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Volumn 49, Issue 1, 1997, Pages 67-73

Cyclotetrapeptides and cyclopentapeptides: Occurrence and synthesis

Author keywords

Cyclisation; Cyclopentapeptides; Cyclotetrapeptides; Ring closure reaction

Indexed keywords

CYCLOPENTAPEPTIDE; CYCLOTETRAPEPTIDE; DIMER; ENZYME INHIBITOR; MONOPHENOL MONOOXYGENASE; PENTAPEPTIDE; TETRAPEPTIDE; UNCLASSIFIED DRUG;

EID: 0030999396     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.1997.tb01122.x     Document Type: Article
Times cited : (114)

References (103)
  • 1
    • 0344041221 scopus 로고    scopus 로고
    • Schmidt, U. & Weinbrenner, S. (1996) Angew. Chem. 108, 1432-1433; (1996) Angew. Chem., Int. Ed. Engl. 35, 1336-1337
    • (1996) Angew. Chem. , vol.108 , pp. 1432-1433
    • Schmidt, U.1    Weinbrenner, S.2
  • 2
    • 0029831995 scopus 로고    scopus 로고
    • Schmidt, U. & Weinbrenner, S. (1996) Angew. Chem. 108, 1432-1433; (1996) Angew. Chem., Int. Ed. Engl. 35, 1336-1337
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1336-1337
  • 12
    • 0020524076 scopus 로고
    • Waiswisz, J.M., van der Hoeven, M.G., van Peppen, J. & Zwennis, W.C.M. (1957) J. Am. Chem. Soc. 79, 4520-4521; Schipper, D. (1983) J. Antibiot. 36, 1076-1078
    • (1983) J. Antibiot. , vol.36 , pp. 1076-1078
    • Schipper, D.1
  • 15
    • 8544267880 scopus 로고    scopus 로고
    • Schmidt, U., Lieberknecht, A., Kazmaier, U. & Haslinger, E. (1990) Angew. Chem. 102, 563; Angew. Chem., Int. Ed. Engl. 29, 514
    • Angew. Chem., Int. Ed. Engl. , vol.29 , pp. 514
  • 16
    • 0021084302 scopus 로고
    • Non-stereoselective synthesis of chlamydocin: Rich, D.H. & Gardner, J. (1983) Tetrahedron Lett. 24, 5305-5308; Schmidt, U., Beuttler, T. Lieberknecht, A. & Griesser, H. (1983) Tetrahedron Lett. 24, 3573-3576
    • (1983) Tetrahedron Lett. , vol.24 , pp. 5305-5308
    • Rich, D.H.1    Gardner, J.2
  • 18
    • 0001045618 scopus 로고
    • Stereoselective synthesis of chlamydocin: Schmidt, U., Lieberknecht, A., Griesser, H. & Bartkowiak, F. (1984) Angew. Chem. 96, 310-311; (1984) Angew. Chem., Int. Ed. Engl. 23, 318-319; Schmidt, U., Lieberknecht, A., Griesser, H., Utz, R., Beutler, T. & Bartkowiak, F. (1986) Synthesis, 361-366; Kawai, M., Gardner, J.H. & Rich, D.H. (1986) Tetrahedron Lett. 27, 1877
    • (1984) Angew. Chem. , vol.96 , pp. 310-311
    • Schmidt, U.1    Lieberknecht, A.2    Griesser, H.3    Bartkowiak, F.4
  • 19
    • 0021255704 scopus 로고
    • Stereoselective synthesis of chlamydocin: Schmidt, U., Lieberknecht, A., Griesser, H. & Bartkowiak, F. (1984) Angew. Chem. 96, 310-311; (1984) Angew. Chem., Int. Ed. Engl. 23, 318-319; Schmidt, U., Lieberknecht, A., Griesser, H., Utz, R., Beutler, T. & Bartkowiak, F. (1986) Synthesis, 361-366; Kawai, M., Gardner, J.H. & Rich, D.H. (1986) Tetrahedron Lett. 27, 1877
    • (1984) Angew. Chem., Int. Ed. Engl. , vol.23 , pp. 318-319
  • 20
    • 84989111274 scopus 로고
    • Stereoselective synthesis of chlamydocin: Schmidt, U., Lieberknecht, A., Griesser, H. & Bartkowiak, F. (1984) Angew. Chem. 96, 310-311; (1984) Angew. Chem., Int. Ed. Engl. 23, 318-319; Schmidt, U., Lieberknecht, A., Griesser, H., Utz, R., Beutler, T. & Bartkowiak, F. (1986) Synthesis, 361-366; Kawai, M., Gardner, J.H. & Rich, D.H. (1986) Tetrahedron Lett. 27, 1877
    • (1986) Synthesis , pp. 361-366
    • Schmidt, U.1    Lieberknecht, A.2    Griesser, H.3    Utz, R.4    Beutler, T.5    Bartkowiak, F.6
  • 21
    • 0022651915 scopus 로고
    • Stereoselective synthesis of chlamydocin: Schmidt, U., Lieberknecht, A., Griesser, H. & Bartkowiak, F. (1984) Angew. Chem. 96, 310-311; (1984) Angew. Chem., Int. Ed. Engl. 23, 318-319; Schmidt, U., Lieberknecht, A., Griesser, H., Utz, R., Beutler, T. & Bartkowiak, F. (1986) Synthesis, 361-366; Kawai, M., Gardner, J.H. & Rich, D.H. (1986) Tetrahedron Lett. 27, 1877
    • (1986) Tetrahedron Lett. , vol.27 , pp. 1877
    • Kawai, M.1    Gardner, J.H.2    Rich, D.H.3
  • 22
  • 23
    • 8544263790 scopus 로고    scopus 로고
    • Stereoselective synthesis of WF-3161: Schmidt, U., Beutler, U. & Lieberknecht, A. (1989) Angew. Chem. 101, 344-346; Angew. Chem., Int. Ed. Engl. 28, 333-334
    • Angew. Chem., Int. Ed. Engl. , vol.28 , pp. 333-334
  • 25
    • 0016162738 scopus 로고
    • Rich, D.H. & Mathiaparanam, P. (1974) Tetrahedron Lett. 46,4037-4040; Rich, D.H., Bathnagar, P., Mathiaparanam, P., Grant, J.A. & Tam, J.P. (1978) J. Org. Chem. 43, 296-302
    • (1974) Tetrahedron Lett. , vol.46 , pp. 4037-4040
    • Rich, D.H.1    Mathiaparanam, P.2
  • 34
    • 0027397434 scopus 로고
    • Miller, S.A., Griffiths, S.L. & Seebach, D. (1993) Helv. Chim. Acta 76, 563-595; Seebach, D., Bezençon, O., Jaun, B., Pietzonka, P., Matthews, J.L., Kühnle, F.N.M. & Schweizer, W.P. (1996) Helv. Chim. Acta 79, 588-608
    • (1993) Helv. Chim. Acta , vol.76 , pp. 563-595
    • Miller, S.A.1    Griffiths, S.L.2    Seebach, D.3
  • 40
    • 8544230579 scopus 로고    scopus 로고
    • Personal communication
    • Kessler, H. (1996) Personal communication
    • (1996)
    • Kessler, H.1
  • 41
    • 8544280673 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Munich
    • Konat, R. (1996) Ph.D. Thesis, University of Munich
    • (1996)
    • Konat, R.1
  • 59
    • 8544222607 scopus 로고
    • Rothe, M. & Eisenbeiss, F. (1968) Angew. Chem. 80, 907-909; (1981) Angew. Chem. Int. Ed. Engl. 7, 883-884; Rothe, M. & Eisenbeiss, F. (1966) Z. Naturforsch., Teil B 21, 814-815
    • (1968) Angew. Chem. , vol.80 , pp. 907-909
    • Rothe, M.1    Eisenbeiss, F.2
  • 60
    • 33745366805 scopus 로고
    • Rothe, M. & Eisenbeiss, F. (1968) Angew. Chem. 80, 907-909; (1981) Angew. Chem. Int. Ed. Engl. 7, 883-884; Rothe, M. & Eisenbeiss, F. (1966) Z. Naturforsch., Teil B 21, 814-815
    • (1981) Angew. Chem. Int. Ed. Engl. , vol.7 , pp. 883-884
  • 61
    • 84986726901 scopus 로고
    • Rothe, M. & Eisenbeiss, F. (1968) Angew. Chem. 80, 907-909; (1981) Angew. Chem. Int. Ed. Engl. 7, 883-884; Rothe, M. & Eisenbeiss, F. (1966) Z. Naturforsch., Teil B 21, 814-815
    • (1966) Z. Naturforsch., Teil B , vol.21 , pp. 814-815
    • Rothe, M.1    Eisenbeiss, F.2
  • 63
    • 8544261068 scopus 로고
    • ESCOM, Leiden, in press
    • Ehrlich, A., Klose, J., Heyne, H.-U., Beyermann, M., Carpino, L.A. & Bienert, M. (1995) Peptides: Chemistry, Structure and Biology, ESCOM, Leiden, in press; Ehrlich, A., Kothemund, S., Brudel, M., Beyermann, M., Carpino, L.A. & Bienert, M. (1993) Tetrahedron Lett. 34, 4781-4784; Ehrlich, A., Brudel, M., Beyermann, M., Winter, R., Carpino, L.A. & Bienert, M. (1995) Peptides 1994. 23. Eur. Peptide Symp. Braga, Portugal, ESCOM, Leiden, pp. 167-168
    • (1995) Peptides: Chemistry, Structure and Biology
    • Ehrlich, A.1    Klose, J.2    Heyne, H.-U.3    Beyermann, M.4    Carpino, L.A.5    Bienert, M.6
  • 64
    • 0027244347 scopus 로고
    • Ehrlich, A., Klose, J., Heyne, H.-U., Beyermann, M., Carpino, L.A. & Bienert, M. (1995) Peptides: Chemistry, Structure and Biology, ESCOM, Leiden, in press; Ehrlich, A., Kothemund, S., Brudel, M., Beyermann, M., Carpino, L.A. & Bienert, M. (1993) Tetrahedron Lett. 34, 4781-4784; Ehrlich, A., Brudel, M., Beyermann, M., Winter, R., Carpino, L.A. & Bienert, M. (1995) Peptides 1994. 23. Eur. Peptide Symp. Braga, Portugal, ESCOM, Leiden, pp. 167-168
    • (1993) Tetrahedron Lett. , vol.34 , pp. 4781-4784
    • Ehrlich, A.1    Kothemund, S.2    Brudel, M.3    Beyermann, M.4    Carpino, L.A.5    Bienert, M.6
  • 65
    • 8544238448 scopus 로고
    • Ehrlich, A., Klose, J., Heyne, H.-U., Beyermann, M., Carpino, L.A. & Bienert, M. (1995) Peptides: Chemistry, Structure and Biology, ESCOM, Leiden, in press; Ehrlich, A., Kothemund, S., Brudel, M., Beyermann, M., Carpino, L.A. & Bienert, M. (1993) Tetrahedron Lett. 34, 4781-4784; Ehrlich, A., Brudel, M., Beyermann, M., Winter, R., Carpino, L.A. & Bienert, M. (1995) Peptides 1994. 23. Eur. Peptide Symp. Braga, Portugal, ESCOM, Leiden, pp. 167-168
    • (1995) Peptides 1994 , pp. 23
    • Ehrlich, A.1    Brudel, M.2    Beyermann, M.3    Winter, R.4    Carpino, L.A.5    Bienert, M.6
  • 66
    • 8544234226 scopus 로고    scopus 로고
    • Portugal, ESCOM, Leiden
    • Ehrlich, A., Klose, J., Heyne, H.-U., Beyermann, M., Carpino, L.A. & Bienert, M. (1995) Peptides: Chemistry, Structure and Biology, ESCOM, Leiden, in press; Ehrlich, A., Kothemund, S., Brudel, M., Beyermann, M., Carpino, L.A. & Bienert, M. (1993) Tetrahedron Lett. 34, 4781-4784; Ehrlich, A., Brudel, M., Beyermann, M., Winter, R., Carpino, L.A. & Bienert, M. (1995) Peptides 1994. 23. Eur. Peptide Symp. Braga, Portugal, ESCOM, Leiden, pp. 167-168
    • Eur. Peptide Symp. Braga , pp. 167-168
  • 67
    • 8544219661 scopus 로고    scopus 로고
    • personal communication; to be published
    • Bienert, M. personal communication; to be published in J. Org. Chem.
    • J. Org. Chem.
    • Bienert, M.1
  • 69
    • 8544242671 scopus 로고
    • Schmidt, U., Lieberknecht, A., Bökens, H. & Griesser, H. (1981) Angew. Chem. 93, 1121-1122; Angew. Chem., Int. Ed. Engl. 20, 1026-1027; Schmidt, U., Lieberknecht, A., Bökens, H. & Griesser, H. (1983) J. Org. Chem. 48, 2680-2685
    • (1981) Angew. Chem. , vol.93 , pp. 1121-1122
    • Schmidt, U.1    Lieberknecht, A.2    Bökens, H.3    Griesser, H.4
  • 70
    • 0001013213 scopus 로고    scopus 로고
    • Schmidt, U., Lieberknecht, A., Bökens, H. & Griesser, H. (1981) Angew. Chem. 93, 1121-1122; Angew. Chem., Int. Ed. Engl. 20, 1026-1027; Schmidt, U., Lieberknecht, A., Bökens, H. & Griesser, H. (1983) J. Org. Chem. 48, 2680-2685
    • Angew. Chem., Int. Ed. Engl. , vol.20 , pp. 1026-1027
  • 71
    • 0001300170 scopus 로고
    • Schmidt, U., Lieberknecht, A., Bökens, H. & Griesser, H. (1981) Angew. Chem. 93, 1121-1122; Angew. Chem., Int. Ed. Engl. 20, 1026-1027; Schmidt, U., Lieberknecht, A., Bökens, H. & Griesser, H. (1983) J. Org. Chem. 48, 2680-2685
    • (1983) J. Org. Chem. , vol.48 , pp. 2680-2685
    • Schmidt, U.1    Lieberknecht, A.2    Bökens, H.3    Griesser, H.4
  • 72
    • 8544229049 scopus 로고
    • Schmidt, U. & Schanbacher. U. (1983) Angew. Chem. 95, 150-151; Angew. Chem., Int. Ed. Engl. 22, 152-153; Schmidt, U. & Schanbacher, U. (1984) Liebigs Ann. Chem., 1205-1215
    • (1983) Angew. Chem. , vol.95 , pp. 150-151
    • Schmidt, U.1    Schanbacher, U.2
  • 73
    • 0001485321 scopus 로고    scopus 로고
    • Schmidt, U. & Schanbacher. U. (1983) Angew. Chem. 95, 150-151; Angew. Chem., Int. Ed. Engl. 22, 152-153; Schmidt, U. & Schanbacher, U. (1984) Liebigs Ann. Chem., 1205-1215
    • Angew. Chem., Int. Ed. Engl. , vol.22 , pp. 152-153
  • 74
    • 0021169493 scopus 로고
    • Schmidt, U. & Schanbacher. U. (1983) Angew. Chem. 95, 150-151; Angew. Chem., Int. Ed. Engl. 22, 152-153; Schmidt, U. & Schanbacher, U. (1984) Liebigs Ann. Chem., 1205-1215
    • (1984) Liebigs Ann. Chem. , pp. 1205-1215
    • Schmidt, U.1    Schanbacher, U.2
  • 77
    • 8544253174 scopus 로고
    • Schmidt, U., Lieberknecht, A., Griesser, H. & Häusler, J. (1981) Angew. Chem. 93, 272-273; Angew. Chem., Int. Ed. Engl. 20, 281-282; Schmidt, U., Lieberknecht, A., Griesser, H. & Häusler, J. (1982) Liebigs Ann. Chem., 2153-2162
    • (1981) Angew. Chem. , vol.93 , pp. 272-273
    • Schmidt, U.1    Lieberknecht, A.2    Griesser, H.3    Häusler, J.4
  • 78
    • 0001678728 scopus 로고    scopus 로고
    • Schmidt, U., Lieberknecht, A., Griesser, H. & Häusler, J. (1981) Angew. Chem. 93, 272-273; Angew. Chem., Int. Ed. Engl. 20, 281-282; Schmidt, U., Lieberknecht, A., Griesser, H. & Häusler, J. (1982) Liebigs Ann. Chem., 2153-2162
    • Angew. Chem., Int. Ed. Engl. , vol.20 , pp. 281-282
  • 82
    • 0041287511 scopus 로고
    • Schmidt, U. & Gleich, P. (1985) Angew. Chem. 97, 606-607; Angew. Chem., Int. Ed. Engl. 24, 569-570
    • (1985) Angew. Chem. , vol.97 , pp. 606-607
    • Schmidt, U.1    Gleich, P.2
  • 83
    • 8544278110 scopus 로고    scopus 로고
    • Schmidt, U. & Gleich, P. (1985) Angew. Chem. 97, 606-607; Angew. Chem., Int. Ed. Engl. 24, 569-570
    • Angew. Chem., Int. Ed. Engl. , vol.24 , pp. 569-570
  • 86
    • 0022640986 scopus 로고
    • Schmidt, U., Utz, R. & Gleich, P. Tetrahedron Lett. 26, 4367-4370; Schmidt, U. & Griesser, H. (1986) Tetrahedron Lett. 27, 163-166
    • (1986) Tetrahedron Lett. , vol.27 , pp. 163-166
    • Schmidt, U.1    Griesser, H.2
  • 87
    • 0012016526 scopus 로고
    • Schmidt, U. & Utz, R. (1984) Angew. Chem. 96, 723-724; Angew. Chem., Int. Ed. Engl. 23, 725-726; Schmidt, U., Utz, R. Lieberknecht, A., Griesser, H., Potzolli. B., Bahr, J., Wagner, K., & Fischer, P. (1987) Synthesis, 236-241
    • (1984) Angew. Chem. , vol.96 , pp. 723-724
    • Schmidt, U.1    Utz, R.2
  • 88
    • 0346005402 scopus 로고    scopus 로고
    • Schmidt, U. & Utz, R. (1984) Angew. Chem. 96, 723-724; Angew. Chem., Int. Ed. Engl. 23, 725-726; Schmidt, U., Utz, R. Lieberknecht, A., Griesser, H., Potzolli. B., Bahr, J., Wagner, K., & Fischer, P. (1987) Synthesis, 236-241
    • Angew. Chem., Int. Ed. Engl. , vol.23 , pp. 725-726
  • 91
    • 0023939819 scopus 로고
    • Schmidt, U., Kroner, M. & Griesser, H. (1988) Tetrahedron Lett. 29, 3057-3060; (1991) Synthesis, 294-300
    • (1991) Synthesis , pp. 294-300
  • 98
  • 99
    • 8544278884 scopus 로고    scopus 로고
    • Schmidt, U. & Weinbrenner, S. (1996) Angew. Chem. 108, 1432-1433; Angew. Chem., Int. Ed. Engl. 35, 1336-1337
    • Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1336-1337
  • 101
    • 0025990560 scopus 로고
    • Chen, S. & Xu, J. (1991) Tetrahedron Lett. 32, 6711-6714; for ring closure reactions see: Dudash, J., Jiang, J., Mayer, S.C. & Joullié, M.M. (1993) Synth. Commun. 23, 349-356
    • (1991) Tetrahedron Lett. , vol.32 , pp. 6711-6714
    • Chen, S.1    Xu, J.2
  • 103
    • 12044258245 scopus 로고
    • for ring closure reactions using the analoguous tetrafluorophosphate see Ref. 51
    • Carpino, L.A. (1993) J. Am. Chem. Soc. 115, 4397-4398; for ring closure reactions using the analoguous tetrafluorophosphate see Ref. 51
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4397-4398
    • Carpino, L.A.1


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