Fundamentals and systematics of the non-statistical distributions of isotopes in natural compounds

Naturwissenschaften

Volumn 90, Issue 12, 2003, Pages 537-552

  Schmidt, Hanns Ludwig ^a,b  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b NONE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; ISOTOPE; NATURAL PRODUCT; NITROGEN; OXYGEN; SULFUR;

ISOTOPE;

CHEMICAL REACTION KINETICS; CHEMOTAXONOMY; COMPUTER PREDICTION; IN VIVO STUDY; METABOLIC ACTIVATION; METABOLITE; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; NON STATISTICAL DISTRIBUTION; RADIOISOTOPE DISTRIBUTION; REVIEW; STATISTICAL ANALYSIS; STEADY STATE; THERMODYNAMICS;

BIOLOGICAL FACTORS; BIOMETRY; ISOTOPES; KINETICS;

EID: 0346786497     PISSN: 00281042     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00114-003-0485-5     Document Type: Review

References (83)

1. Arnelle DR, O'Leary MH (1992) Binding of carbon dioxide to phosphoenolpyruvate carboxykinase deduced from kinetic isotope effects. Biochemistry 31:4363-4368
2. Balabane M, Galimov E, Hermann M, Letolle R (1987) Hydrogen and carbon isotope fractionation during experimental production of bacterial methane. Org Geochem 11:115-119
3. Beaumont VI, Jahnke LL, Des Marais DJ (2000) Nitrogen isotopic fractionation in the synthesis of photosynthetic pigments in Rhodobacter capsulatus and Anabaena cylindrica. Org Geochem 31:1075-1085
4. Blanco D, Morán MJ, Gutiérrez MD, Moreno J, Dapena E, Mangas J (1992) Biochemical study of the ripening of cider apple varieties. Z Lebensm Unters Forsch 194:33-37
5. Brenna JT (2001) Natural intramolecular isotope measurements in physiology: elements of the case for an effort toward high-precision position-specific isotope analysis. Rapid Commun Mass Spectrom 15:1252-1262
6. Brooks SPJ (1996) Equilibrium enzymes in metabolic pathways. Biochem Cell Biol 74:411-416
7. Buchachenko AL (2003) Are chemical transformations in an enzyme-substrate complex reversible? The experience of the fractionation of isotopes in enzymatic reactions. Russ J Phys Chem 77:1298-1302
8. 18O isotope effect in the photosynthetic water splitting process. Biochim Biophys Acta 1557:77-82
9. 34S-depleted sulfide during baterial disproportionation of elemental sulfur. Science 266:1973-1975
10. Chang TL, Li WJ (1990) A calibrated measurement of the atomic weight of carbon. Chin Sci Bull 35:290-296
11. Chollet R, Vidal J, O'Leary MH (1996) Phosphoenolpyruvate carboxylase: a ubiquitous, highly regulated enzyme in plants. Annu Rev Plant Physiol Plant Mol Biol 47:273-298
12. Chu X-L, Ohmoto H (1991) Kinetics of isotope exchange reactions involving intra-and intermolecular reactions. I. Rate law for a system with two chemical compounds and three exchangeable atoms. Geochim Cosmochim Acta 55:1953-1961
13. Clark JD, O'Keefe SJ, Knowles JR (1988) Malate synthase: proof of a stepwise Claisen condensation using the double-isotope fractionation test. Biochemistry 27:5961-5971
14. DeNiro MJ, Epstein S (1977) Mechanism of carbon isotope fractionation associated with lipid biosynthesis. Science 197:261-263
15. Corso TN, Brenna JT (1997) High precision position-specific isotope analysis. Proc Natl Acad Sci USA 94:1049-1053
16. Farquhar GD, Ehleringer JR, Hubick KT (1989) Carbon isotope discrimination and photosynthesis. Annu Rev Plant Physiol Plant Mol Biol 40:503-537
17. Fronza G, Fuganti C, Serra S, Cisero M, Koziet J (2002a) Stable isotope labeling pattern of resveratrol and related natural stilbenes. J Agric Food Chem 50:2748-2754
18. 18O value of the p-OH group of L-tyrosine permits the assignment of its origin to plant or animal sources. Eur Food Res Technol 215:55-58
19. Galimov EM (1982) Interpretation of isotope fractionation in biological systems. In: Schmidt H-L, Förstel H, Heinzinger K (eds) Stable isotopes: proceedings of the 4th international conference, Jülich, March 23-26, 1981. Elsevier Scientific, Amsterdam, pp 35-47
20. Galimov EM (1985) The biological fractionation of isotopes. Academic Press, London
21. Galimov EM (2003) Isotopic criteria for identification of organic carbon on earth and meteorites. Space Sci Rev 106:249-262
22. 18OO during photosynthesis. Plant Cell Environ 23:903-915
23. 13C distributions in carbohydrates. J Biol Chem 272:5382-5387
24. Gleixner G, Schmidt H-L (1998) On-line determination of group specific isotope ratios in model compounds and aquatic humic substances by coupling pyrolysis to GC-C-IRMS. In: Stankowicz BA, Van Bergen PF (eds) Nitrogen containing macromolecules in the bio-and geosphere. (ACS symposia proceedings 707) American Chemical Society, Washington DC, pp 34-46
25. Gleixner G, Scrimgeour C, Schmidt H-L, Viola R (1998) Stable isotope distribution in the major metabolites of source and sink organs of Solanum tuberosum L.: a powerful tool in the study of metabolic partitioning in intact plants. Planta 207:241-245
26. 13C nuclear magnetic resonance studies of malate and citrate synthesis and compartmentation in higher plant cells. J Biol Chem 268:3986-3992
27. Guy RD, Fogel ML, Berry JA (1993) Photosynthetic fractionation of the stable isotopes of oxygen and carbon. Plant Physiol 101:37-47
28. Habicht KS, Canfield DE, Rethmeier J (1998) Sulfur isotope fractionation during bacterial reduction and disproportionation of thiosulfate and sulfite. Geochim Cosmochim Acta 62:2585-2595
29. Handley LL, Raven JA (1992) The use of natural abundance of nitrogen isotopes in plant physiology and ecology. Plant Cell Environ 15:965-985
30. 13C contents of sedimentary organic compounds: principles and evidence. Mar Geol 113:111-125
31. Hayes JM (2001) Fractionation of the isotopes of carbon and hydrogen in biosynthetic processes. In: Valley JW, Cole DR (eds) Stable isotope geochemistry. (Reviews in mineralogy and geochemistry, vol. 43) Mineralogical Society of America, Washington DC, pp 225-277
32. Hoefs J (1997) Stable isotope geochemistry, 4th edn. Springer, Berlin Heidelberg New York, pp 59-60, 137
33. 12C) in biological systems. Sep Sci Technol 36:1819-1914
34. 13C isotope ratios: dynamic allocation of resources in induced plants. Angew Chem Int Edn 40:2091-2093
35. Kurz LC, Nakra T, Stein R, Plungkhen W, Riley M., Hsu F, Drysdale GR (1998) Effects of changes in three catalytic residues on the relative stabilities of some of the intermediates and transition states in the citrate synthase reaction. Biochemistry 37:9724-9737
36. Kurz LC, Drysdale G, Riley M, Tomar MA, Chen J, Russell RJM, Danson MJ (2000) Kinetics and mechanism of the citrate synthase from the thermophilic archaeon Thermoplasma acidophilum. Biochemistry 39:2283-2296
37. Lance C, Rustin P (1984) The central role of malate in plant metabolism. Physiol Veg 22:625-641
38. Martin ML, Martin GJ (1991) Deuterium NMR in the study of site-specific natural isotope fractionation (SNIF-NMR). In: Diehl P, Fluck E, Günther H, Kosfeld R, Seelig J (Eds) NMR Basic Principles and Progress. Springer, Berlin, pp 1-61
39. Martin GJ, Martin ML (1999) Thirty years of flavor NMR. In: Teranishi R, Wick EL, Hornstein I (eds) Flavor chemistry: thirty years of progress. Kluwer/Plenum, New York, pp 19-30
40. 2H NMR at the natural abundance level applied to the characterisation of anetholes. J Am Chem Soc 104:2658-2659
41. Masud Z, Vallet C, Martin GJ (1999) Stable isotope characterisation of milk components and whey ethanol. J Agric Food Chem 47:4693-4699
42. Meinschein WG, Hegemann GD, Bromley BW (1984) Intramolecular distribution of stable isotopes of carbon. In: Abstract 17th international geology congress, vol 5. Moscow, pp 345-346 (cited by Galimov 2003)
43. 3 plants. Plant Physiol 84:58-60
44. Melzer E, Schmidt H-L (1987) Carbon isotope effects on the pyruvate dehydrogenase reaction and their importance for relative carbon-13 depletions in lipids. J Biol Chem 262:8159-8164
45. Monson KD, Hayes JM (1982a) Biosynthetic control of the natural abundance of carbon 13 at specific positions within fatty acids in Saccharomyces cerevisiae. J Biol Chem 257:5568-5575
46. Monson KD, Hayes JM (1982b) Carbon isotopic fractionation in the biosynthesis of bacterial fatty acids: ozonolysis of unsaturated fatty acids as a means of determining the intramolecular distribution of carbon isotopes. Geochim Cosmochim Acta 46:139-149
47. Mulholland AJ, Richards WG (1998) Modeling enzyme reaction intermediates and transition states: citrate synthase. J Phys Chem B 102:6635-6646
48. Northrop DB (2002) Effects of high pressure on enzymatic activity. Biochim Biophys Acta 1595:71-79
49. O'Leary MH (1988) Carbon isotopes in photosynthesis. Bioscience 38:328-336
50. O'Leary MH (1993) Biochemical basis of carbon isotope fractionation. In: Ehleringer JR, Hall AE, Farquhar GD (eds) Stable isotopes and plant-water relations. Academic Press, San Diego, pp 19-28
51. Olleros-Izard T (1983) Kinetische Isotopeneffekte der Arginase-und der Nitratreduktase-Reaktion. PHD thesis, Technische Universität München, Freising-Weihenstephan, Germany
52. Ovádi J (1991) Physiological significance of metabolic channelling. J Theor Biol 152:1-22
53. Polyakov VB, Mineev SD (2000) The use of Mössbauer spectroscopy in stable isotope geochemistry. Geochim Cosmochim Acta 64:849-865
54. Richter G (1996). Biochemie der Pflanzen. Georg Thieme, Stuttgart, pp 147-148
55. Rinaldi G, Meinschein WG, Hayes JM (1974) Intramolecular carbon isotopic distribution in biologically produced acetoin. Biomed Mass Spectrom 1:415-417
56. 18O equilibrium isotope effects and fractionation factors. Can J Chem 77:967-977
57. Roßmann A (2001) Determination of stable isotope ratios in food analysis. Food Rev Int 17:347-381
58. Roßmann A, Schmidt H-L (1989) Nachweis der Herkunft von Ethanol und der Zuckerung von Wein durch positionelle Wasserstoff-und Kohlenstoff-Isotopenverhältnismessung. Z Lebensm Unters Forsch 188:434-438
59. Roßmann A, Butzenlechner M, Schmidt H-L (1991) Evidence for a nonstatistical carbon isotope distribution in natural glucose. Plant Physiol 96:609-614
60. Schleucher J (1998) Intramolecular deuterium distribution and plant growth conditions. In: Griffiths H (ed) Stable isotopes: integration of biological, ecological and geochemical processes. BIOS Scientific, Oxford, pp 63-73
61. Schleucher J, Vanderveer P, Markley JL, Sharkey TD (1999) Intramolecular deuterium distributions reveal disequilibrium of chloroplast phosphoglucose isomerase. Plant Cell Environ 22:525-533
62. Schmidt H-L (1999) Isotope discriminations upon biosynthesis in natural systems: general causes and individual factors of the different bioelements. Isot Environ Health Stud 35:11-18
63. Schmidt H-L (2001) Fundamentals, prerequisites and realisations of in vivo non-statistical isotope distributions in natural compounds. In: Abstracts, 1st international symposium on isotopomers (ISI), Yokohama, Japan 2001. Japan Science and Technology Corporation (JST), Yokohama, pp 49-50
64. 2H-patterns in natural compounds. Isot Environ Health Stud 37:253-254
65. 13C-patterns in natural compounds. In: Griffiths H (ed) Stable isotopes, integration of biological, ecological and geochemical processes. BIOS Scientific, Oxford, pp 13-25
66. Schmidt H-L, Kexel H (1998) Metabolite pools and metabolic branching as factors of in vivo isotope discriminations by kinetic isotope effects. Isot Environ Health Stud 34:19-30
67. Schmidt H-L, Kexel H, Butzenlechner M, Schwarz S, Gleixner G, Thimet S, Werner RA, Gensler M (1995) Non-statistical isotope distribution in natural compounds: mirror of their biosynthesis and key for their origin assignment. In: Wada E, Yoneyama T, Minagawa M, Ando T, Fry BD (eds) Stable isotopes in the biosphere. Kyoto University Press, Japan, pp 17-35
68. Schmidt H-L, Roßmann A, Werner RA (1998) Stable isotope ratio analysis in quality control of flavourings. In: Ziegler E, Ziegler H (eds) Flavourings: production, composition, applications, regulations. Wiley-VCH, Weinheim, pp 539-594
69. Schmidt H-L, Gensler M, Weber D (2000) Nachweis eines unerlaubten Zusatzes von naturidentischen Säuren zu Obstsäften mit Hilfe von Isotopenverhältnismessungen. Fluess Obst 67:131-136
70. 18O-pattern and biosynthesis of natural plant products. Phytochemistry 58:9-32
71. 2H-patterns in natural compounds and its importance for the elucidation of biosynthetic pathways. Phytochem Rev 2
72. Sessions AL, Burgoyne TW, Schimmelmann A, Hayes JM (1999) Fractionation of hydrogen isotopes in lipid biosynthesis. Org Geochem 30:1193-1200
73. Stein LY, Yung YL (2003) Production, isotope composition, and atmospheric fate of biologically produced nitrous oxide. Annu Rev Earth Planet Sci 31:3529-356
74. Sternberg L, DeNiro MJ (1983) Biogeochemical implications of the isotope equilibrium fractionation factor between the oxygen atoms of acetone and water. Geochim Cosmochim Acta 47:2271-2274
75. Sumegi B, Sherry AD, Malloy CR, Evans C, Srere PA (1991). Is there tight channelling in the tricarboxylic acid cycle metabolon? Biochem Soc Trans 19:1002-1005
76. Thode HG (1991) Sulfur isotopes in nature and the environment: an overview. In: Krouse HR, Grinenko VA (eds) SCOPE 43. Stable isotopes: natural and anthropogenic sulfur in the environment. Wiley, Chichester, pp 1-21
77. 2O inferred from its isotopomers in the western North Pacific. Geophys Res Lett 29(3):7-1-7-4
78. Voet D, Voet JG (1992) Biochemie. VCH, Weinheim, Germany
79. x redox chemistry. Chem Rev 102:1201-1234
80. 13C-pattern of natural glycerol: origin and practical importance. J Agric Food Chem 45:2042-2046
81. Werner RA, Schmidt H-L (2002) The in vivo nitrogen isotope discrimination among organic plant compounds. Phytochemistry 61:465-484
82. Yoneyama T, Kamachi K, Yamaya T, Mae T (1993) Fractionation of nitrogen isotopes by glutamine synthetase isolated from spinach leaves. Plant Cell Physiol 34:489-491
83. Zhang B-L, Billault I, Li X, Mabon F, Remaud G, Martin ML (2002) Hydrogen isotopic profile in the characterisation of sugars: influence of the metabolic pathway. J Agric Food Chem 50:1574-1580