Facile synthesis of 1,1-[2H2]-2-methylaminoethane-1-sulfonic acid as a substrate for taurine α ketoglutarate dioxygenase (TauD)

Tetrahedron Letters

Volumn 50, Issue 6, 2009, Pages 611-613

  McCusker, Kevin P ^a   Klinman, Judith P ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Enzymes; Isotope effects; Mechanism; Stable isotopes

Indexed keywords

1,1 DIDEUTERO 2 METHYLAMINOETHANE SULFONIC ACID HYDROCHLORIDE; ASPARTIC ACID; DEUTERIUM; HISTIDINE; SULFONIC ACID DERIVATIVE; TAURINE ALPHA KETOGLUTARATE DIOXYGENASE; TAURINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ISOTOPE LABELING; SYNTHESIS;

EID: 57749102448     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.063     Document Type: Article

References (23)

1. Eichhorn E., vanderPloeg J.R., Kertesz M.A., and Leisinger T. J. Biol. Chem. 272 (1997) 23031-23036
2. vanderPloeg J.R., Weiss M.A., Saller E., Nashimoto H., Saito N., Kertesz M.A., and Leisinger T. J. Bacteriol. 178 (1996) 5438-5446
3. Salowe S.P., Marsh E.N., and Townsend C.A. Biochemistry 29 (1990) 6499-6508
4. Jaakkola P., Mole D.R., Tian Y.M., Wilson M.I., Gielbert J., Gaskell S.J., von Kriegsheim A., Hebestreit H.F., Mukherji M., Schofield C.J., Maxwell P.H., Pugh C.W., and Ratcliffe P.J. Science 292 (2001) 468-472
5. Falnes P.O., Johansen R.F., and Seeberg E. Nature 419 (2002) 178-182
6. Trewick S.C., Henshaw T.F., Hausinger R.P., Lindahl T., and Sedgwick B. Nature 419 (2002) 174-178
7. Aas P.A., Otterlei M., Falnes P.O., Vagbo C.B., Skorpen F., Akbari M., Sundheim O., Bjoras M., Slupphaug G., Seeberg E., and Krokan H.E. Nature 421 (2003) 859-863
8. Fukumori F., and Hausinger R.P. J. Biol. Chem. 268 (1993) 24311-24317
9. Hegg E.L., Whiting A.K., Saari R.E., McCracken J., Hausinger R.P., and Que L. Biochemistry 38 (1999) 16714-16726
10. Costas M., Mehn M.P., Jensen M.P., and Que L. Chem. Rev. 104 (2004) 939-986
11. Que L., and Ho R.Y.N. Chem. Rev. 96 (1996) 2607-2624
12. Solomon E.I., Brunold T.C., Davis M.I., Kemsley J.N., Lee S.K., Lehnert N., Neese F., Skulan A.J., Yang Y.S., and Zhou J. Chem. Rev. 100 (2000) 235-349
13. Hanauskeabel H.M., and Gunzler V. J. Theor. Biol. 94 (1982) 421-455
14. Klinman J.P. Adv. Enzymol. Rel. Areas Mol. Biol. 46 (1978) 415-494
15. Price J.C., Barr E.W., Hoffart L.M., Krebs C., and Bollinger J.M. Biochemistry 44 (2005) 8138-8147
16. Xu Y.J., Duan X.M., Li M.L., Jiang L.Q., Zhao G.H., Meng Y., and Chen L.G. Molecules 10 (2005) 259-264
17. Rodriguez M., Llinares M., Doulut S., Heitz A., and Martinez J. Tetrahedron Lett. 32 (1991) 923-926
18. The material available from Sigma is indicated as ≥98% isotopic purity in the specifications; however, individual lots, such as the one used in this study, can exceed 99.9% isotopic purity.
19. Higashiura K., Morino H., Matsuura H., Toyomaki Y., and Ienaga K. J. Chem. Soc., Perkin Trans. 1 (1989) 1479-1481
20. Uehling D.E., Donaldson K.H., Deaton D.N., Hyman C.E., Sugg E.E., Barrett D.G., Hughes R.G., Reitter B., Adkison K.K., Lancaster M.E., Lee F., Hart R., Paulik M.A., Sherman B.W., True T., and Cowan C. J. Med. Chem. 45 (2002) 567-583
21. Labeeuw O., Phansavath P., and Genet J.P. Tetrahedron Lett. 44 (2003) 6383-6386
22. Price J.C., Barr E.W., Glass T.E., Krebs C., and Bollinger J.M. J. Am. Chem. Soc. 125 (2003) 13008-13009
23. Northrop D.B. Biochemistry 20 (1981) 4056-4061