HILIC UPLC /QTof MS Giuseppe Paglia, 1 James Langridge, 2 and Giuseppe Astarita 3 Center for Systems Biology, University of Iceland, Iceland; 2-3. Wat
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1 HILIC UPLC /QTof MS Giuseppe Paglia, James Langridge, 2 and Giuseppe Astarita 3 Center for Systems Biology, University of Iceland, Iceland; 2-3. Waters Corporation, Manchester, UK and Milford, MA, USA UPLC HILIC Q-Tof DNA RNA. 6 ACQUITY UPLC ACQUITY UPLC BEH Amide SYNAPT G2 Progenesis. O HO OH NH 2. L HILIC UPLC QTof MS.
2 LC ACQUITY UPLC BEH Amide mm.7 µm A 0. % B 0. % 0.4 ml /min µl Partial loop with needle overfill ESI A% B% LC ACQUITY UPLC BEH Amid e mm.7 µm A 95 % 0 mm 5% ph 9 B 5 % 0 mm 95% ph 9 A% B% MS ESI PEEK /6 inch.6 mm O.D inch 0.27 mm I.D. 5 ft.5 m 450 mm WAT SYNAPT G2 Sensitivity.5 kv 30 V 5 V L / h 50 L / h 3 ng/l m/z m/z ml /min µl ESI Partial loop with needle overfill HILIC UPLC /QTof MS 2
3 LC /MS HILIC -MS,2 HILIC-UPLC/MS Reykjavik 0.5 ml 30 µl / 7 3 v/v ml 2 5 0,000 g 0.2 µm 0.3 ml / v/v 2 QC 5 QC Metabolites Molecular Formula MW [M+H] + [M-H] - Retention time (min) Concentration ng/l BASIC NEG POS Phenylalanine d 2 C 9 D 2 H 9 NO Succinate d 4 C 4 D 4 H 2 O Glucose 3 C 6 3 C 6 H 2 O Carnitine d 9 C 7 D 9 H 6 NO Glutamic Acid d 5 C 5 D 5 H 4 NO AMP 3 C 0, 5 N 5 3 C 0 H 4 5 N 5 O 7 P Octanoic Acid d 5 C 8 D 5 H O Lysine d 4 C 6 D 4 H 0 N 2 O UPLC/ MS 2 µm 80 A 50% B / v/v 50% 0.25 ml/min 30 A00% 0.25 ml/min % / v/v 5 HILIC UPLC /QTof MS 3
4 2 2 HILIC-UPLC camp 2. cgmp 3. dtmp 4. damp 5. UMP 6. dcmp 7. IMP 8. GMP 9. UDP Succinate 2. Panthotenate 3. 5-oxoproline 4. Malate 5. Dihydroorotic acid 6. Xanthine 7. Xanthosine 8. Folic Acid 9. Gluconate MTA 2. Phenylalanine 3. Carnitinen 4. Adenosine 5. Taurine 6. Citrulline 7. ADMA 8. Methyl-Histidine 9. Glutathione Ox 2. UPLC/MS HILIC UPLC /QTof MS 4
5 3A 3B ph 3C LC/MS HILIC 2 ES ES A 2 4. FAD 2. ADP-Glucose 3. ADP-Ribose 4. UDP-Glucose C B. AMP 2. ADP 3. ATP A B 50 mm HILIC 50 mm HSS T3 C 8 C HILIC UPLC /QTof MS 5
6 Class HMDB ID Metabolites Molecular Formula MW [M+H]+ [M-H]- Retention time (min) Suggested Condition Quantification Ions Internal Standard BASIC NEG POS Aminoacid HMDB00929 Tryptophan CH2N2O ACID POS Phenylalanine d2 2 Aminoacid HMDB0057 Arginine C6H4N4O ACID POS Lysine d4 3 Aminoacid HMDB00904 Citrulline C6H3N3O ACID POS Lysine d4 4 Aminoacid HMDB00574 Cysteine C3H7NO2S ACID POS Lysine d4 5 Aminoacid HMDB0077 Histidine C6H9N3O ACID POS Lysine d4 6 Aminoacid HMDB0082 Lysine C6H4N2O ACID POS Lysine d4 7 Aminoacid HMDB0059 Phenylalanine C9HNO ACID POS Phenylalanine d2 8 Aminoacid HMDB0062 Proline C5H9NO ACID POS Glutamic Acid d5 9 Aminoacid HMDB0072 Isoleucine C6H3NO ACID POS Phenylalanine d2 0 Aminoacid HMDB0068 Asparagine C4H8N2O ACID POS Phenylalanine d2 Aminoacid HMDB00725 Hydroxyproline C5H9NO ACID POS Glutamic Acid d5 2 Aminoacid HMDB00696 Methionine C5HNO2S ACID POS Phenylalanine d2 3 Aminoacid derivative HMDB745 Acetyl-methionine C7H3NO3S ACID POS Phenylalanine d2 4 Aminoacid derivative HMDB03337 Glutathione Oxidized C20H32N6O2S ACID POS Lysine d4 5 Aminoacid derivative HMDB0025 Glutathione Reduced C0H7N3O6S ACID POS Lysine d4 6 Aminoacid derivative HMDB00092 Dimethylglycine C4H9NO ACID POS Glutamic Acid d5 7 Aminoacid derivative HMDB0539 ADMA C8H8N4O ACID POS Lysine d4 8 Aminoacid derivative HMDB0092 Cystine C6H2N2O4S ACID POS Lysine d4 9 Aminoacid derivative HMDB0000 -Methylhistidine C7HN3O ACID POS Lysine d4 20 Aminoacid derivative HMDB00064 Creatine C4H9N3O ACID POS Phenylalanine d2 2 Biogenic Amine HMDB00259 Serotonin C0H2N2O ACID POS Phenylalanine d2 22 Biogenic Amine HMDB00068 Epinephrine C9H3NO ACID POS Phenylalanine d2 23 Carnitine HMDB0020 Acetylcarnitine C9H7NO ACID POS Carnitine d9 24 Carnitine HMDB00062 Carnitine C7H5NO ACID POS Carnitine d9 25 Carnitine HMDB00222 Palmitoylcarnitine C23H45NO ACID POS Carnitine d9 26 Nucleobase HMDB00262 T hymine C5H6N2O ACID POS Phenylalanine d2 27 Nucleobase HMDB00034 Adenine C5H5N ACID POS Phenylalanine d2 28 Nucleobase HMDB0032 Guanine C5H5N5O ACID POS Phenylalanine d2 29 Nucleobase HMDB0057 Hypoxanthine C5H4N4O ACID POS Phenylalanine d2 30 Nucleobase HMDB00300 Uracil C4H4N2O ACID POS Phenylalanine d2 3 Nucleoside HMDB00050 Adenosine C0H3N5O ACID POS Phenylalanine d2 32 Nucleoside HMDB00089 Cytidine C9H3N3O ACID POS Phenylalanine d2 33 Nucleoside derivative HMDB073 5-MTA CH5N5O3S ACID POS Phenylalanine d2 34 Nucleoside derivative HMDB00939 SAH C4H20N6O5S ACID POS Lysine d4 35 Nucleoside derivative HMDB4266 SAMe C5H22N6O5S ACID POS Lysine d4 36 Nucleoside derivative HMDB057 AICAR C9H4N4O ACID POS Phenylalanine d2 37 Phosphorilated compound HMDB0565 Phosphorylcholine C5H4NO4P Nd 5. ACID POS AMP 3C0, 5N5 38 Sugar HMDB00660 Fructose C6H2O ACID POS * Glucose 3C6 39 Sugar HMDB054 Glucosamine C6H3NO ACID POS Glucose 3C6 40 Sugar HMDB0022 Glucose C6H2O ACID POS * Glucose 3C6 4 Sugar HMDB4627 Lactose C2H22O ACID POS * Glucose 3C6 42 Sugar HMDB00765 Mannitol C6H4O ACID POS * Glucose 3C6 43 Sugar HMDB0069 Mannose C6H2O ACID POS * Glucose 3C6 44 Sugar HMDB0025 Acetyl-Glucosamine C8H5NO ACID POS Glucose 3C6 45 Sugar HMDB00258 Sucrose C2H22O ACID POS * Glucose 3C6 46 Sugar HMDB0323 Raffinose C8H32O ACID POS * Glucose 3C6 47 Vitamin HMDB002 Folic acid C9H9N7O ACID POS Phenylalanine d2 48 Vitamin HMDB Me-THF C20H25N7O ACID POS Glutamic Acid d5 49 Vitamin HMDB0406 Niacinamide C6H6N2O ACID POS Carnitine d9 50 Vitamin HMDB0488 Nicotinic acid C6H5NO ACID POS Carnitine d9 5 Vitamin HMDB0392 PABA C7H7NO ACID POS Carnitine d9 52 Vitamin HMDB00607 Vitamin B2 C63H88CoN4O4P ACID POS ** Glutamic Acid d5 53 Vitamin HMDB00030 Biotin C0H6N2O3S ACID POS Carnitine d9 54 Vitamin HMDB00244 Riboflavin C7H20N4O ACID POS Phenylalanine d2 55 Vitamin HMDB00239 Pyridoxine C8HNO ACID POS Phenylalanine d2 56 Vitamin HMDB00235 Thiamine C2H6N4OS ACID POS Lysine d4 57 Vitamin HMDB00097 Choline C5H4NO ACID POS Carnitine d9 58 Aminoacid HMDB009 Aspartic Acid C4H7NO ACID NEG Glutamic Acid d5 59 Aminoacid HMDB0064 Glutamine C5H0N2O ACID NEG Glutamic Acid d5 60 Aminoacid HMDB0087 Serine C3H7NO ACID NEG Glutamic Acid d5 6 Aminoacid HMDB0067 Threonine C4H9NO ACID NEG 8.05 Glutamic Acid d5 62 Aminoacid HMDB006 Alanine C3H7NO ACID NEG Glutamic Acid d5 63 Aminoacid HMDB0058 Tyrosine C9HNO ACID NEG Phenylalanine d2 64 Aminoacid HMDB00883 Valine C5HNO ACID NEG 6.07 Phenylalanine d2 65 Aminoacid derivative HMDB Oxoproline C5H7NO ACID NEG Succinate d4 66 Nucleobase HMDB00292 Xanthine C5H4N4O ACID NEG Phenylalanine d2 67 Nucleobase HMDB00289 Uric acid C5H4N4O ACID NEG Phenylalanine d2 68 Nucleobase HMDB00296 Uridine C9H2N2O ACID NEG Phenylalanine d2 69 Nucleoside HMDB00299 Xanthosine C0H2N4O ACID NEG Phenylalanine d2 70 Nucleoside HMDB0033 Guanosine C0H3N5O ACID NEG Phenylalanine d2 7 Nucleoside HMDB0095 Inosine C0H2N4O ACID NEG Phenylalanine d2 72 Organic Acid HMDB00072 Aconitic Acid C6H6O ACID NEG Succinate d4 73 Organic Acid HMDB03349 Dihydroorotic Acid C5H6N2O ACID NEG Succinate d4 74 Organic Acid HMDB0039 Glyceric Acid C3H6O ACID NEG Succinate d4 75 Organic Acid HMDB0056 Malic Acid C4H6O ACID NEG Succinate d4 76 Organic Acid HMDB0034 Fumaric Acid C4H4O ACID NEG Succinate d4 77 Organic Acid HMDB00094 Citric Acid C6H8O ACID NEG 9.09 Phenylalanine d2 78 Organic Acid HMDB00227 Mevalonic Acid C6H2O ACID NEG Succinate d4 79 Organic Acid HMDB00226 Orotic Acid C5H4N2O ACID NEG Succinate d4 80 Organic Acid HMDB0895 Salicylic Acid C7H6O ACID NEG Octanoic Acid d5 8 Organic Acid HMDB00254 Succinic Acid C4H6O ACID NEG 7.09 Succinate d4 82 Sugar HMDB00625 Gluconic Acid C6H2O ACID NEG Glucose 3C6 83 Sugar HMDB0027 Glucuronic Acid C6H0O ACID NEG Glutamic Acid d5 84 Vitamin HMDB0007 Pyridoxic Acid C8H9NO ACID NEG Succinate d4 85 Vitamin HMDB00044 Ascorbic Acid C6H8O ACID NEG Succinate d4 86 Vitamin Panthotenic Acid C9H7NO ACID NEG Succinate d4 87 Aminoacid HMDB0048 Glutamic Acid C5H9NO BASIC NEG Glutamic Acid d5 88 Aminoacid derivative HMDB00766 Acetylalanine C5H9NO BASIC NEG Phenylalanine d2 89 Aminoacid derivative HMDB0025 Taurine C2H7NO3S BASIC NEG Glutamic Acid d5 90 Coenzyme HMDB0423 CoA C2H36N7O6P3S BASIC NEG AMP 3C0, 5N5 9 Coenzyme HMDB00902 NAD C2H27N7O4P BASIC NEG AMP 3C0, 5N5 92 Coenzyme HMDB0027 NADP C2H28N7O7P BASIC NEG AMP 3C0, 5N5 93 Coenzyme HMDB0248 FAD C27H33N9O5P BASIC NEG AMP 3C0, 5N5 94 dnucleotide HMDB00058 camp C0H2N5O6P BASIC NEG AMP 3C0, 5N5 95 dnucleotide HMDB034 cgmp C0H2N5O7P BASIC NEG AMP 3C0, 5N5 96 dnucleotide HMDB00905 damp C0H4N5O6P BASIC NEG AMP 3C0, 5N5 97 dnucleotide HMDB0202 dcmp C9H4N3O7P BASIC NEG AMP 3C0, 5N5 98 dnucleotide HMDB0227 dtmp C0H5N2O8P BASIC NEG AMP 3C0, 5N5 99 Nucleoside derivative HMDB00536 Adenylosuccinic Acid C4H8N5OP BASIC NEG Glutamic Acid d5 00 Nucleoside diphosphate HMDB00295 UDP C9H4N2O2P BASIC NEG AMP 3C0, 5N5 0 Nucleoside dip derivative HMDB06557 ADP-Glucose C6H25N5O5P BASIC NEG AMP 3C0, 5N5 02 Nucleoside dip derivative HMDB078 ADP-Ribose C5H23N5O4P BASIC NEG AMP 3C0, 5N5 03 Nucleoside dip derivative HMDB00286 UDP-Glucose C5H24N2O7P BASIC NEG AMP 3C0, 5N5 04 Nucleoside diphsphate HMDB034 ADP C0H5N5O0P BASIC NEG AMP 3C0, 5N5 05 Nucleoside diphsphate HMDB020 GDP C0H5N5OP BASIC NEG AMP 3C0, 5N5 06 Nucleoside Triphosphate HMDB0273 GTP C0H6N5O4P BASIC NEG AMP 3C0, 5N5 07 Nucleoside Triphosphate HMDB00538 AT P C0H6N5O3P BASIC NEG AMP 3C0, 5N5 08 Nucleotide HMDB00045 AMP C0H4N5O7P BASIC NEG AMP 3C0, 5N5 09 Nucleotide HMDB00095 CMP C9H4N3O8P BASIC NEG AMP 3C0, 5N5 0 Nucleotide HMDB0397 GMP C0H4N5O8P BASIC NEG AMP 3C0, 5N5 Nucleotide HMDB0075 IMP C0H3N4O8P BASIC NEG AMP 3C0, 5N5 2 Nucleotide HMDB00288 UMP C9H3N2O9P BASIC NEG AMP 3C0, 5N5 3 Organic Acid HMDB Hydroxybutyric Acid C4H8O BASIC NEG Phenylalanine d2 4 Organic Acid - 4-Methyl-2-Oxopentanoic Acid C6H0O BASIC NEG Octanoic Acid d5 5 Organic Acid HMDB0090 Lactic acid C3H6O BASIC NEG Succinate d4 6 Phosphorilated compound HMDB Phosphoglyceric Acid C3H7O7P BASIC NEG AMP 3C0, 5N5 7 Phosphorilated compound - Glycerol Monophosphate C3H9O6P BASIC NEG AMP 3C0, 5N5 8 Phosphorilated compound HMDB05 Phosphocreatine C4H0N3O5P BASIC NEG AMP 3C0, 5N5 9 Phosphorilated compound HMDB00263 Phosphoenolpyruvic Acid C3H5O6P BASIC NEG AMP 3C0, 5N5 20 Phosphorilated Sugar HMDB036 6-Phosphogluconic Acid C6H3O0P BASIC NEG AMP 3C0, 5N5 2 Phosphorilated Sugar HMDB0024 Fructose 6-Phosphate C6H3O9P BASIC NEG AMP 3C0, 5N5 22 Phosphorilated sugar HMDB0058 Fructose-,6-Diphosphate C6H4O2P BASIC NEG AMP 3C0, 5N5 23 Phosphorilated Sugar HMDB0254 Glucosamine-6-Phosphate C6H4NO8P BASIC NEG AMP 3C0, 5N5 24 Phosphorilated Sugar HMDB040 Glucose 6-Phosphate C6H3O9P BASIC NEG AMP 3C0, 5N5 25 Phosphorilated Sugar HMDB0548 Ribose 5-Phosphate C5HO8P BASIC NEG AMP 3C0, 5N5 * [M+Na]+ ** [M+2H]2+ 2. HILIC UPLC /QTof MS 6
7 4 R LOD 00 ng/ml 4. HILIC UPLC /QTof MS 7
8 HILIC-UPLC/MS 5 m/z 50 m/z 000 Progenesis MS HILIC UPLC /QTof MS 8
9 6A 6B 2 A Arginine ES + B Fructose-6-P ES - Glucose-6-P SAH GMP UMP Carnitine Inosine 5-MTA IMP Hypoxanthine Fragment Inosine Fragment IMP AMP 6. ESI A ESI B UPLC/MS HILIC UPLC /QTof MS 9
10 HILIC UPLC/TOF-MS References. Paglia G, Magnusdottir M, Thorlacius S, Sigurjonsson OE, Guethmundsson S, Palsson BO, Thiele I. Intracellular metabolite profiling of platelets: evaluation of extraction processes and chromatographic strategies. J Chromatogr B Analyt Technol Biomed Life Sci. 202; 898:-20. doi:0.06/j. jchromb Paglia G, Hrafnsdottir S, Magnusdottir M, Fleming RM, Thorlacius S, Palsson BO, Thiele I. Monitoring metabolites consumption and secretion in cultured cells using ultra-performance liquid chromatography quadrupole-time of flight mass spectrometry (UPLC-Q-ToF-MS). Anal Bioanal Chem. 202;402(3): doi:0.007/s TEL FAX F TEL FAX Waters ACQUITY UPLC SYNAPT Progenesis UPLC The Science of What s Possible Waters Corporation Q-Tof Waters Corporation 204 Waters Corporation. Printed in Japan JA PDF
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Hydrocortisone Sodium Phosphate 3.5 1.0 0.5 1 μg/ml 3.0 2.5 25 ng/ml 0.0 0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 min 0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 min Fig.1 Chromatograms of Hydrocortisone
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2,2-2,2 -Iminodiethanol Diethanol amine CAS 111-42-2 C 4 H 11 NO 2 105.1356-105.0790-28 C 1) 1.0881 g/cm 3 1)
平成26年度 化学物質分析法開発報告書
2,2-2,2 -Iminodiethanol Diethanol amine CAS 111-42-2 C 4 H 11 NO 2 105.1356-105.0790-28 C 1) 1.0881 g/cm 3 1)
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3--2-3-Iodo-2-propynyl butylcarbamate (IPBC) Carbamic acid, butyl-, 3-iodo-2-propynyl ester Iodocarb CAS 55406-53-6 C 8 H 12 NO 2 I C (g/cm 3 ) (mmhg) log P ow 281.09 (280.9910) 64 68 1.51 1.57 (20 C)
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2016 年 10 月 19 日 ( 水 ) バイオ情報解析演習 ウェブツールを活用した生物情報解析 (1) 配列と代謝経路の解析の基礎 有用物質生産菌を合理的に作ろう! 設計 試作 ベンチテスト 完成 プラスミド 効率的な代謝経路を設計する 文献調査代謝パスウェイの探索代謝シミュレーション 実際に微生物に組み込む データベースから有用遺伝子を探索する遺伝子組換え技術 培養をして問題点を突き止める
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N,N- N,N-Dimethylacetamide Acethyldimethylamine CAS 127-19-5 C 4 H 9 NO 87.12 ~ 87.14 87.68413 163-165 C 1) - 18.59 C 2) 1 mg/l 25 C 3) 3.3 hpa 2 C 4) log P ow -.77 2).9429 2/4 C 1) 3.1 4) 1.31E - 8 atm-m
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生化学への導入 平成 30 年 4 月 12 日 病態生化学分野教授 ( 生化学 2) 山縣和也 生化学とは 細胞の化学的構成成分 およびそれらが示す化学反応と代謝機序を取り扱う学問 ハーパー生化学 生化学 1 生化学 2 生化学 炭水化物 / 糖 脂質 アミノ酸について勉強します 糖 脂質生化学 2 脂質 アミノ酸 核酸 生化学 1 生化学と医学は密接に関係する 炭水化物 脂質 生化学 蛋白質 核酸
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