Synthesis of isotopically labelled L-phenylalanine and L-tyrosine

European Journal of Organic Chemistry

Volumn , Issue 10, 1999, Pages 2609-2621

  Raap, Jan ^a   Nieuwenhuis, Saskia ^a   Creemers, Alain ^a   Hexspoor, Sander ^a   Kragl, Udo ^b   Lugtenburg, Johan ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Amino acids; Benzonitrile; Ethyl benzoate; Isotopic labelling; Sodium phenylpyruvate

Indexed keywords

PHENYLALANINE; TYROSINE;

AMINO ACID SYNTHESIS; ARTICLE; ENANTIOMER; ISOTOPE LABELING; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032858326     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199910)1999:10<2609::aid-ejoc2609>3.0.co;2-p     Document Type: Article

References (38)

1. S. A. M. Nieuwenhuis, R. J. Hulsebosch, J. Raap, P. Gast, J. Lugtenburg, A. J. Hoff, J. Am. Chem. Soc. 1998, 120, 829.
2. T. E. Walker, C. Matheny, C. B. Storm, H. Hayden, J. Org. Chem. 1986, 51, 1175.
3. A similar reaction has previously been used for the conversion of 7-(dimethylamino)hepta-2,4,6-trienal to benzaldehyde. Since this trienal was obtained from a symmetrical precursor, this procedure was not suitable for the specific introduction of labels. A symmetrical precursor, in which the symmetry is broken by the presence of an isotope, generally does not lead to well-defined products with regard to the position of the label. H. Althoff, B. Bornowski, S. Dähne, J. Prakt. Chem. 1977, 319(6), 890.
4. R. Gebhard, Ph.D Thesis, Leiden University, The Netherlands, 1991, p. 23.
5. S. S. Malhotra, M. C. Whiting, J. Chem. Soc. 1960, 3812.
6. W. Hummel, H. Schütte, E. Schmidt, C. Wandrey, M.-R. Kula, Appl. Micmbiol. Biotechnol. 1987, 26, 409.
7. U. Kragl, A. Gödde, C. Wandrey, W. Kinzy, J. J. Cappon, J. Lugtenburg, Tetrahedron: Asymmetry 1993, 4(6), 1193.
8. F. J. Winkler, K. Kühnl, R. Medina, R. Schwarz-Kaske, H.-L. Schmidt, Isotopes Environ. Health Studies 1995, 31, 161.
9. M. Groesbeek, J. Lugtenburg, Recl. Trav. Chim. Pays-Bas 1995, 114, 403.
10. The employed nomenclature derives from the IUPAC nomenclature for this compound: 5-formyl-2,4-pentadienenitrile.
11. M Groesbeek, Ph.D Thesis, Leiden University. The Netherlands, 1993, p. 20.
12. [12a] N. L. J. M. Broekhof, F. L. Jonkers, A. van der Gen, Tetrahedron Lett. 1979, 2433.
13. [12b] N. L. J. M. Broekhof, F. L. Jonkers, A. van der Gen, Tetrahedron Lett. 1980, 2671.
14. [12c] N. L. J. M. Broekhof, A. van der Gen, Recl Trav. Chim. Pays-Bas 1984, 103, 305.
15. [12d] N. L. J. M. Broekhof, P. van Elburg, D. J. Hoff, A. van der Gen, Recl. Trav. Chim. Pays-Bas 1984, 103, 317.
16. F. J. H. M. Jansen, M. Kwestro, D. Schmitt, J. Lugtenburg, Recl. Trav. Chim. Pays-Bas 1994, 113, 552.
17. The employed nomenclature derives from the IUPAC nomenclature for this compound: ethyl 5-formyl-2.4-pentadienoate.
18. N. L. J. M. Broekhof, Ph.D Thesis, Leiden University, The Netherlands, 1982, p. 23.
19. N. L. J. M. Broekhof, P. van Elburg, A. van der Gen, Recl. Trav. Chim. Pays-Bas 1984, 103, 312.
20. R. Gebhard, K. van der Hoef, A. W. M. Lefeber, C. Erkelens, J. Lugtenburg, Recl. Trav. Chem. Pays-Bas 1990, 109, 378.
21. M. Groesbeek, J. Lugtenburg, Photochem. Photobiol. 1992, 56, 903.
22. F. J. H. M. Jansen, M. Kwestro, D. Schmitt, J. Lugtenburg, Recl. Trav. Chim. Pays-Bas 1994, 113, 552.
23. F. J. H. M. Jansen, Ph.D Thesis, Leiden University, The Netherlands, 1996, p. 23.
24. F. J. H. M. Jansen, Ph.D Thesis, Leiden University, The Netherlands, 1996, p. 57C.
25. C. Winkel, E. G. Buitenhuis, J. Lugtenburg, Recl. Trav. Chim. Pays-Bas 1989, 108, 51.
26. D. Bernard, A. Doutheau, J. Goré, Synth. Commun. 1987, 17(15), 1807.
27. [24a] K. Omura, D. Swern, Tetrahedron 1978, 34, 1651.
28. [24b] A. J. Mancuso, D. Swern, Synthesis 1981, 165.
29. F. J. H. M. Jansen, M. Kwestro, D. Schmitt, J. Lugtenburg, Recl. Trav. Chim. Pays-Bas 1994, 113, 552.
30. M. D. Fryzuk, B. Bosnich, J. Am. Chem. Soc. 1977, 99, 6262.
31. E. M. M. van den Berg, A. U. Baldew, A. T. J. W. de Goede, J. Raap, J. Lugtenburg, Recl. Trav. Chim. Pays-Bas 1988, 107, 73.
32. J. J. Cappon, K. D. Witters, J. Baart, P. J. E. Verdegem, A. C. Hoek, R. J. H. Luiten, J. Raap, J. Lugtenburg, Recl. Trav. Chim. Pays-Bas 1994, 113, 318.
33. N. L. J. M. Broekhof, P. van Elburg, A. van der Gen, Recl. Trav. Chim. Pays-Bas 1984, 103, 312.
34. D. Weuster-Botz, H. Paschold, B. Striegel, H. Gieren, M.-R. Kula, C. Wandrey, Chem. Eng. Technol. 1994, 17, 131.
35. N. Nimura, T. Kinoshita, J. Chromatogr. 1986, 352, 169.
36. P. Hušek, J. Chromatogr. 1991, 552, 289.
37. The enzyme activities given in the description of the experiments (synthesis of 1a and 1b) are those obtained under standard conditions for the respective enzymes.
38. N. L. J. M. Broekhof, F. L. Jonkers, A. van der Gen, Tetrahedron Lett. 1980, 21, 2671.