Controlled synthesis of labelled 3-L-chlorotyrosine-[ring- 13C6] and of 3,5-L-dichlorotyrosine-[ring- 13C6]

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 47, Issue 13, 2004, Pages 935-945

  Allevi, Pietro ^a   Olivero, Paola ^a   Anastasia, Mario ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

3,5 L dichlorotyrosine ring 13C6 ; 3 L chlorotyrosine ring 13C6 ; L tyrosine ring 13C6 ; Myeloperoxydase; Sulphuryl chloride

Indexed keywords

AMINO ACIDS;

3,5-L- DICHLOROTYROSINE-[RING-13C6]; 3-L-CHLOROTYROSINE-[RING-13C6]; 5-OXAZOLIDINONES; CONTROLLED SYNTHESIS; L-TYROSINE-[RING-13C6]; MYELOPEROXYDASE; ONE POT; SULPHURYL CHLORIDE;

DICHLOROMETHANE;

3 CHLOROTYROSINE C 13; 3,5 DICHLOROTYROSINE C 13; CARBON 13; DICHLOROMETHANE; MYELOPEROXIDASE; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHLORINATION; ISOTOPE LABELING; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 10344257286     PISSN: 03624803     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlcr.882     Document Type: Article

References (33)

1. (a) Klebanoff SJ. Hematol 1975; 12: 117-142.
2. (b) Harrison JE, Shultz J. J Biol Chem 1976; 251: 1371-1374.
3. Albrich JM, McCarthy CA, Hurst JK. Proc Natl Acad Sci USA 1981; 78: 210-214.
4. Winterbourn CC. Biochim Biophys Acta 1985; 840: 204-210.
5. (a) Kettle AJ. FEBS Lett 1996; 379: 103-106.
6. (b) Winterbourn CC, Kettle AJ. Free Radical Biol Med 2000; 29: 403-409 and references there reported.
7. (a) Domigan NM, Charlton TS, Duncan MW, Winterbourn CC, Kettle AJ. J Biol Chem 1995; 270: 16542-16548.
8. (b) Hazen SL, Hsu FF, Mueller DM, Crowley JR, Heinecke JW. J Clin Invest 1996; 98: 1283-1289.
9. (a) Chapman ALP, Senthilmohan R, Winterbourn CC, Kettle AJ. Arch Biochem Biophys 2000; 377: 95-100.
10. (b) Fu S, Wang H, Davies M, Deans R. J Biol Chem 2000; 275: 10851-10858 and references there cited.
11. (a) Stadtman ER. Science 1992; 257: 1220-1224.
12. (b) Ames BN, Shigenaga MK, Hagen TM. Proc Natl Acad Sci USA 1993; 90: 7915-7922.
13. (c) Berliner JA, Heinecke JW. Free Radical Biol Med 1996; 20: 707-727.
14. (a) Weiss SJN. Engl J Med 1989; 320: 365-376.
15. (b) Heinecke JW. Coron Artery Dis 1994; 5: 205-210.
16. (c) Grisham MB. Lancet 1994; 344: 859-861.
17. Hazen SL, Crowley JR, Hsu FF, Mueller DM, Heinecke JW. Free Radical Biol Med 1997; 23: 909-916.
18. Hazen SL, Heinecke JW. J Clin Invest 1997; 99: 2075-2081.
19. Himmelfarb J, McMenamin ME, Loseto G, Heinecke JW. Free Radical Biol Med 2001; 31: 1163-1169.
20. Yu G, Mason HJ, Galdi K, Wu X, Cornelius L, Zhao N, Witkus M, Ewing WR, Macor JE. Synthesis 2003; 3: 403-407.
21. Masilamani D, Rogic MM. J Org Chem 1981; 46: 4486-4489.
22. Faita G, Paio A, Quadrelli P, Rancati F, Seneci P. Tetrahedron 2001; 57: 8313-8322.
23. Allevi P, Cighetti G, Anastasia M. Tetrahedron Lett 2001; 42: 5319-5321.
24. Allevi P, Anastasia M. Tetrahedron Lett 2003; 44: 7663-7665.
25. Allevi P, Cribiù R, Anastasia M. Tetrahedron: Asymmetry 2004; 15: 1355-1358.
26. Allevi P, Cribiù R, Anastasia M. Tetrahedron Lett 2004; 45: 5841-5843.
27. Sajiki H, Kume A, Hattori K, Hirota K. Tetrahedron Lett 2002; 43: 7247-7250.
28. Gottlieb HE, Kotlyar V, Nudelman A. J Org Chem 1997; 62: 7512-7515.
29. Konig WAJ. High Resolut Chromatogr 1993; 16: 569-586.
30. Still WC, Kahn M, Mitra A. J Org Chem 1978; 43: 2923-2925.
31. Nagasawa T, Utagawa T, Goto J, Kim C-H, Tani Y, Kumagai H, Yamada H. Eur J Biochem 1981; 117: 33-40.
32. Blair West J, Wong C-H. J Org Chem 1986; 51: 2728-2735.
33. Aurelio L, Brownlee RTC, Hughes AB, Sleebs BE. Aust J Chem 2000; 53: 425-433.