A new concept for isotope ratio monitoring LC/MS. A Wide Range of Applications

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1 A new concept for isotope ratio monitoring LC/MS A Wide Range of Applications Andreas Hilkert, Dieter Juchelka, Michael Krummen Thermo Electron (Bremen) GmbH

2 Overview Introduction in Isotope Ratio Monitoring-LC/MS (irm-lc/ms) Technology Operating Modes New Applications by irm-lc/ms Authenticity Control Detection of adulteration by sugars in honey. Determination of Origin Differentiation of analgesic drugs. Molecular Biology Carbon isotopic characterization of rrna. Biogeochemistry Plant metabolism study of organic acids. Forensic Chemistry Analysis of aspartic acid in cadaver blood samples.

3 Why irm LC/MS? δ 13 C analysis of individual compounds with: High molecular weight High polarity Thermal instability Low vapour pressure Less sample preparation No derivatization No isotope dilution Less risk of fractionation

4 Comparison between irm GC/MS and irm LC/MS irm GC/MS GC Elution of separated compounds Combustion Reactor He Gas Dryer He + H 2 O CO 2 CO 2 CO 2 Open Split Isotope Ratio MS Helium as carrier for Separation of compounds Transfer to the IRMS Helium has No impact on combustion No effects in the IRMS Dry combustion (oxidation) in the He phase

5 Comparison between irm GC/MS and irm LC/MS irm LC/MS (first strategy) HPLC Separation of the mobile Phase Combustion Reactor Gas Dryer He He + H 2 O CO 2 CO 2 CO 2 Open Split Isotope Ratio MS Solvents as carrier for Separation of compounds Solvents are Oxidized Hazardous to IRMS No solvents to reactor or IRMS First approaches ( 91, 93) Moving Wire Drying system (difficult to use) Particle Beam Separation (low sensitivity, fractionation)

6 A New Strategy HPLC Separation of the mobile Phase Combustion Reactor Gas Dryer He He + H 2 O CO 2 CO 2 CO 2 Open Split Isotope Ratio MS HPLC Gas Dryer CO 2 CO 2 CO 2 IRMS Oxidation Reactor Separation He of the mobile Phase He + H 2 O Open Split

7 Scheme of the LC IsoLink Interface HPLC Oxidation Reagent Needle Port 6-Port- Valve Two-Head Pumps T-Piece Isotope Ratio MS Acid/Catalyst T = 99.9 C Oxidation Reactor He + CO 2 Gas Dryer Open Split CO2 Separation Unit He He + CO + H O 2 2 He He + H O 2 Waste (mobile phase)

8 HPLC Resolution m/z 44 (mv) HPLC separation of carbohydrates Sucrose Glucose Galactose Fructose Mannitol Sorbitol Time (s) HPLC resolution is maintained Parameters: HPLC flow: 300 µl/min Oxidation reagent: 60 µl/min (NH 4 ) 2 S 2 O 8, 100g/l Column: 700 CH Carbohydrate Column, 90 C Reactor: 99.9 C CO 2 Exchanger: 1 ml/min He flow

9 Authenticity Control of Honey Investigation of the adulteration of honey analyzing glucose, sucrose, fructose Mass 44 (mv) Glucose Fructose Honey Glucose Fructose Area δ 13 C δ 13 C Fru/Glu A pure 8000 B C adulterated pure Sucrose D E adulterated adulterated Time (s) Absolute δ 13 C value δ 13 C difference, Glu Fru Ratio of area, Fru / Glu

10 Source Differentiation of Drugs Determination of different analgesic compounds. δ 13 C of Paracetamol (Acetamidophenol) and Aspirin (Acetylsalicylic Acid; ASA). Mass 44 (mv) Reference gas pulses H =O C N CH 3 OH Paracetamol (Acetamidophenol) O OH C O = Aspirin (Acetylsalicylic Acid) =O C CH 3 δ 13 C ( ) Tablet Type Paracetamol ASA µ-ea A Country A Country B C D E F D G Time (s) Tablet type A has the same origin 4 sources of ASA Producer D use different ASA sources

11 µ-ea Direct Injecton Fast analysis of all water soluble compounds HPLC Analysis µ-ea m/z 44 (mv) Reference gas pulses Additive unknown, Additive unknown, Paracetamol, Additive unknown, Direct Loop Injection, Time (s) Analysis of a tablet followed by direct loop injection (µ-ea). Loop size of the HPLC injector was 5 ul, the loop size of the µ-ea injector was 10 ul, which results in two-fold response of the µ-ea peak

12 µ-ea Reproducibility Bulk Injection of Amphetamine m/z 44 (mv) Reference Gas CH 3 NH 2 Amount Sample Amphetamine Carbon δ 13 C S.D. n (ng) (ng) ( ) ( ) # Mean Time (s) e.g., 5 x bulk injections of 218 ng amphetamine Reliable reproducibility of the δ 13 C values # # #

13 irm-lc/ms of NaOH-hydrolyzed E. coli RNA Linkage of microbiological species identity with carbon source utilization by carbon isotopic characterization of rrna. Cell growth and Isolation: RNA was extracted from overnight cultures of E. coli grown on M9 minimal salts with glucose as sole carbon source Medium. A: Adenosine Nucleotides Hydrolyse: 0.2 N NaOH for 15 min at 50 C

14 Carbon Isotopic Composition of Individual Peaks from NaOH-hydrolyzed E. coli RNA *Peaks are numbered from first- to last-eluting The carbon isotopic composition of RNA closely reflects that of the growth substrate. A: Adenosine Nucleotides

15 δ 13 C Analysis of Fruit Juice Organic Acids m/z 44 (mv) Reference Gas Pulses Tartaric Acid Quinic Acid Malic Acid Benzoic Acid Citric Acid HPLC Column: Allure Organic Acids, 300 mm x 4.6 mm, 5 µm Flow: 500 µl/min Mobile Phase: 100 mm KH 2 PO 4, ph Time (s)

16 δ 13 C Analysis of Organic Acids δ 13 C= ± 0.34 Citric Acid δ 13 C= ± 0.11 δ 13 C ( ) δ 13 C= ± 0.22 Malic Acid δ 13 C= ± 0.15 δ 13 C= ± 0.35 Quinic Acid δ 13 C= ± δ 13 C= ± 0.32 Tartaric Acid δ 13 C= ± relates to 64 ng of carbon (tartaric acid) Amount (ng)

17 irm-lc/ms: δ 13 C Analysis of an Extract of Geranium pratense (May 2004) Plant metabolism study of organic acids m/z Malic Acid δ 13 C= std. dev.= 0.05 n=3 Amplitude Citric Acid δ 13 C= std. dev.= 0.10 n= Time (s)

18 Analysis of Volatile Fatty Acids by irm-lc/ms 1. Formate 2. Lactate 3. Acetate 4. Propionate Pump 1: 200 mg/l (NH 4 ) 2 S 2 O 8, 50µl/min Pump 2: 2M H 3 PO 4, no AgNO 3 -catalyst, 50µl/min Reactor: 99.9 C Data: Prof. Hinrichs Univ. Bremen

19 Linearity of the IRMS - Signal Amounts injected : 8.8 nmol 0.28 nmol Formate EA δ 13 C: (SD = 0.05) Lactate EA δ 13 C: (SD = 0.03) d13c (per mil) d13c (per mil) Mean δ 13 C: (SD = 0.6) Mean δ 13 C: (SD = 0.4) Concentration (µmol/l) Concentration (µmol/l) Acetate Mean δ 13 C: (SD = 1.3) Propionate d13c (per mil) EA δ 13 C: (SD = 0.1) d13c (per mil) EA δ 13 C: (SD = 0.1) Mean δ 13 C: (SD = 0.8) Data: Prof. Hinrichs Univ. Bremen Concentration (µmol/l) Concentration (µmol/l)

20 δ 13 C Analysis of Aspartic Acid in Cadaver Blood HO O NH 2 OH Aspartic Acid O Aspartic Acid Peak δ 13 C ( ) Sample δ 13 C ( ) Std. Dev. A B C m/z 44 (mv) D E F Time (s) Standard G H Mobile Phase: 10mM NaH 2 PO 4 *H 2 O, ph 4.7, Flow: 300 µl/min HPLC Column: Nova-Pack C18, 60 Å (4 µm, 3.9 mm x 300 mm).

21 Summary irm-lc/ms opens a wide range of interesting applications. Macromolecules, non-volatile components and components which tend to decompose are directly accessible for precise isotopic analysis.

22 Acknowledgements Barbara J. MacGregor and Adam Friedman, Department of Marine Sciences, University of North Carolina, Chapel Hill, N.C. Elena Hettmann and Gerd Gleixner, Max-Planck-Institut für Biogeochemie, Jena Jean-Philippe Godin and Jörg Hau, Nestlé Research Center, Lausanne Kurt-Peter Raezke, APPLICA GmbH, Bremen

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