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Volumn 120, Issue 18, 1998, Pages 4334-4344

Design, synthesis, and conformational analysis of a proposed type I β- turn mimic

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; DIPEPTIDE; LACTAM DERIVATIVE; SOLVENT; TETRAPEPTIDE; TRIPEPTIDE;

EID: 0032513726     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja974023y     Document Type: Article
Times cited : (134)

References (65)
  • 3
    • 0019958979 scopus 로고
    • Hruby, V. Life Sci. 1982, 31, 189-199.
    • (1982) Life Sci. , vol.31 , pp. 189-199
    • Hruby, V.1
  • 34
    • 2642689993 scopus 로고
    • Ph.D. Thesis, University of Illinois, Urbana
    • Srinivasan, R. Ph.D. Thesis, University of Illinois, Urbana, 1994.
    • (1994)
    • Srinivasan, R.1
  • 35
    • 0023796438 scopus 로고
    • Although designed independently, our proposed turn mimic bears considerable resemblance to the type II' β-turn mimic proposed by Kemp. However, conformational analysis and attempts at incorporation of Kemp's mimic into biologically active peptides were unsuccessful due to lack of crystallinity and problems with poor solubility and tendency towards gel formation. Kemp concluded that these problems were due to the two macrocyclic amide functionalities, which were oriented perpendicular to the plane of the turn and probably facilitated β-sheet formation through intermolecular associations. Our proposed mimic should alleviate these problems through replacement of one amide functionality with a surrogate trans-olefin. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057-5060.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 5057-5060
    • Kemp, D.S.1    Stites, W.E.2
  • 61
    • 2642687955 scopus 로고    scopus 로고
    • Compound 23 was tested for biological activity in a competitive inhibition assay versus radiolabeled Substance P. Tetrapeptides 23 showed no activity, which may mean that Substance P adopts a different conformation at the receptor than that adopted by our proposed mimic
    • Compound 23 was tested for biological activity in a competitive inhibition assay versus radiolabeled Substance P. Tetrapeptides 23 showed no activity, which may mean that Substance P adopts a different conformation at the receptor than that adopted by our proposed mimic.
  • 64
    • 0001041273 scopus 로고
    • Wilson, A. J. C., Ed.; Kluwer Academic Publishers: Dordrecht
    • Wilson, A. J. C. International Tables for X-ray Crystallography; Wilson, A. J. C., Ed.; Kluwer Academic Publishers: Dordrecht, 1992; Vol. C, pp 500-502, 219-222.
    • (1992) International Tables for X-ray Crystallography , vol.100 , pp. 500-502
    • Wilson, A.J.C.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.