 238000002474 experimental method Methods 0.000 description 11
- 230000014509 gene expression Effects 0.000 description 11
- 238000005040 ion trap Methods 0.000 description 11
- 125000006239 protecting group Chemical group 0.000 description 11
- -1 2-nitrobenzyl esters Chemical class 0.000 description 10
- 235000004279 alanine Nutrition 0.000 description 10
- 238000003491 array Methods 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 238000002955 isolation Methods 0.000 description 10
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 10
- 108010016626 Dipeptides Proteins 0.000 description 9
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000013459 approach Methods 0.000 description 9
- 229940077731 carbohydrate nutrients Drugs 0.000 description 9
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- 230000004048 modification Effects 0.000 description 9
- 238000012986 modification Methods 0.000 description 9
- 235000000346 sugar Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 8
- 101710118538 Protease Proteins 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 8
- 238000002101 electrospray ionisation tandem mass spectrometry Methods 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- 108091005981 phosphorylated proteins Proteins 0.000 description 8
- BZQFBWGGLXLEPQ-REOHCLBHSA-N phosphoserine Chemical compound OC(=O)[C@@H](N)COP(O)(O)=O BZQFBWGGLXLEPQ-REOHCLBHSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 7
- 108090001008 Avidin Proteins 0.000 description 7
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 7
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 7
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 7
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 7
- 239000004473 Threonine Substances 0.000 description 7
- 238000013375 chromatographic separation Methods 0.000 description 7
- 235000018417 cysteine Nutrition 0.000 description 7
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000010265 fast atom bombardment Methods 0.000 description 7
- 239000011159 matrix material Substances 0.000 description 7
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 7
- 239000007790 solid phase Substances 0.000 description 7
- DLZKEQQWXODGGZ-KCJUWKMLSA-N 2-[[(2r)-2-[[(2s)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)[C@@H](C)NC(=O)[C@@H](N)CC1=CC=C(O)C=C1 DLZKEQQWXODGGZ-KCJUWKMLSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- BZQFBWGGLXLEPQ-UHFFFAOYSA-N O-phosphoryl-L-serine Natural products OC(=O)C(N)COP(O)(O)=O BZQFBWGGLXLEPQ-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 108090000631 Trypsin Proteins 0.000 description 6
- 102000004142 Trypsin Human genes 0.000 description 6
- 238000001042 affinity chromatography Methods 0.000 description 6
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 6
- 210000004899 c-terminal region Anatomy 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000010511 deprotection reaction Methods 0.000 description 6
- 229950006137 dexfosfoserine Drugs 0.000 description 6
- 230000005684 electric field Effects 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 108091005601 modified peptides Proteins 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical group OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 150000008163 sugars Chemical class 0.000 description 6
- 239000012588 trypsin Substances 0.000 description 6
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 5
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- UQBOJOOOTLPNST-UHFFFAOYSA-N Dehydroalanine Chemical compound NC(=C)C(O)=O UQBOJOOOTLPNST-UHFFFAOYSA-N 0.000 description 5
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 5
- 108010001441 Phosphopeptides Proteins 0.000 description 5
- 206010070834 Sensitisation Diseases 0.000 description 5
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 5
- 150000008378 aryl ethers Chemical class 0.000 description 5
- 230000027455 binding Effects 0.000 description 5
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 229940093499 ethyl acetate Drugs 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
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- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 5
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 5
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000011987 methylation Effects 0.000 description 5
- 238000007069 methylation reaction Methods 0.000 description 5
- FLEYLGCAQDCGHN-UHFFFAOYSA-N n-methyl-α-β-dehydroalanine Chemical group CNC(=C)C(O)=O FLEYLGCAQDCGHN-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000000269 nucleophilic effect Effects 0.000 description 5
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 5
- 230000026731 phosphorylation Effects 0.000 description 5
- 238000006366 phosphorylation reaction Methods 0.000 description 5
- USRGIUJOYOXOQJ-GBXIJSLDSA-N phosphothreonine Chemical compound OP(=O)(O)O[C@H](C)[C@H](N)C(O)=O USRGIUJOYOXOQJ-GBXIJSLDSA-N 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 230000000717 retained effect Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 4
- 102000004856 Lectins Human genes 0.000 description 4
- 108090001090 Lectins Proteins 0.000 description 4
- 101001018085 Lysobacter enzymogenes Lysyl endopeptidase Proteins 0.000 description 4
- 125000001429 N-terminal alpha-amino-acid group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000000539 amino acid group Chemical group 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000001212 derivatisation Methods 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 235000013922 glutamic acid Nutrition 0.000 description 4
- 239000004220 glutamic acid Substances 0.000 description 4
- 239000002523 lectin Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 4
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 4
- DCWXELXMIBXGTH-UHFFFAOYSA-N phosphotyrosine Chemical compound OC(=O)C(N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-UHFFFAOYSA-N 0.000 description 4
- 238000011002 quantification Methods 0.000 description 4
- 238000012552 review Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical group O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 102100031680 Beta-catenin-interacting protein 1 Human genes 0.000 description 3
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 3
- 101800001415 Bri23 peptide Proteins 0.000 description 3
- 125000001433 C-terminal amino-acid group Chemical group 0.000 description 3
- 102400000107 C-terminal peptide Human genes 0.000 description 3
- 101800000655 C-terminal peptide Proteins 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 101000993469 Homo sapiens Beta-catenin-interacting protein 1 Proteins 0.000 description 3
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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
- G01N33/68—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
- 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
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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
- G01N33/6851—Methods of protein analysis involving laser desorption ionisation mass spectrometry
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J49/00—Particle spectrometers or separator tubes
- H01J49/02—Details
- H01J49/04—Arrangements for introducing or extracting samples to be analysed, e.g. vacuum locks; Arrangements for external adjustment of electron- or ion-optical components
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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
Landscapes
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
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- Urology & Nephrology (AREA)
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- Spectroscopy & Molecular Physics (AREA)
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- Biophysics (AREA)
- Optics & Photonics (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01307830 | 2001-09-14 | ||
| EP01307830.8 | 2001-09-14 | ||
| PCT/GB2002/004240 WO2003025576A2 (en) | 2001-09-14 | 2002-09-16 | Mass labels |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2460131A1 CA2460131A1 (en) | 2003-03-27 |
| CA2460131C true CA2460131C (en) | 2006-11-21 |
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| CA (1) | CA2460131C (enExample) |
| DE (1) | DE60223696T2 (enExample) |
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| ES (1) | ES2296996T3 (enExample) |
| PT (1) | PT1425586E (enExample) |
| WO (1) | WO2003025576A2 (enExample) |
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2002
- 2002-09-16 DE DE60223696T patent/DE60223696T2/de not_active Expired - Lifetime
- 2002-09-16 DK DK02767650T patent/DK1425586T3/da active
- 2002-09-16 ES ES02767650T patent/ES2296996T3/es not_active Expired - Lifetime
- 2002-09-16 EP EP02767650A patent/EP1425586B1/en not_active Expired - Lifetime
- 2002-09-16 PT PT02767650T patent/PT1425586E/pt unknown
- 2002-09-16 CA CA002460131A patent/CA2460131C/en not_active Expired - Lifetime
- 2002-09-16 WO PCT/GB2002/004240 patent/WO2003025576A2/en not_active Ceased
- 2002-09-16 JP JP2003529154A patent/JP4290003B2/ja not_active Expired - Lifetime
- 2002-09-16 US US10/489,341 patent/US7732378B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| PT1425586E (pt) | 2007-12-31 |
| WO2003025576A3 (en) | 2003-07-31 |
| JP4290003B2 (ja) | 2009-07-01 |
| DK1425586T3 (da) | 2008-02-11 |
| EP1425586A2 (en) | 2004-06-09 |
| JP2005503557A (ja) | 2005-02-03 |
| DE60223696T2 (de) | 2009-01-29 |
| ES2296996T3 (es) | 2008-05-01 |
| US7732378B2 (en) | 2010-06-08 |
| DE60223696D1 (de) | 2008-01-03 |
| EP1425586B1 (en) | 2007-11-21 |
| CA2460131A1 (en) | 2003-03-27 |
| WO2003025576A2 (en) | 2003-03-27 |
| US20050048489A1 (en) | 2005-03-03 |
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