메뉴 건너뛰기




Volumn 37, Issue 8, 1998, Pages 1086-1089

Facile synthesis of cyclic tetrapeptides from nonactivated peptide esters on metal centers

Author keywords

Copper; Cyclopeptides; Nickel; Palladium; Peptides

Indexed keywords


EID: 0032482050     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980504)37:8<1086::AID-ANIE1086>3.0.CO;2-V     Document Type: Article
Times cited : (82)

References (42)
  • 1
    • 0001631118 scopus 로고
    • H. Kessler, Angew. Chem. 1982, 94, 509-520; Angew. Chem. Int. Ed. Engl. 1982, 21, 512-523.
    • (1982) Angew. Chem. , vol.94 , pp. 509-520
    • Kessler, H.1
  • 2
    • 0020163940 scopus 로고
    • H. Kessler, Angew. Chem. 1982, 94, 509-520; Angew. Chem. Int. Ed. Engl. 1982, 21, 512-523.
    • (1982) Angew. Chem. Int. Ed. Engl. , vol.21 , pp. 512-523
  • 4
    • 0001241742 scopus 로고    scopus 로고
    • R. Haubner, D. Finsinger, H. Kessler, Angew. Chem. 1997, 109, 1440-1456; Angew. Chem. Int. Ed. Engl. 1997, 36, 1374-1389; C. M. Deber, V. Madison, E. R. Blout, Acc. Chem. Res. 1976, 9, 106-112.
    • (1997) Angew. Chem. , vol.109 , pp. 1440-1456
    • Haubner, R.1    Finsinger, D.2    Kessler, H.3
  • 5
    • 0030768536 scopus 로고    scopus 로고
    • R. Haubner, D. Finsinger, H. Kessler, Angew. Chem. 1997, 109, 1440-1456; Angew. Chem. Int. Ed. Engl. 1997, 36, 1374-1389; C. M. Deber, V. Madison, E. R. Blout, Acc. Chem. Res. 1976, 9, 106-112.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 1374-1389
  • 6
    • 33847798685 scopus 로고
    • R. Haubner, D. Finsinger, H. Kessler, Angew. Chem. 1997, 109, 1440-1456; Angew. Chem. Int. Ed. Engl. 1997, 36, 1374-1389; C. M. Deber, V. Madison, E. R. Blout, Acc. Chem. Res. 1976, 9, 106-112.
    • (1976) Acc. Chem. Res. , vol.9 , pp. 106-112
    • Deber, C.M.1    Madison, V.2    Blout, E.R.3
  • 7
    • 0001625501 scopus 로고
    • K. D. Kopple, J. Pharm. Sci. 1972, 61, 1345-1356; V. J. Hruby, Life Sci. 1982, 31, 189-199; F. Al-Obedi, A. M. del L. Castrucci, M. E. Hadley, V. J. Hruby, J. Med. Chem. 1989, 32, 2555-2561.
    • (1972) J. Pharm. Sci. , vol.61 , pp. 1345-1356
    • Kopple, K.D.1
  • 8
    • 0019958979 scopus 로고
    • K. D. Kopple, J. Pharm. Sci. 1972, 61, 1345-1356; V. J. Hruby, Life Sci. 1982, 31, 189-199; F. Al-Obedi, A. M. del L. Castrucci, M. E. Hadley, V. J. Hruby, J. Med. Chem. 1989, 32, 2555-2561.
    • (1982) Life Sci. , vol.31 , pp. 189-199
    • Hruby, V.J.1
  • 12
    • 0000703784 scopus 로고
    • c) U. Schmidt, Pure Appl. Chem. 1986, 58, 295-304; U. Schmidt, J. Langner, J. Peptide Res. 1997, 49, 67, and references therein.
    • (1986) Pure Appl. Chem. , vol.58 , pp. 295-304
    • Schmidt, U.1
  • 13
    • 0030999396 scopus 로고    scopus 로고
    • and references therein
    • c) U. Schmidt, Pure Appl. Chem. 1986, 58, 295-304; U. Schmidt, J. Langner, J. Peptide Res. 1997, 49, 67, and references therein.
    • (1997) J. Peptide Res. , vol.49 , pp. 67
    • Schmidt, U.1    Langner, J.2
  • 14
    • 84985653969 scopus 로고
    • a) E. R. Blout, Biopolymers 1981, 20, 1901-1902; N. J. Manesis, M. Goodmann, J. Org. Chem. 1987, 52, 5331-5341;
    • (1981) Biopolymers , vol.20 , pp. 1901-1902
    • Blout, E.R.1
  • 15
  • 18
    • 0028222937 scopus 로고
    • d) L. A. Carpino, A. El-Faham, F. Albericio, Tetrahedron Lett. 1994, 35, 2279-2282; S. A. Kabee, N. A. Solé, C. R. Johnson, D. Hudson, G. Barang, F. Albericio, ibid. 1993, 34, 1549-1552;
    • (1994) Tetrahedron Lett. , vol.35 , pp. 2279-2282
    • Carpino, L.A.1    El-Faham, A.2    Albericio, F.3
  • 20
    • 0012297150 scopus 로고
    • e) W. F. De Grado, E. T. Kaiser, J. Org. Chem. 1980, 45, 1295-1300; ibid. 1982, 47, 3258-3261; G. Ösapay, A. Profit, J. W. Taylor, Tetrahedron Lett. 1990, 31, 6121-6124; G. Ösapay, J. W. Taylor, J. Am. Chem. Soc. 1990, 112, 6046-6051; M. Xu, N. Nishino, H. Mihara, T. Fujimoto, N. Izumiya, Chem. Lett. 1992, 191-194;
    • (1980) J. Org. Chem. , vol.45 , pp. 1295-1300
    • De Grado, W.F.1    Kaiser, E.T.2
  • 21
    • 0000081593 scopus 로고
    • e) W. F. De Grado, E. T. Kaiser, J. Org. Chem. 1980, 45, 1295-1300; ibid. 1982, 47, 3258-3261; G. Ösapay, A. Profit, J. W. Taylor, Tetrahedron Lett. 1990, 31, 6121-6124; G. Ösapay, J. W. Taylor, J. Am. Chem. Soc. 1990, 112, 6046-6051; M. Xu, N. Nishino, H. Mihara, T. Fujimoto, N. Izumiya, Chem. Lett. 1992, 191-194;
    • (1982) J. Org. Chem. , vol.47 , pp. 3258-3261
  • 22
    • 0025011819 scopus 로고
    • e) W. F. De Grado, E. T. Kaiser, J. Org. Chem. 1980, 45, 1295-1300; ibid. 1982, 47, 3258-3261; G. Ösapay, A. Profit, J. W. Taylor, Tetrahedron Lett. 1990, 31, 6121-6124; G. Ösapay, J. W. Taylor, J. Am. Chem. Soc. 1990, 112, 6046-6051; M. Xu, N. Nishino, H. Mihara, T. Fujimoto, N. Izumiya, Chem. Lett. 1992, 191-194;
    • (1990) Tetrahedron Lett. , vol.31 , pp. 6121-6124
    • Ösapay, G.1    Profit, A.2    Taylor, J.W.3
  • 23
    • 0025007537 scopus 로고
    • e) W. F. De Grado, E. T. Kaiser, J. Org. Chem. 1980, 45, 1295-1300; ibid. 1982, 47, 3258-3261; G. Ösapay, A. Profit, J. W. Taylor, Tetrahedron Lett. 1990, 31, 6121-6124; G. Ösapay, J. W. Taylor, J. Am. Chem. Soc. 1990, 112, 6046-6051; M. Xu, N. Nishino, H. Mihara, T. Fujimoto, N. Izumiya, Chem. Lett. 1992, 191-194;
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6046-6051
    • Ösapay, G.1    Taylor, J.W.2
  • 24
    • 0002283181 scopus 로고
    • e) W. F. De Grado, E. T. Kaiser, J. Org. Chem. 1980, 45, 1295-1300; ibid. 1982, 47, 3258-3261; G. Ösapay, A. Profit, J. W. Taylor, Tetrahedron Lett. 1990, 31, 6121-6124; G. Ösapay, J. W. Taylor, J. Am. Chem. Soc. 1990, 112, 6046-6051; M. Xu, N. Nishino, H. Mihara, T. Fujimoto, N. Izumiya, Chem. Lett. 1992, 191-194;
    • (1992) Chem. Lett. , pp. 191-194
    • Xu, M.1    Nishino, N.2    Mihara, H.3    Fujimoto, T.4    Izumiya, N.5
  • 26
    • 0000916479 scopus 로고
    • W. Beck, R. Krämer, Angew. Chem. 1991, 103, 1492-1493; Angew. Chem. Int. Ed. Engl. 1991, 30, 1467-1469; R. Krämer, M. Maurus, K. Polborn, K. Sünkel, C. Robl, W. Beck, Chem. Eur. J. 1996, 2, 1518-1526.
    • (1991) Angew. Chem. , vol.103 , pp. 1492-1493
    • Beck, W.1    Krämer, R.2
  • 27
    • 33748217160 scopus 로고
    • W. Beck, R. Krämer, Angew. Chem. 1991, 103, 1492-1493; Angew. Chem. Int. Ed. Engl. 1991, 30, 1467-1469; R. Krämer, M. Maurus, K. Polborn, K. Sünkel, C. Robl, W. Beck, Chem. Eur. J. 1996, 2, 1518-1526.
    • (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 1467-1469
  • 32
    • 0344134585 scopus 로고    scopus 로고
    • note
    • -3; all calculations using the program SHELXL-97. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-100954. 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).
  • 33
    • 0002126543 scopus 로고
    • N. F. Curtis, Coord. Chem. Rev. 1968, 3, 3-47; D. S. C. Black, A. J. Hartshorn, ibid. 1972, 9, 219-274; J. J. Christensen, D. J. Eatough, R. M. Izatt, ibid. 1974, 74, 351-384; D. H. Busch, N. A. Stephenson, ibid. 1990, 100, 119-154; P. Comba, N. F. Curtis, G. A. Lawrance, A. M. Sargeson, B. W. Skelton, A. H. White, Inorg. Chem. 1986, 25, 4260-4267.
    • (1968) Coord. Chem. Rev. , vol.3 , pp. 3-47
    • Curtis, N.F.1
  • 34
    • 0013106989 scopus 로고
    • N. F. Curtis, Coord. Chem. Rev. 1968, 3, 3-47; D. S. C. Black, A. J. Hartshorn, ibid. 1972, 9, 219-274; J. J. Christensen, D. J. Eatough, R. M. Izatt, ibid. 1974, 74, 351-384; D. H. Busch, N. A. Stephenson, ibid. 1990, 100, 119-154; P. Comba, N. F. Curtis, G. A. Lawrance, A. M. Sargeson, B. W. Skelton, A. H. White, Inorg. Chem. 1986, 25, 4260-4267.
    • (1972) Coord. Chem. Rev. , vol.9 , pp. 219-274
    • Black, D.S.C.1    Hartshorn, A.J.2
  • 35
    • 33847804075 scopus 로고
    • N. F. Curtis, Coord. Chem. Rev. 1968, 3, 3-47; D. S. C. Black, A. J. Hartshorn, ibid. 1972, 9, 219-274; J. J. Christensen, D. J. Eatough, R. M. Izatt, ibid. 1974, 74, 351-384; D. H. Busch, N. A. Stephenson, ibid. 1990, 100, 119-154; P. Comba, N. F. Curtis, G. A. Lawrance, A. M. Sargeson, B. W. Skelton, A. H. White, Inorg. Chem. 1986, 25, 4260-4267.
    • (1974) Coord. Chem. Rev. , vol.74 , pp. 351-384
    • Christensen, J.J.1    Eatough, D.J.2    Izatt, R.M.3
  • 36
    • 0000983603 scopus 로고
    • N. F. Curtis, Coord. Chem. Rev. 1968, 3, 3-47; D. S. C. Black, A. J. Hartshorn, ibid. 1972, 9, 219-274; J. J. Christensen, D. J. Eatough, R. M. Izatt, ibid. 1974, 74, 351-384; D. H. Busch, N. A. Stephenson, ibid. 1990, 100, 119-154; P. Comba, N. F. Curtis, G. A. Lawrance, A. M. Sargeson, B. W. Skelton, A. H. White, Inorg. Chem. 1986, 25, 4260-4267.
    • (1990) Coord. Chem. Rev. , vol.100 , pp. 119-154
    • Busch, D.H.1    Stephenson, N.A.2
  • 37
    • 33845376350 scopus 로고
    • N. F. Curtis, Coord. Chem. Rev. 1968, 3, 3-47; D. S. C. Black, A. J. Hartshorn, ibid. 1972, 9, 219-274; J. J. Christensen, D. J. Eatough, R. M. Izatt, ibid. 1974, 74, 351-384; D. H. Busch, N. A. Stephenson, ibid. 1990, 100, 119-154; P. Comba, N. F. Curtis, G. A. Lawrance, A. M. Sargeson, B. W. Skelton, A. H. White, Inorg. Chem. 1986, 25, 4260-4267.
    • (1986) Inorg. Chem. , vol.25 , pp. 4260-4267
    • Comba, P.1    Curtis, N.F.2    Lawrance, G.A.3    Sargeson, A.M.4    Skelton, B.W.5    White, A.H.6
  • 39
    • 33845557812 scopus 로고
    • J. S. Rybka, D. W. Margerum, Inorg. Chem. 1980, 19, 2784-2790; ibid. 1981, 20, 1453-1458.
    • (1981) Inorg. Chem. , vol.20 , pp. 1453-1458
  • 42
    • 0021159751 scopus 로고
    • M. Bodanszky, Principles of Peptide Synthesis, 2nd ed., Springer, Berlin, 1994; V. Dourtoglou, B. Gross, Synthesis 1984, 572-574.
    • (1984) Synthesis , pp. 572-574
    • Dourtoglou, V.1    Gross, B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.