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Volumn 2, Issue 6, 1996, Pages 644-655

Conformational studies of chiral vinylogous sulfonamidopeptides

Author keywords

Conformation; Crystal structure; Molecular modeling; NMR spectroscopy; Sulfonamide pseudopeptides

Indexed keywords

AB INITIO CALCULATIONS; CHLOROFORM SOLUTIONS; CONFORMATIONAL FREEDOM; CONFORMATIONAL PREFERENCES; CONFORMATIONAL SEARCH; CONFORMATIONAL STUDY; SULFONAMIDE-PSEUDOPEPTIDES; VARIABLE TEMPERATURE;

EID: 84891309023     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020608     Document Type: Article
Times cited : (60)

References (67)
  • 3
  • 25
    • 84891327799 scopus 로고
    • Italian Patent Application 17 May N. MI94 A 000989; PCT Int. Appl. EP 95-01788, 11 May
    • b) C. Gennari, B. Salom, D. Potenza, Italian Patent Application 17 May 1994, N. MI94 A 000989; PCT Int. Appl. EP 95-01788, 11 May 1995;
    • (1994)
    • Gennari, C.1    Salom, B.2    Potenza, D.3
  • 38
    • 84891307980 scopus 로고    scopus 로고
    • note
    • vs-AA-OH = vinylogous sulfonyl amino acid. Defined vinylogous sulfonyl amino-acid residues are described by the vs-prefix to the three-letter code of the corresponding amino acid; for example, vs-Ala = vinylogous sulfonyl alanyl.
  • 41
    • 84891295154 scopus 로고    scopus 로고
    • note
    • The folding preferences in a solvent of this kind may be relevant for the binding of vs-peptides with proteins or other receptors in nonpolar situations (e.g., the interior of a biomembrane). Acetonitrile and DMSO, which are significantly more polar than chloroform, are known to severely disrupt intramolecular hydrogen bonding in amides (ref. [6]).
  • 42
    • 0010461163 scopus 로고
    • 3J indicates an increased population of the CH2-eclipsed rotamer. On the basis of the Boltzmann distribution law, at lower temperatures the population of the more stable rotamer should rise. Thus, a greater observed H 2-H 3 coupling constant at lower temperatures indicates that the CH 2-eclipsed rotamer (H-C*-C=C ca. 0°) is more stable, while a smaller H 2-H 3 coupling constant at lower temperatures indicates that the CN-eciipsed rotamer (N-C*-C=C ca. 0°) is more stable. See: a
    • 3J indicates an increased population of the CH2-eclipsed rotamer. On the basis of the Boltzmann distribution law, at lower temperatures the population of the more stable rotamer should rise. Thus, a greater observed H 2-H 3 coupling constant at lower temperatures indicates that the CH 2-eclipsed rotamer (H-C*-C=C ca. 0°) is more stable, while a smaller H 2-H 3 coupling constant at lower temperatures indicates that the CN-eciipsed rotamer (N-C*-C=C ca. 0°) is more stable. See: a) B. W. Gung, M. S. Gerdeman, R. A. Fouch, M. A. Wolf, J. Org. Chem. 1994, 59, 4255-4261;
    • (1994) J. Org. Chem. , vol.59 , pp. 4255-4261
    • Gung, B.W.1    Gerdeman, M.S.2    Fouch, R.A.3    Wolf, M.A.4
  • 46
    • 84891285611 scopus 로고    scopus 로고
    • The concentration independence of δ(NH) values does not in principle allow one to distinguish between a lack of aggregation and the formation of an extremely stable aggregate (e.g., vs-dipeptide, vs-tripeptide, etc.). However, this seems unlikely. For a discussion of this possibility, see footnote 13 of ref. [6 b] and footnote 16 of ref. [6 f]
    • The concentration independence of δ(NH) values does not in principle allow one to distinguish between a lack of aggregation and the formation of an extremely stable aggregate (e.g., vs-dipeptide, vs-tripeptide, etc.). However, this seems unlikely. For a discussion of this possibility, see footnote 13 of ref. [6 b] and footnote 16 of ref. [6 f].
  • 60
    • 84891293081 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC-1220-6. Copies of the data can be obtained free of charge on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: Int. code +(1223)336-033; e-mail: teched@chemcrys.cam.ac.uk).
  • 61
    • 0003633339 scopus 로고
    • B. A. Frenz and Associates, College Station, Texas, USA, and Enraf-Nonius, Delft, The Netherlands
    • a) B. A. Frenz and Associates, SDP Structure Determination Package, College Station, Texas, USA, and Enraf-Nonius, Delft, The Netherlands, 1985;
    • (1985) SDP Structure Determination Package


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.