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Volumn 68, Issue 24, 2003, Pages 9247-9254

Derivatized Amino Acids Relevant to Native Peptide Synthesis by Chemical Ligation and Acyl Transfer

Author keywords

[No Author keywords available]

Indexed keywords

LIGATION-ACYL TRANSFER METHOD; PEPTIDE SEGMENT COUPLING;

EID: 0345686489     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030192r     Document Type: Article
Times cited : (31)

References (60)
  • 30
    • 0344327892 scopus 로고    scopus 로고
    • note
    • Our preliminary studies (see: Coltart, D. M., Ph.D. Thesis, University of Alberta, 2000) were based on thiophenolic and 1-phenyl-2-mercaptoethyl systems exemplified by i and ii. Work on the former was stopped when similar studies by Dawson and Offer (ref 5r) were published. A noteworthy feature of ii (and 2.1) is that the mercapto group ultimately released is an alkyl thiol and, as such, is more nucleophilic than an aryl thiol (cf. i).
  • 31
    • 0345190342 scopus 로고    scopus 로고
    • PCT Int. Appl. WO 2002/20557
    • The possibility of preparing compounds of type 2.1 by reductive amination or by halide displacement (cf. the present method) is shown in a generic scheme in two patents: (a) Botti, P.; Bradburne, J. A.; Kent, S. B. H.; Low, D. W. PCT Int. Appl. WO 2002/20557.
    • Botti, P.1    Bradburne, J.A.2    Kent, S.B.H.3    Low, D.W.4
  • 36
    • 0345622527 scopus 로고    scopus 로고
    • note
    • 2, rt, 6 h) and less efficient (64% of 4.3) than the route of Scheme 4.
  • 42
    • 0345190341 scopus 로고    scopus 로고
    • note
    • 19F δ -69.6 and -69.4 ppm).
  • 46
    • 0344327891 scopus 로고    scopus 로고
    • note
    • 2O-DMAP-t-BuOH (ref 22) gave partially racemized material.
  • 47
    • 0345622526 scopus 로고    scopus 로고
    • note
    • (b) Transesterification with tert-butyl acetate (ref 23) was very slow and proceeded in poor yield.
  • 53
    • 0345190340 scopus 로고    scopus 로고
    • note
    • (b) L-Alanine tert-butyl ester is commercially available.
  • 54
    • 0344327890 scopus 로고    scopus 로고
    • note
    • 3OD, 100 MHz) δ 41.5 (t'), 44.3 (t'), 128.5 (d'), 128.7 (d'), 129.6 (d'), 139.4 (s'), 167.1 (s').
  • 57
    • 0345190339 scopus 로고    scopus 로고
    • note
    • 2NEt).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.