Preparation of [1,2,3,4,5-13C 5]-5-Amino-4-oxopentanoic Acid (ALA) - Design of a Synthetic Scheme to Prepare Any 13C- and 15N-Isotopomer with High Isotopic Enrichment

European Journal of Organic Chemistry

Volumn , Issue 23, 2003, Pages 4654-4663

  Shrestha Dawadi, Prativa Bade ^a   Lugtenburg, Johan ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

Amino acids; Biosynthesis; Isotopic labelling; NMR spectroscopy

Indexed keywords

AMINOLEVULINIC ACID; BACTERIOCHLOROPHYLL; CARBON 13; CHLOROPHYLL; HEME DERIVATIVE; ISOTOPE; NITROGEN 15; PORPHYRIN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; OXYGEN TRANSPORT; PHOTOSYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0345168230     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300408     Document Type: Article

References (22)

1. L. Stryer, Biochemistry 4th ed., W. H. Freeman and Co., New York, 1995.
2. E. A. M. Schulten, J. Matysik, Alia, S. Kiihne, J. Raap, J. Lughtenburg, P. Gast, A. J. Hoff, H. J. M. de Groot, Biochemistry 2002, 41, 8708-8717.
3. R. A. Bunce, C. L. Schilling, M. Rivera, J. Labelled Compd. Radiopharm. 1997, 39, 669-675.
4. K. Iida, Y. Takao, T. Ogai, M. Kajiwara, J. Labelled Compd. Radiopharm. 1997, 39, 797-802.
5. J. Wang, A. I. Scott, Tetrahedron Lett. 1997, 38, 739-740.
6. K. Iida, S. Tokiwa, T. Ishii, M. Kajiwara, J. Labelled Compd. Radiopharm. 2002, 45, 569-576.
7. K. Iida, M. Kajiwara, J. Labelled. Compd. Radiopharm. 2002, 45, 139-143.
8. A. R. Battersby, E. Hunt, E. McDonald, J. Moron, J. Chem. Soc., Perkin Trans. 1 1973, 2917-2922.
9. H. J. Ha, S. K. Lee, Y. J. Ha, J. W. Park, Synth. Commun. 1994, 24, 2557-2562.
10. D. A. Evans, P. J. Sidebottom, J. Chem. Soc., Chem. Commun. 1978, 753-754.
11. E. Benedikt, H. P. Koest, Z. Natutforsch., Teil B 1986, 41, 1593-1594.
12. M. Van Lieshout, C. E. West, P. D. Muhilal, Y. Wang, X. Xu, R. B. Van Breemen, A. F. L. Creemers, M. A. Verhoeven, J. Lugtenburg, Am. J. Clin. Nutr. 2001, 73, 949-958.
13. Y. Wang, X. Xu, M. Van Lieshout, C. E. West, J. Lugtenburg, M. A. Verhoeven, A. F. L. Creemers, P. D. Muhilal, R. B. Van Breemen, Anal Chem. 2000, 20, 4999-5003.
14. A. F. L. Creemers, J. Lugtenburg, J. Am. Chem. Soc. 2002, 124, 6324-6334.
15. S. M. Hannick, Y. Kishi, J. Org. Chem. 1983, 48, 3833-3835.
16. J. J. Cappon, J. Baart, G. A. M. Van der Walle, J. Raap, J. Lugtenburg, Recl. Trav. Chim. Pays-Bas 1991, 110, 158-166.
17. J. Raap, W. N. E. Wolthuis, J. J. J. Hehenkamp, J. Lugtenburg, Amino Acids 1995, 8, 171-186.
18. D. E. Orr, Synthesis 1984, 618-619.
19. A. D. Abell, J. Gardiner, J. Org. Chem. 1999, 64, 9668-9672.
20. G. Gil, Tetrahedron Lett. 1984, 25, 3805-3808.
21. T. M. Werkhoven, R. van Nispen, J. Lugtenburg, Eur. J. Org. Chem. 1999, 2909-2914.
22. R. J. Bergeron, W. R. Weimar, R. Mueller, C. O. Zimmerman, B. H. McCosar, H. Yao, R. E. Smith, J. Med. Chem. 1998, 41, 3888-3900.