메뉴 건너뛰기




Volumn 38, Issue 20, 1999, Pages 3056-3058

α-alkyl-α-amino-β-lactam peptides: Design, synthesis, and conformational features

Author keywords

Alkylations; Conformation analysis; Lactams; Peptides; Peptidomimetics

Indexed keywords

ALPHA,BETA LACTAM PEPTIDE; PEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033581577     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991018)38:20<3056::AID-ANIE3056>3.0.CO;2-J     Document Type: Article
Times cited : (35)

References (28)
  • 4
    • 0000734566 scopus 로고
    • b) A. Giannis, T. Kolter, Angew. Chem. 1993, 105, 1303-1326; Angew. Chem. Im. Ed. Engl. 1993, 32, 1244-1267;
    • (1993) Angew. Chem. , vol.105 , pp. 1303-1326
    • Giannis, A.1    Kolter, T.2
  • 5
    • 33745502124 scopus 로고
    • b) A. Giannis, T. Kolter, Angew. Chem. 1993, 105, 1303-1326; Angew. Chem. Im. Ed. Engl. 1993, 32, 1244-1267;
    • (1993) Angew. Chem. Im. Ed. Engl. , vol.32 , pp. 1244-1267
  • 6
    • 0028038601 scopus 로고
    • c) J. Gante, Angew. Chem. 1994, 106, 1780; Angew. Chem. Int. Ed. Engl. 1994, 33, 1699-1720;
    • (1994) Angew. Chem. , vol.106 , pp. 1780
    • Gante, J.1
  • 7
    • 0028038601 scopus 로고
    • c) J. Gante, Angew. Chem. 1994, 106, 1780; Angew. Chem. Int. Ed. Engl. 1994, 33, 1699-1720;
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1699-1720
  • 10
    • 0029931671 scopus 로고    scopus 로고
    • and references therein
    • A well-known approach to the formation of type I and type II β-turns is, for instance, the incorporation of L-proline at the second of the four amino acid residues: T. S. Haque, J. C. Little, S. H. Gellman, J. Am. Chem. Soc. 1996, 118, 6975-6978, and references therein.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 6975-6978
    • Haque, T.S.1    Little, J.C.2    Gellman, S.H.3
  • 11
    • 0001319466 scopus 로고
    • For a complete theoretical study on the structure of azetidin-2-ones, see a) E. Sedano, J. M. Ugalde, F. P. Cossio, C. Palomo, J. Mol. Struct. (THEOCHEM) 1988, 166, 481-486; b) J. Frau, J. Donoso, F. Muñoz, F. Garcia-Blanco, Helv. Chim. Acta 1996, 79, 353-362.
    • (1988) J. Mol. Struct. (THEOCHEM) , vol.166 , pp. 481-486
    • Sedano, E.1    Ugalde, J.M.2    Cossio, F.P.3    Palomo, C.4
  • 12
    • 0029873362 scopus 로고    scopus 로고
    • For a complete theoretical study on the structure of azetidin-2-ones, see a) E. Sedano, J. M. Ugalde, F. P. Cossio, C. Palomo, J. Mol. Struct. (THEOCHEM) 1988, 166, 481-486; b) J. Frau, J. Donoso, F. Muñoz, F. Garcia-Blanco, Helv. Chim. Acta 1996, 79, 353-362.
    • (1996) Helv. Chim. Acta , vol.79 , pp. 353-362
    • Frau, J.1    Donoso, J.2    Muñoz, F.3    Garcia-Blanco, F.4
  • 13
    • 0019443447 scopus 로고
    • For a classification of β-turns, see a) J. S. Richardson, Adv. Protein Chem. 1981, 34, 167-339; b) C. M. Wilmot, J. M. Thornton, Protein Eng. 1990, 3, 479-493.
    • (1981) Adv. Protein Chem. , vol.34 , pp. 167-339
    • Richardson, J.S.1
  • 14
    • 0025113022 scopus 로고
    • For a classification of β-turns, see a) J. S. Richardson, Adv. Protein Chem. 1981, 34, 167-339; b) C. M. Wilmot, J. M. Thornton, Protein Eng. 1990, 3, 479-493.
    • (1990) Protein Eng. , vol.3 , pp. 479-493
    • Wilmot, C.M.1    Thornton, J.M.2
  • 17
    • 0002951817 scopus 로고
    • Eds.: E. Müller, O. Bayer, Thieme, Stuttgart
    • Review; J. Backes in Houhen-Weyl, Methoden der Organischen Chemie, Band E 16B (Eds.: E. Müller, O. Bayer), Thieme, Stuttgart, 1991, p. 31.
    • (1991) Houhen-Weyl, Methoden der Organischen Chemie , vol.E , Issue.16 B , pp. 31
    • Backes, J.1
  • 18
    • 0000096261 scopus 로고
    • For the asymmetric α-alkylation of β-substituted β-lactams, see I. Ojima, Acc. Chem. Res. 1995, 28, 383-398.
    • (1995) Acc. Chem. Res. , vol.28 , pp. 383-398
    • Ojima, I.1
  • 22
    • 0345599554 scopus 로고    scopus 로고
    • note
    • max = 0.19 e Å. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-113857 (10), CCDC-113858 (4b), and CCDC-113859 (4f). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road. Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
  • 23
    • 0001199966 scopus 로고
    • For a detailed information on graph set definitions, see J. Bernstein, R. E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem. 1995, 107, 1689-1708; Angew. Chem. Int. Ed. Engl. 1995, 34, 1555-1573.
    • (1995) Angew. Chem. , vol.107 , pp. 1689-1708
    • Bernstein, J.1    Davis, R.E.2    Shimoni, L.3    Chang, N.-L.4
  • 24
    • 33748502022 scopus 로고
    • For a detailed information on graph set definitions, see J. Bernstein, R. E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem. 1995, 107, 1689- 1708; Angew. Chem. Int. Ed. Engl. 1995, 34, 1555-1573.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1555-1573
  • 25
    • 0000425457 scopus 로고
    • Interprotonic distances were calculated using the full relaxation matrix approach (MARGIGRAS + ) with data obtained from NOESY and ROESY experiments at mixing times of 200 and 400 ms. The conformation in solution was calculated by a restrained molecular mechanics minimization using the SYBYL software and TRIPOS force field; see a) B. A. Borgias, T. L. James, J. Magn. Reson. 1990, 87, 475-487; b) M. Clark, R. D. Cramer III, N. Van Opdenbosch, J. Comput. Chem. 1989, 10, 982-1012.
    • (1990) J. Magn. Reson. , vol.87 , pp. 475-487
    • Borgias, B.A.1    James, T.L.2
  • 26
    • 84988115618 scopus 로고
    • Interprotonic distances were calculated using the full relaxation matrix approach (MARGIGRAS + ) with data obtained from NOESY and ROESY experiments at mixing times of 200 and 400 ms. The conformation in solution was calculated by a restrained molecular mechanics minimization using the SYBYL software and TRIPOS force field; see a) B. A. Borgias, T. L. James, J. Magn. Reson. 1990, 87, 475-487; b) M. Clark, R. D. Cramer III, N. Van Opdenbosch, J. Comput. Chem. 1989, 10, 982-1012.
    • (1989) J. Comput. Chem. , vol.10 , pp. 982-1012
    • Clark, M.1    Cramer R.D. III2    Van Opdenbosch, N.3
  • 27
    • 84986437005 scopus 로고
    • F. Mohamadi, N. G, J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440-467; Gaussian 94, revision C.3, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, J. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defress, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian, Inc., Pittsburgh, PA. 1995.
    • (1990) J. Comput. Chem. , vol.11 , pp. 440-467
    • Mohamadi, F.1    Richards, N.G.J.2    Guida, W.C.3    Liskamp, R.4    Lipton, M.5    Caufield, C.6    Chang, G.7    Hendrickson, T.8    Still, W.C.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.