Evaluation of enantioselective gas chromatography for the determination of minute deviations from racemic composition of α-amino acids with emphasis on tyrosine: Accuracy and precision of the method

Chirality

Volumn 19, Issue 5, 2007, Pages 401-414

  Reiner, Clarissa ^a   Nicholson, Graeme J ^a   Nagel, Ulrich ^a   Schurig, Volker ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

DL amino acids; DL tyrosine; Enantioselective gas chromatography; Minute enantiomeric excess; Near racemic composition

Indexed keywords

ALPHA AMINO ACID; TYROSINE;

ACCURACY; AMINO ACID COMPOSITION; ANALYTIC METHOD; ARTICLE; CRYSTALLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL;

AMINO ACIDS; CHROMATOGRAPHY, GAS; STEREOISOMERISM; TYROSINE;

EID: 34247608673     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20390     Document Type: Article

References (57)

1. Schurig V. Review: Separation of enantiomers by gas chromatography. J Chromatogr 2001;906:275-299.
2. Schurig V. Current methods for the determination of enantiomeric compositions, Part 1: Definitions, polarimetry. Kontakte (Darmstadt) 1985:54-60.
3. Schurig V. Determination of enantiomeric purity by direct methods. In: Houben-Weyl. Methods of organic chemistry, 4th ed., Vol E21a: Stereoselective synthesis, Part A. Stuttgart, New York: Thieme; 1995. p 147-192.
4. Caglioti L, Taddei F, Holczknecht O, Hajdu C, Zekany L, Micskei K, Pályi G. Consequences of the Soai-reaction: single molecule chirality and re-evaluation of racemates. Chirality 2005, Parma, Italy. Abstracts. 2005; p 55.
5. Caglioti L, Zucchi C, Palyi G. Single-molecule chirality. Chem Today 2005;23:38-43.
6. Mislow K. Absolute asymmetric synthesis: a commentary. Coll Czechoslov Chem Commun 2003;68:849-864.
7. Soai K, Kawasaki T. Discovery of asymmetric autocatalysis with amplification of chirality and its implification in chiral homogeneity of biomolecules. Chirality 2006;18:469-478.
8. Soai K, Sato I, Shibata T. Asymmetric autocatalysis and the origin of homochirality of biomolecules. Methodol Asym Catalysis ACS Symp Ser 2004;880:85-102.
9. Shibata T, Yamamoto J, Matsumoto N, Yonekubo S, Osanai S, Soai K. Amplification of a slight enantiomeric imbalance in molecules based on asymmetric autocatalysis: the first correlation between high enantiomeric enrichment in a chiral molecule and circularly polarized light. J Am Chem Soc 1998;120:12157-12158.
10. Singleton DA, Vo LK. A few molecules can control the enantiomeric outcome. Evidence supporting absolute asymmetric synthesis using the Soai asymmetric autocatalysis. Org Lett 2003;5:4337-4339.
11. Welch CJ, Biba M, Sajonz P. Fast methods of enantiopurity determination for the Soai reaction: towards a general enantioenrichment detector? Chirality 2007;19:34-43.
12. Barron LD. Can a magnetic field induce absolute asymmetric synthesis? Science 1994;266:1491-1492.
13. Bonner WA. Parity violation and the evolution of biomolecular homochirality. Chirality 2000;12:114-126.
14. Tranter GE. The parity violating energy differences between enantiomers of α-amino acids. Mol Phys 1985;56:825-838.
15. Hodge LA, Dunning FB, Walters GK, White WH, Schroepfer GJ. Degradation of DL-leucine with longitudinally polarized electrons. Nature 1979;280:250-252.
16. Wagener K. Amplification processes for small primary differences in the properties of enantiomers. J Mol Evol 1974;4:77-84.
17. Thiemann W, Wagener K. Demonstration of the parity-violating energy difference in enantiomers. Angew Chem Int Ed 1970;9:740.
18. Shinitzky M, Nudelman F, Barda Y, Haimovitz R, Chen E, Deamer DW. Unexpected differences between D- and L-tyrosine lead to chiral enhancement in racemic mixtures. Orig Life Evol Biosph 2002;32:285-297.
19. Lahav M, Weissbuch I, Shavit E, Reiner C, Nicholson GJ, Schurig V. Parity violating energetic differences and enantiomorphous crystals - caveats; reinvestigation of tyrosine crystallization. Orig Life Evol Biosph 2006;36:151-170.
20. Nemoto A, Horie M, Honda H, Hatori K, Matsuno K. Enantiomeric excess of amino acids in hydrothermal environments. Orig Life Evol Biosph 2005;35:167-174.
21. Scolnik Y, Portnaya I, Cogan U, Haimovitz R, Fridkin M, Elitzur A, Deamer D, Shinitzky M. Subtle differences in structural transitions between poly-L- and poly-D-amino acids of equal length in water. Phys Chem Chem Phys 2006;8:333-339.
22. Meierhenrich UJ, Nguyen MJ, Barbier B, Brack A, Thiemann WH-P. Gas chromatographic separation of saturated aliphatic hydrocarbon enantiomers on permethylated β-cyclodextrin. Chirality 2003;15:S13-S16.
23. Welch CJ, Lunine JI. The chirons of titan: A search for extraterrestrial enantioenrichment. Enantiomer 2001;6:67-68.
24. Skelley AM, Scherer JR, Aubrey AD, Grover WH, Ivester RHC, Ehrenfreund P, Grunthaner FJ, Bada JL, Mathies RA. Development and evaluation of a microdevice for amino acid biomarker detection and analysis on Mars. Proc Natl Acad Sci USA 2005;102:1041-1046.
25. Goesmann F, Hilchenbach M. The gas-chromatograph mass-spectrometer (GC-MS), an instrument for in-situ measurements of volatiles in planetary atmospheres and lithospheres. Eur Space Agency 2004;SP-543:102-109.
26. Armstrong DW, Kullman JP, Chen X, Rowe M. Composition and chirality of amino acids in aerosol/dust from laboratory and residential enclosures. Chirality 2000;13:153-158.
27. Frank H, Nicholson GJ, Bayer E. Enantiomer labelling, a method for the quantitative analysis of amino acids. J Chromatogr 1978;167:187-196.
28. Edwards D, Cooper K, Dougherty RC. Asymmetric synthesis in a confined vortex: Gravitational fields can cause asymmetric synthesis. J Am Chem Soc 1980;102:381-382,7618.
29. Mead CA, Moscowitz A. Some comments on the possibility of achieving asymmetric synthesis from achiral reactants in a rotating vessel. J Am Chem Soc 1980;102:7301-7302.
30. Peres A. Asymmetric synthesis in a spinning vessel. J Am Chem Soc 1980;102:7389-7390.
31. Moradpour A, Nicoud JF, Balavoine G, Kagan H, Tsoucaris G. Photochemistry with circularly polarized light. The synthesis of optically active hexahelicene. J Am Chem Soc 1971;93:2353-2354.
32. Kagan H, Moradpour A, Nicoud JF, Balavoine G, Martin RH, Cosyn JP. Photochemistry with circularly polarised light. II. Asymmetric synthesis of octa and nonahelicene. Tetrahedr Lett 1971:2479-2482.
33. Bernstein WJ, Calvin M, Buchardt O. Absolute asymmetric synthesis. I. On the mechanism of the photochemical synthesis of nonracemic helicenes with circularly polarized light. J Am Chem Soc 1972;94:494-498.
34. Eliel EL, Wilen SH. Stereochemistry of organic compounds. New York: Wiley; 1994: p 1165.
35. Bonner W, van Dort M, Flores J. Quantitative gas chromatographic analysis of leucine enantiomers: a comparative study. Anal Chem 1974;46:2104-2107.
36. Bonner W, Blair NE. Enantiomeric phases in analytical gas chromatography. J Chromatogr 1979;169:153-159.
37. Trettin U. Wechselwirkungen von Enantiomeren in unverdünnten Flüssigkeiten. Doctoral thesis, University of Tübingen, 1993.
38. Bayer E, Allmendinger H, Enderle G, Koppenhöfer B. Anwendung von Chirasil-D-Val bei der gas-chromatographischen Analytik von Enantiomeren. Fres Z Anal Chem 1985;321:321-324.
39. Schurig V. Enantiomer analysis by complexation gas chromatography. Scope, merits and limitations. J Chromatogr 1988;441:135-153.
40. Schurig V, Glausch A. Enantiomer separation of atropisomeric polychlorinated biphenyls (PCBs) by gas chromatography on Chirasil-Dex. Naturwissenschaften 1993;80:468-469.
41. Wong CS, Hoekstra PF, Karlsson H, Backus SM, Mabury SA, Muir DCG. Enantiomer fraction of chiral organochlorine pesticides and polychlorinated biphenyls in standard and certified reference materials. Chemosphere 2002;49:1339-1347.
42. Bidleman TF, Wong F, Backe C, Södergren A, Brorström- Lundén, Helm PA, Stern GA. Chiral signatures of chlordanes indicate changing sources to the atmosphere over the past 30 years. Atmos Environ 2004;38:5963-5970.
43. Haeberle HA Wahl HG, Jakubetz H, Krause H, Schmidt R, Schurig V, Dieterich H-J. Accumulation of S(+) enantiomer in human beings after general anaesthesia with isoflurane racemate. Eur J Anaesthesiol 2002;19:641-646.
44. Schmidt R. R/S-Isofluran. Enantiomeranalytik mittels Headspace-Gaschromatographie in Patientenproben. Diploma thesis, Tübingen, 1997.
45. Schmidt R. Enantiomeranalytik chiraler Inhalationsanästhetika und ihrer Zersetzungsprodukte mittels GC. Doctoral diesis, Tübingen, 2001.
46. König WA, Krebber R, Mischnick P. Cyclodextrins as chiral stationary phases in capillary gas chromatography, Part 5: Octakis(3-O-butyryl-2,6- di-O-pentyl)-γ-cyclodextrin. J High Resolut Chromatogr 1989;12:732-738.
47. Bouche J, Verzele M. A static coating procedure for glass capillary columns. J Gas Chromatogr 1968;6:501-505.
48. La S, Ahn S, Kim JH, Goto J, Choi OK, Kim KR. Enantioseparation of chiral aromatic amino acids by capillary electrophoresis in neutral and charged cyclodextrin selector modes. Electrophoresis 2002;23:4123-4131.
49. Organic Syntheses Coll, Vol. 2. New York: Wiley; 1943. p 11-12.
50. Kitazawa M, Higuchi R, Takahashi M, Wada T, Sasabe H. Novel molecular design for second-harmonic generation: azlactone derivatives. J Phys Chem 1995;99:14784-14792.
51. Koppenhöfer B. Stereoselektivität in enzymen und modellsystemen. Habilitation thesis, University of Tübingen, 1989.
52. Schurig V, Juza M, Preschel M, Nicholson GJ, Bayer E. Gas-chromatographic enantiomer separation of proteinogenic amino acid derivatives: comparison of Chirasil-Val and Chirasil-γ-Dex used as chiral stationary phases. Enantiomer 1999;4:297-303.
53. Sicoli G, Jiang Z, Jicsinsky L, Schurig V. Modified linear dextrins ('acyclodextrins') as new chiral selectors for the gas-chromatographic separation of enantiomers. Angew Chem Int Ed 2005;44:4092-4095.
54. Schurig V. Gas chromatographic separation of enantiomers on optically active metal-complex-free stationary phases. Angew Chem Int Ed 1984;23:747-765.
55. Wätzig H, Degenhard M, Kunkel A. Strategies for capillary electrophoresis: method development and validation for pharmaceutical and biological applications. Electrophoresis 1998;19:2695-2752.
56. Hempel G, Blaschke G. Enantioselective determination of zopiclone and its metabolites in urine by capillary electrophoresis. J Chromatogr B 1996;675:139-146.
57. Grob K Jr, Grob G, Grob K. Comprehensive, standardized quality test for glass capillary columns. J Chromatogr 1978;156:1-20.