메뉴 건너뛰기




Volumn 71, Issue 19, 2006, Pages 7196-7204

Convergent approaches for the synthesis of the antitumoral peptide, Kahalalide F. study of orthogonal protecting groups

Author keywords

[No Author keywords available]

Indexed keywords

ALGAE; BIODIVERSITY; COMPOSITION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 33749003452     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060976f     Document Type: Article
Times cited : (25)

References (44)
  • 6
    • 33749004026 scopus 로고    scopus 로고
    • PCT Int. Appl. (2004) WO 2004075910, A1 20040910, CAN 141:236712, AN 2004:740175
    • Izquierdo Delso, M. A. PCT Int. Appl. (2004) WO 2004075910, A1 20040910, CAN 141:236712, AN 2004:740175.
    • Izquierdo Delso, M.A.1
  • 14
    • 0028220676 scopus 로고
    • Benz, H. Synthesis 1994, 4, 337-358.
    • (1994) Synthesis , vol.4 , pp. 337-358
    • Benz, H.1
  • 16
    • 0011763365 scopus 로고    scopus 로고
    • Chan, W. C., White, P. D., Eds.; Oxford University Press: Oxford, UK
    • (b) Barlos, K.; Gatos, D. In Fmoc Solid-Phase Peptide Synthesis; Chan, W. C., White, P. D., Eds.; Oxford University Press: Oxford, UK, 2000; pp 215-228.
    • (2000) Fmoc Solid-Phase Peptide Synthesis , pp. 215-228
    • Barlos, K.1    Gatos, D.2
  • 18
    • 0000886123 scopus 로고
    • An orthogonal protecting scheme is defined as one based on completely different classes of protecting groups such that each class of groups can be removed in any order and in the presence of all other classes of protecting groups. Barany, G.; Albericio, F. J. Am. Chem. Soc. 1985, 107, 4936-4942.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 4936-4942
    • Barany, G.1    Albericio, F.2
  • 30
    • 33748998503 scopus 로고    scopus 로고
    • note
    • If the loading is greater than 1 mmol/g, as most of the commercial available resins of this kind are, the analysis by HPLC-ESMS of the crude product shows additional peaks, corresponding to terminated sequences (see ref 26).
  • 34
    • 0034531844 scopus 로고    scopus 로고
    • The synthesis of peptides by convergent approaches and/or the cyclic peptides require the use of semi-permanent protecting groups, which must be stable to the conditions used to remove the temporal protecting group, which are those that are removed after each synthetic cycle and should be removed without affecting any permanent protecting groups, which removed in the final step of the synthetic process: Albericio, F. Biopolymers 2000, 55, 123-139.
    • (2000) Biopolymers , vol.55 , pp. 123-139
    • Albericio, F.1
  • 35
    • 0030934020 scopus 로고    scopus 로고
    • Guibe, F. Tetrahedron 1997, 53 (40), 13509-13556;
    • (1997) Tetrahedron , vol.53 , Issue.40 , pp. 13509-13556
    • Guibe, F.1
  • 36
    • 0032568384 scopus 로고    scopus 로고
    • Guibe, F. Tetrahedron 1998, 54, 2967-3042.
    • (1998) Tetrahedron , vol.54 , pp. 2967-3042
    • Guibe, F.1
  • 37
    • 33749035045 scopus 로고    scopus 로고
    • note
    • 1 is perfectly stable to the repetitive piperidine treatments during the stepwise elongation of the peptidic chain where the cycle is still not formed, the same ester bond is unstable to just one piperidine treatment once the cycle is already formed. This is a illustrative example of that the rigidity conferred by a cycle can change the physchem properties of a molecule.
  • 40
    • 33748989861 scopus 로고    scopus 로고
    • note
    • These epimers did not show any remarkable biological activity in the typical cell lines used for evaluation the antitumorals activity of Kahalalide F and its analogues.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.