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Volumn 73, Issue 3, 2008, Pages 1025-1030

Synthetic approaches to Nδ-methylated L-arginine, N ω-hydroxy-L-arginine, L-citrulline, and Nδ- cyano-L-ornithine

Author keywords

[No Author keywords available]

Indexed keywords

NITRIC OXIDE SYNTHASES; PHYSIOLOGICAL INHIBITORS;

EID: 38849108141     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702150d     Document Type: Article
Times cited : (27)

References (43)
  • 1
    • 0004097804 scopus 로고
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    • (a) Ignarro, L.; Murad, F., Eds. Nitric Oxide: Biochemistry, molecular biology, and therapeutic implications. In Advances in Pharmacology; Academic Press: San Diego, CA, 1995; Vol. 34.
    • (1995) Advances in Pharmacology , vol.34
  • 2
    • 0035425503 scopus 로고    scopus 로고
    • Nitric oxide synthases: Structures, function and inhibition
    • (b) Alderton, W. K.; Cooper, C. E.; Knowles, R. G. Nitric oxide synthases: structures, function and inhibition. Biochem. J. 2001, 357, 593.
    • (2001) Biochem. J , vol.357 , pp. 593
    • Alderton, W.K.1    Cooper, C.E.2    Knowles, R.G.3
  • 14
    • 38849090362 scopus 로고    scopus 로고
    • Hydroxylamine base was set free from its hydrochloride with sodium ethanolate. Steudel, R.; Schenk, P. W. In Handbuch der präparativen anorganischen Chemie, 3rd ed.; Brauer, G., Ed.; Ferdinand Enke Verlag: Stuttgart, Germany, 1975; 1, p 464.
    • Hydroxylamine base was set free from its hydrochloride with sodium ethanolate. Steudel, R.; Schenk, P. W. In Handbuch der präparativen anorganischen Chemie, 3rd ed.; Brauer, G., Ed.; Ferdinand Enke Verlag: Stuttgart, Germany, 1975; Vol. 1, p 464.
  • 17
    • 0028670616 scopus 로고    scopus 로고
    • ω-hydroxy-L-arginine: Clement, B.; Schnörwangen, E.; Kämpchen, T.; Mordvintcev, P.; Mülsch, A. Arch. Pharm. 1994, 327, 793.
    • ω-hydroxy-L-arginine: Clement, B.; Schnörwangen, E.; Kämpchen, T.; Mordvintcev, P.; Mülsch, A. Arch. Pharm. 1994, 327, 793.
  • 18
    • 38849106556 scopus 로고    scopus 로고
    • 4, pH 1.5.
    • 4, pH 1.5.
  • 22
    • 0034629285 scopus 로고    scopus 로고
    • Diethylboryl complexation procedure under these conditions first described by
    • (a) Diethylboryl complexation procedure under these conditions first described by Garcia et al. Tetrahedron: Asymmetry 2000, 11, 991.
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 991
    • Garcia1
  • 24
    • 38849185684 scopus 로고    scopus 로고
    • Described by Luzzi and Marletta for the diethylboryl complexes
    • (c) Described by Luzzi and Marletta for the diethylboryl complexes.
  • 32
    • 38849202147 scopus 로고    scopus 로고
    • Protocols of different authors for synthetic intermediates leading to 10 and the final deprotecting step were considered and evaluated. Detailed synthetic protocols are provided in the Supporting Information along with the references. Note: So far reported characterization data were in most cases incomplete and are summarized in the Supporting Information.
    • Protocols of different authors for synthetic intermediates leading to 10 and the final deprotecting step were considered and evaluated. Detailed synthetic protocols are provided in the Supporting Information along with the references. Note: So far reported characterization data were in most cases incomplete and are summarized in the Supporting Information.
  • 34
    • 34547102732 scopus 로고    scopus 로고
    • Further articles reporting about similar application of 9-BBN-H: Cudic, M.; Mari, F.; Fields, G. B. J. Org. Chem. 2007, 72, 5581.
    • (b) Further articles reporting about similar application of 9-BBN-H: Cudic, M.; Mari, F.; Fields, G. B. J. Org. Chem. 2007, 72, 5581.
  • 37
    • 38849177834 scopus 로고    scopus 로고
    • A complete spectroscopic characterization of the herein described complexed intermediates is given in the Supporting Information, including 2D NMR experiments with 9-BBN complexes
    • A complete spectroscopic characterization of the herein described complexed intermediates is given in the Supporting Information, including 2D NMR experiments with 9-BBN complexes.
  • 38
    • 38849198921 scopus 로고    scopus 로고
    • 9-BBN complex 12 was examined in terms of pH stability HPTLC experiments, data not shown, It withstands even concentrated TFA over several hours, making it suitable in orthogonal sets, but hydrolyzes rapidly in dilute HCl as well as at pH > 6. Maximum stability was observed at pH 2-4
    • 9-BBN complex 12 was examined in terms of pH stability (HPTLC experiments, data not shown). It withstands even concentrated TFA over several hours, making it suitable in orthogonal sets, but hydrolyzes rapidly in dilute HCl as well as at pH > 6. Maximum stability was observed at pH 2-4.
  • 39
    • 0010316605 scopus 로고    scopus 로고
    • Hydroxyguanidines are known to be most stable as salts of strong acids. Literature: (a) hydroxyguanidine: Walker, J. B.; Walker, M. S. J. Biol. Chem. 1959, 234, 1481.
    • Hydroxyguanidines are known to be most stable as salts of strong acids. Literature: (a) hydroxyguanidine: Walker, J. B.; Walker, M. S. J. Biol. Chem. 1959, 234, 1481.
  • 40
    • 0029819906 scopus 로고    scopus 로고
    • ω-hydroxy-L-arginine: Fukuto, J. M. Meth. Enzymol. 1996, 268, 365.
    • ω-hydroxy-L-arginine: Fukuto, J. M. Meth. Enzymol. 1996, 268, 365.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.