Efficient synthesis of optically pure Nω-alkylated L-arginines

Synthesis

Volumn , Issue 15, 2008, Pages 2391-2397

  Schade, Dennis ^a   Kotthaus, Jürke ^a   Clement, Bernd ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

DDAH; L arginine; N alkyl; Nitric oxide; NOS

Indexed keywords

DDAH; EFFICIENT SYNTHESIS; L-ARGININE; NITRIC OXIDE; NOS;

ARGININE DERIVATIVE; DIMETHYLARGININASE; HYDROLASE INHIBITOR; N DELTA [(AMINO 2,5 DIHYDRO 1H PYRROL 1 YL)METHYLIDENE]ORNITHINE BIS(TRIFLUOROACETATE); N DELTA [(AMINOMORPHOLINO)METHYLIDENE]ORNITHINE BIS(TRIFLUOROACETATE); N DELTA [[(N BENZYLOXYCARBONYLAMINO) 2,5 DIHYDRO 1H PYRROL 1 YL]METHYLIDENE] N ALPHA TERT BUTYLOXYCARBONYL ORNITHINE TERT BUTYL ESTER; N DELTA [[(N BENZYLOXYCARBONYLAMINO)MORPHOLINO]METHYLIDENE] N ALPHA TERT BUTYLOXYCARBONYL ORNITHINE TERT BUTYL ESTER; N METHOXY ARGININE BIS(TRIFLUOROACETATE); N OMEGA (2 CARBAMOYLETHYL)ARGININE BIS(TRIFLUOROACETATE); N OMEGA (2 METHOXYETHYL) ARGININE BIS(TRIFLUOROACETATE); N OMEGA (BUT 3 ENYL) ARGININE BIS(TRIFLUOROACETATE); N OMEGA ALLYL ARGININE BIS(TRIFLUOROACETATE); N OMEGA ALLYL N OMEGA' BENZYLOXYCARBONYL N ALPHA TERT BUTYLOXYCARBONYL ARGININE TERT BUTYL ESTER; N OMEGA BENZYLOXYCARBONYL N ALPHA TERT BUTOXYCARBONYL N OMEGA' (2 METH OXYETHYL)ARGININE TERT BUTYL ESTER; N OMEGA BENZYLOXYCARBONYL N ALPHA TERT BUTYLOXYCARBONYL N OMEGA (2 CARBAMOYLETHYL) ARGININE TERT BUTYL ESTER; N OMEGA BENZYLOXYCARBONYL N ALPHA TERT BUTYLOXYCARBONYL N OMEGA METHOXY ARGININE TERT BUTYL ESTER; N OMEGA BENZYLOXYCARBONYL N ALPHA TERT BUTYLOXYCARBONYL N OMEGA PROPARGYL ARGININE TERT BUTYL ESTER; N OMEGA BENZYLOXYCARBONYL N ALPHA TERT BUTYLOXYCARBONYL N OMEGA',OMEGA' (2,2,2 TRIFLUOROETHYL) ARGININE TERT BUTYL ESTER; N OMEGA BENZYLOXYCARBONYL N OMEGA' (BUT 3 ENYL) N ALPHA TERT BUTYLOXYCARBONYL ARGININE TERT BUTYL ESTER; N OMEGA PROPARGYL ARGININE BIS(TRIFLUOROACETATE); N OMEGA,OMEGA (2,2,2 TRIFLUOROETHYL)ARGININE BIS(TRIFLUOROACETATE); NITRIC OXIDE SYNTHASE; ORNITHINE;

ALKYLATION; AMINO ACID ANALYSIS; AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL STRUCTURE; CHROMATOGRAPHY; RACEMIZATION;

EID: 49649090605     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067165     Document Type: Article

References (27)

1. (a) Nitric Oxide: Biochemistry, Molecular Biology, and Therapeutic Implications, In Advances in Pharmacology, Vol. 34; Ignarro, L.; Murad, F., Eds.; Academic Press: San Diego, 1995.
2. (b) Alderton, W. K.; Cooper, C. E.; Knowles, R. G. Biochem. J. 2001, 357, 593.
3. (a) Beltowski, J.; Kedra, A. Pharmacol. Rep. 2006, 58, 159.
4. (b) Cardounel, A. J.; Cui, H.; Samouilov, A.; Johnson, W.; Kearns, P.; Tsai, A. L.; Berka, V.; Zweier, J. L. J. Biol. Chem. 2007, 282, 879.
5. Clement, B.; Kunze, T.; Heberling, S. Biochem. Biophys. Res. Commun. 2006, 349, 869.
6. Boucher, J. L.; Genet, A.; Vadon, S.; Delaforge, M.; Henry, Y.; Mansuy, D. Biochem. Biophys. Res. Commun. 1992, 187, 880.
7. Vallance, P.; Leiper, J. Nat. Rev. Drug Discovery 2002, 1, 939.
8. Zhang, H. Q.; Dixon, R. P.; Marletta, M. A.; Nikolic, D.; van Breemen, R.; Silverman, R. B. J. Am. Chem. Soc. 1997, 119, 10888.
9. Fast, W. F.; Levsky, M. E.; Marletta, M. A.; Silverman, R. B. Bioorg. Med. Chem. 1997, 5, 1601.
10. Rossiter, S.; Smith, C. L.; Malaki, M.; Nandi, M.; Gill, H.; Leiper, J. M.; Vallance, P.; Selwood, D. L. J. Med. Chem. 2005, 48, 4670.
11. Hartzoulakis, B.; Rossiter, S.; Gill, H.; O'Hara, B.; Steinke, E.; Gane, P. J.; Hurtado-Guerrero, R.; Leiper, J. M.; Vallance, P.; Rust, J. M.; Selwood, D. L. Bioorg. Med. Chem. Lett. 2007, 17, 3953.
12. Cardounel, A. J.; Cui, H.; Samouilov, A.; Johnson, W.; Kearns, P.; Tsai, A. L.; Berka, V.; Zweier, J. L. J. Biol. Chem. 2007, 282, 879.
13. Beltowski, J.; Kedra, A. Pharmacol. Rep. 2006, 58, 159.
14. Komori, Y.; Wallace, G. C.; Fukuto, J. M. Arch. Biochem. Biophys. 1994, 315, 213.
15. Kotthaus, J.; Schade, D.; Töpker-Lehmann, K.; Beitz, E.; Clement, B. Bioorg. Med. Chem. 2008, 16, 2305.
16. For a review, see: Katritzky, A. R.; Rogovoy, B. V. ARKIVOC 2005, (iv), 49.
17. Wagenaar, F. L.; Kerwin, J. F. J. Org. Chem. 1993, 58, 4331.
18. Jia, Q.; Cai, T.; Huang, M.; Li, H.; Xian, M.; Poulos, T. L.; Wang, P. G. J. Med. Chem. 2003, 46, 2271.
19. Schade, D.; Töpker-Lehmann, K.; Kotthaus, J.; Clement, B. J. Org. Chem. 2008, 73, 1025.
20. Bernatowicz, M. S.; Matsueda, G. R. Synth. Commun. 1993, 23, 657.
21. Chen, B.-c.; Shiu, S.; Yang, D.-y. J. Chin. Chem. Soc. 1998, 45, 549;
22. Chem. Abstr. 1998, 129, 276258.
23. Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamilton, A. D. J. Org. Chem. 2000, 65, 1566.
24. Martin, N. I.; Woodward, J. J.; Marletta, M. A. Org. Lett. 2006, 8, 4035.
25. Martin, N. I.; Beeson, W. T.; Woodward, J. J.; Marletta, M. A. J. Med. Chem. 2008, 51, 924.
26. Kiso, Y.; Ukawa, K.; Akita, T. J. Chem. Soc., Chem. Commun. 1980, 101.
27. Olken, N. M.; Marletta, M. A. J. Med. Chem. 1992, 35, 1137.