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Volumn 9, Issue 4, 2007, Pages 644-651

Peptide-heterocycle hybrid molecules: Solid-phase-supported synthesis of substituted N-terminal 5-aminotetrazole peptides via electrocyclization of peptidic imidoylazides

Author keywords

[No Author keywords available]

Indexed keywords

5 AMINO 1H TETRAZOLE; 5-AMINO-1H-TETRAZOLE; AZIDE; HETEROCYCLIC COMPOUND; HYDANTOIN DERIVATIVE; IMIDE; PEPTIDE; TETRAZOLE DERIVATIVE; THIOUREA; UNCLASSIFIED DRUG;

EID: 34547157530     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc060119p     Document Type: Conference Paper
Times cited : (17)

References (59)
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    • For a general review, see: Sewald, N.; Jakubke, H. D. Peptides: Chemistry and Biology; Wiley-VCH: Weinheim, Germany, 2002; pp 428-502.
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    • Peptidomimetics containing heterocyclic cores have received special attention because of their metabolic stability and biological activity, see: (a) Fruchel, J. S, Jung, G. Angew. Chem, Int. Ed. Engl. 1996, 35, 17-42
    • Peptidomimetics containing heterocyclic cores have received special attention because of their metabolic stability and biological activity, see: (a) Fruchel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42.
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    • For reviews of tetrazole chemistry, see: a
    • For reviews of tetrazole chemistry, see: (a) Wittenberger, S. J. Org. Prep. Proc. Int. 1994, 26, 499-531.
    • (1994) Org. Prep. Proc. Int , vol.26 , pp. 499-531
    • Wittenberger, S.J.1
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    • Katritzky, A. R, Rees, C. V, Scriven, E. F. V, Eds, Pergamon Press: New York
    • (b) Butler, R. N. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. V., Scriven, E. F. V., Eds.; Pergamon Press: New York, 1996; Vol. 4, pp 621-678.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.4 , pp. 621-678
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    • Koldobskii, G. I. Russ. J. Org. Chem. 2006, 42, 469-486. For examples of aminotetrazole synthesis, see:
    • (c) Koldobskii, G. I. Russ. J. Org. Chem. 2006, 42, 469-486. For examples of aminotetrazole synthesis, see:
  • 25
    • 0028054343 scopus 로고    scopus 로고
    • Larsen, R. D.; King, A. O.; Chen, C. Y.; Corley, E. G.; Foster, B. S.; Roberts, F. E.; Yang, C.; Lieberman, D. R.; Reamer, R. A.; Tschaen, D. M.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1994, 59, 6391-6394. For examples of tetrazole analogs of amino acids, see:
    • (b) Larsen, R. D.; King, A. O.; Chen, C. Y.; Corley, E. G.; Foster, B. S.; Roberts, F. E.; Yang, C.; Lieberman, D. R.; Reamer, R. A.; Tschaen, D. M.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1994, 59, 6391-6394. For examples of tetrazole analogs of amino acids, see:
  • 29
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    • For recent examples of synthesis of tetrazole containing biologically important small molecules, see: a
    • For recent examples of synthesis of tetrazole containing biologically important small molecules, see: (a) Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2110-2113.
    • (2002) Angew. Chem., Int. Ed , vol.41 , pp. 2110-2113
    • Demko, Z.P.1    Sharpless, K.B.2
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    • For examples of peptidic molecules incorporating tetrazoles, see: (a) Young, M. B, Barrow, J. C, Glass, K. L, Lundell, G. F, Newton, C. L, Pellicore, J. M, Rittle, K. E, Selnick, H. G, Stauffer, K. J, Vacca, J. P, Williams, P. D, Bohn, D, Clayton, F. C, Cook, J. J, Krueger, J. A, Kuo, L. C, Lewis, S. D, Lucas, B. J, McMasters, D. R, Miller-Stein, C, Pietrak, B. L, Wallace, A. A, White, R. B, Wong, B, Yan, Y, Nantermet, P. G. J. Med. Chem. 2004, 47, 2995-3008
    • For examples of peptidic molecules incorporating tetrazoles, see: (a) Young, M. B.; Barrow, J. C.; Glass, K. L.; Lundell, G. F.; Newton, C. L.; Pellicore, J. M.; Rittle, K. E.; Selnick, H. G.; Stauffer, K. J.; Vacca, J. P.; Williams, P. D.; Bohn, D.; Clayton, F. C.; Cook, J. J.; Krueger, J. A.; Kuo, L. C.; Lewis, S. D.; Lucas, B. J.; McMasters, D. R.; Miller-Stein, C.; Pietrak, B. L.; Wallace, A. A.; White, R. B.; Wong, B.; Yan, Y.; Nantermet, P. G. J. Med. Chem. 2004, 47, 2995-3008.
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    • For a review on orthogonal protection in peptide synthesis, see
    • For a review on orthogonal protection in peptide synthesis, see: Albericio, F. Biopolymers 2000, 55, 123-139.
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    • Albericio, F.1
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    • Atomic absorption using graphite furnacing technique revealed less than 1.0 ppm of mercury in the sample
    • Atomic absorption using graphite furnacing technique revealed less than 1.0 ppm of mercury in the sample.
  • 57
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    • Gly (G, Ala (A, Leu (L, Phe (F, Met (M, Trp (W, Tyr (Y, Pro (P, Sar Sar
    • Gly (G), Ala (A), Leu (L), Phe (F), Met (M), Trp (W), Tyr (Y), Pro (P), Sar (Sar).
  • 59
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    • Protocol 14 in ref 20, p 63
    • Protocol 14 in ref 20, p 63.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.