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Volumn 61, Issue 2, 1996, Pages 813-815

A practical synthesis of L-azatyrosine

Author keywords

[No Author keywords available]

Indexed keywords

AZATYROSINE; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030023641     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9515079     Document Type: Article
Times cited : (30)

References (31)
  • 3
    • 0023068346 scopus 로고
    • For reviews on Ras genes and proteins see: (a) Barbacid, M. Annu Rev. Biochem. 1987, 56, 779. (b) Prendergast, G. C.; Gibbs, J. B, Adv. Cancer Res. 1993, 62, 19.
    • (1987) Annu Rev. Biochem. , vol.56 , pp. 779
    • Barbacid, M.1
  • 4
    • 0027521847 scopus 로고
    • For reviews on Ras genes and proteins see: (a) Barbacid, M. Annu Rev. Biochem. 1987, 56, 779. (b) Prendergast, G. C.; Gibbs, J. B, Adv. Cancer Res. 1993, 62, 19.
    • (1993) Adv. Cancer Res. , vol.62 , pp. 19
    • Prendergast, G.C.1    Gibbs, J.B.2
  • 27
    • 13344267504 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis is complicated by the presence of amide rotamers. The involatility of 1 made capillary GC analysis impractical, and conditions for the separation of the diastereomeric alkylation products by HPLC have not been found.
  • 29
    • 13344253251 scopus 로고    scopus 로고
    • note
    • In order to properly identify the minor enantiomer for HPLC analysis, D-azatyrosine was prepared by alkylation of the enantiomeric pseudoephedrine glycinamide ((S,S)-(+)-2) with iodide 6 followed by alkaline hydrolysis. D-Azatyrosine showed equivalent spectroscopic properties as L-azatyrosine, but opposite optical rotation.
  • 30
    • 13344253249 scopus 로고    scopus 로고
    • note
    • In contrast to other alkyl halides we have studied, small amounts of N-alkylation products are observed (<5%) during the alkylation with the highly reactive electrophile 6 whenever the reactions are conducted above -78 °C. These N-alkylation products are readily separated from the desired product by chromatography.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.