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Volumn , Issue 17, 2002, Pages 2616-2626

The synthesis of (2S)-4,4-difluoroglutamyl γ-peptides based on Garner's aldehyde and fluoro-reformatsky chemistry

Author keywords

Fluorescence enzyme assay; Fluoroamino acids; Fluoropeptides; Stereoselective synthesis; glutamyl hydrolase

Indexed keywords

ALDEHYDES; AMINO ACIDS; FLUORINE; HYDROLYSIS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 0036459076     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35616     Document Type: Article
Times cited : (16)

References (48)
  • 1
    • 2242491902 scopus 로고    scopus 로고
    • Current Address: Department of Immunology NB-30, The Cleveland Clinic Foundation, 9500 Euclid Avenue, Cleveland, OH, 44195
    • Current Address: Department of Immunology NB-30, The Cleveland Clinic Foundation, 9500 Euclid Avenue, Cleveland, OH, 44195.
  • 15
  • 16
    • 0000083882 scopus 로고
    • Blakley, R. L.; Benkovic, S. J., Eds.; Wiley: New York
    • McGuire, J. J.; Coward, J. K. In Folates and Pterins, Vol. 1; Blakley, R. L.; Benkovic, S. J., Eds.; Wiley: New York, 1984, 135.
    • (1984) Folates and Pterins , vol.1 , pp. 135
    • McGuire, J.J.1    Coward, J.K.2
  • 40
    • 0037179189 scopus 로고    scopus 로고
    • (b) Note added in proof: A recently published correction to Ref. 39a indicates that the reported synthesis of L-4,4-difluoroglutamine is in error; the product isolated was L-4,4-difluoroglutamic acid, see: Meffre, P.; Dave, R. H.; Leroy, J.; Badet, B. Tetrahedron Lett. 2002, 43, 6279. Thus, removal of the Cbz group in 15 (Scheme 3) by catalytic hydrogenolysis in modest yield (ca 50%) as reported for the racemic material in Ref. 38 represents the only tenable route to the synthesis of L-4,4-difluoroglutamine reported to date.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 6279
    • Meffre, P.1    Dave, R.H.2    Leroy, J.3    Badet, B.4
  • 47
    • 2242437288 scopus 로고    scopus 로고
    • (University of Michigan, Ann Arbor), unpublished results
    • Pankuch, J.; Hui, M. (University of Michigan, Ann Arbor), unpublished results.
    • Pankuch, J.1    Hui, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.