메뉴 건너뛰기




Volumn , Issue 9, 1997, Pages 1098-1108

Selective enzymatic removal of protecting groups from phosphopeptides: Chemoenzymatic synthesis of a characteristic phosphopeptide fragment of the raf-1 kinase

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHOPEPTIDE; TRIACYLGLYCEROL LIPASE;

EID: 0030863953     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1306     Document Type: Article
Times cited : (21)

References (43)
  • 1
    • 0003942446 scopus 로고    scopus 로고
    • VCH: Weinheim
    • Protein Phosphorylation, Marks, F., Ed.; VCH: Weinheim, 1996. Krebs, E. G. Angew. Chem. 1993, 105, 1173; Angew. Chem., Int. Ed. Engl. 1993, 32, 1122. Fischer, E. H. Angew. Chem. 1993, 105, 1181; Angew. Chem., Int. Ed. Engl. 1993, 105, 1130. Cohen, P. Nature 1982, 296, 613.
    • (1996) Protein Phosphorylation
    • Marks, F.1
  • 2
    • 0011830250 scopus 로고
    • Protein Phosphorylation, Marks, F., Ed.; VCH: Weinheim, 1996. Krebs, E. G. Angew. Chem. 1993, 105, 1173; Angew. Chem., Int. Ed. Engl. 1993, 32, 1122. Fischer, E. H. Angew. Chem. 1993, 105, 1181; Angew. Chem., Int. Ed. Engl. 1993, 105, 1130. Cohen, P. Nature 1982, 296, 613.
    • (1993) Angew. Chem. , vol.105 , pp. 1173
    • Krebs, E.G.1
  • 3
    • 33749082568 scopus 로고
    • Protein Phosphorylation, Marks, F., Ed.; VCH: Weinheim, 1996. Krebs, E. G. Angew. Chem. 1993, 105, 1173; Angew. Chem., Int. Ed. Engl. 1993, 32, 1122. Fischer, E. H. Angew. Chem. 1993, 105, 1181; Angew. Chem., Int. Ed. Engl. 1993, 105, 1130. Cohen, P. Nature 1982, 296, 613.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 1122
  • 4
    • 0011911258 scopus 로고
    • Protein Phosphorylation, Marks, F., Ed.; VCH: Weinheim, 1996. Krebs, E. G. Angew. Chem. 1993, 105, 1173; Angew. Chem., Int. Ed. Engl. 1993, 32, 1122. Fischer, E. H. Angew. Chem. 1993, 105, 1181; Angew. Chem., Int. Ed. Engl. 1993, 105, 1130. Cohen, P. Nature 1982, 296, 613.
    • (1993) Angew. Chem. , vol.105 , pp. 1181
    • Fischer, E.H.1
  • 5
    • 0000894876 scopus 로고
    • Protein Phosphorylation, Marks, F., Ed.; VCH: Weinheim, 1996. Krebs, E. G. Angew. Chem. 1993, 105, 1173; Angew. Chem., Int. Ed. Engl. 1993, 32, 1122. Fischer, E. H. Angew. Chem. 1993, 105, 1181; Angew. Chem., Int. Ed. Engl. 1993, 105, 1130. Cohen, P. Nature 1982, 296, 613.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.105 , pp. 1130
  • 6
    • 0019982538 scopus 로고
    • Protein Phosphorylation, Marks, F., Ed.; VCH: Weinheim, 1996. Krebs, E. G. Angew. Chem. 1993, 105, 1173; Angew. Chem., Int. Ed. Engl. 1993, 32, 1122. Fischer, E. H. Angew. Chem. 1993, 105, 1181; Angew. Chem., Int. Ed. Engl. 1993, 105, 1130. Cohen, P. Nature 1982, 296, 613.
    • (1982) Nature , vol.296 , pp. 613
    • Cohen, P.1
  • 7
    • 0004210231 scopus 로고
    • Jones and Bartlett: Boston
    • Cooper, G. M. Oncogenes, 2nd ed., Jones and Bartlett: Boston 1995. Levitzki, A.; Gazit, A. Science 1995, 267, 1782.
    • (1995) Oncogenes, 2nd Ed.
    • Cooper, G.M.1
  • 8
    • 0028968949 scopus 로고
    • Cooper, G. M. Oncogenes, 2nd ed., Jones and Bartlett: Boston 1995. Levitzki, A.; Gazit, A. Science 1995, 267, 1782.
    • (1995) Science , vol.267 , pp. 1782
    • Levitzki, A.1    Gazit, A.2
  • 12
    • 0028337397 scopus 로고
    • For applications of phosphopeptides in biological studies see for instance: Eck, M. J.; Atwell, S. K.; Shoelson, S. E.; Harrison, S. C. Nature 1994, 368, 764. Tagawa, T.; Kuroki, T.; Vogt, P. K.; Chida, K. J. Cell. Biol. 1995, 130, 255. Perich, J. W.; Meggio, F.; Pinna, L. A. Bioorg. Med. Chem. 1996, 4, 143. Arnold, S.; Notides, A. C. Proc. Natl. Acad. Sci. USA 1995, 92, 7475. Waksman, G.; Shoelson, S. E.; Pant, N.; Cowborn, D.; Kuriyan, J. Cell 1993, 72, 779. Stone, R. L.; Dixon, J. E. J. Biol. Chem. 1994, 269, 31323.
    • (1994) Nature , vol.368 , pp. 764
    • Eck, M.J.1    Atwell, S.K.2    Shoelson, S.E.3    Harrison, S.C.4
  • 13
    • 0029009479 scopus 로고
    • For applications of phosphopeptides in biological studies see for instance: Eck, M. J.; Atwell, S. K.; Shoelson, S. E.; Harrison, S. C. Nature 1994, 368, 764. Tagawa, T.; Kuroki, T.; Vogt, P. K.; Chida, K. J. Cell. Biol. 1995, 130, 255. Perich, J. W.; Meggio, F.; Pinna, L. A. Bioorg. Med. Chem. 1996, 4, 143. Arnold, S.; Notides, A. C. Proc. Natl. Acad. Sci. USA 1995, 92, 7475. Waksman, G.; Shoelson, S. E.; Pant, N.; Cowborn, D.; Kuriyan, J. Cell 1993, 72, 779. Stone, R. L.; Dixon, J. E. J. Biol. Chem. 1994, 269, 31323.
    • (1995) J. Cell. Biol. , vol.130 , pp. 255
    • Tagawa, T.1    Kuroki, T.2    Vogt, P.K.3    Chida, K.4
  • 14
    • 0030004818 scopus 로고    scopus 로고
    • For applications of phosphopeptides in biological studies see for instance: Eck, M. J.; Atwell, S. K.; Shoelson, S. E.; Harrison, S. C. Nature 1994, 368, 764. Tagawa, T.; Kuroki, T.; Vogt, P. K.; Chida, K. J. Cell. Biol. 1995, 130, 255. Perich, J. W.; Meggio, F.; Pinna, L. A. Bioorg. Med. Chem. 1996, 4, 143. Arnold, S.; Notides, A. C. Proc. Natl. Acad. Sci. USA 1995, 92, 7475. Waksman, G.; Shoelson, S. E.; Pant, N.; Cowborn, D.; Kuriyan, J. Cell 1993, 72, 779. Stone, R. L.; Dixon, J. E. J. Biol. Chem. 1994, 269, 31323.
    • (1996) Bioorg. Med. Chem. , vol.4 , pp. 143
    • Perich, J.W.1    Meggio, F.2    Pinna, L.A.3
  • 15
    • 0029120606 scopus 로고
    • For applications of phosphopeptides in biological studies see for instance: Eck, M. J.; Atwell, S. K.; Shoelson, S. E.; Harrison, S. C. Nature 1994, 368, 764. Tagawa, T.; Kuroki, T.; Vogt, P. K.; Chida, K. J. Cell. Biol. 1995, 130, 255. Perich, J. W.; Meggio, F.; Pinna, L. A. Bioorg. Med. Chem. 1996, 4, 143. Arnold, S.; Notides, A. C. Proc. Natl. Acad. Sci. USA 1995, 92, 7475. Waksman, G.; Shoelson, S. E.; Pant, N.; Cowborn, D.; Kuriyan, J. Cell 1993, 72, 779. Stone, R. L.; Dixon, J. E. J. Biol. Chem. 1994, 269, 31323.
    • (1995) Proc. Natl. Acad. Sci. USA , vol.92 , pp. 7475
    • Arnold, S.1    Notides, A.C.2
  • 16
    • 0027409064 scopus 로고
    • For applications of phosphopeptides in biological studies see for instance: Eck, M. J.; Atwell, S. K.; Shoelson, S. E.; Harrison, S. C. Nature 1994, 368, 764. Tagawa, T.; Kuroki, T.; Vogt, P. K.; Chida, K. J. Cell. Biol. 1995, 130, 255. Perich, J. W.; Meggio, F.; Pinna, L. A. Bioorg. Med. Chem. 1996, 4, 143. Arnold, S.; Notides, A. C. Proc. Natl. Acad. Sci. USA 1995, 92, 7475. Waksman, G.; Shoelson, S. E.; Pant, N.; Cowborn, D.; Kuriyan, J. Cell 1993, 72, 779. Stone, R. L.; Dixon, J. E. J. Biol. Chem. 1994, 269, 31323.
    • (1993) Cell , vol.72 , pp. 779
    • Waksman, G.1    Shoelson, S.E.2    Pant, N.3    Cowborn, D.4    Kuriyan, J.5
  • 17
    • 0027970874 scopus 로고
    • For applications of phosphopeptides in biological studies see for instance: Eck, M. J.; Atwell, S. K.; Shoelson, S. E.; Harrison, S. C. Nature 1994, 368, 764. Tagawa, T.; Kuroki, T.; Vogt, P. K.; Chida, K. J. Cell. Biol. 1995, 130, 255. Perich, J. W.; Meggio, F.; Pinna, L. A. Bioorg. Med. Chem. 1996, 4, 143. Arnold, S.; Notides, A. C. Proc. Natl. Acad. Sci. USA 1995, 92, 7475. Waksman, G.; Shoelson, S. E.; Pant, N.; Cowborn, D.; Kuriyan, J. Cell 1993, 72, 779. Stone, R. L.; Dixon, J. E. J. Biol. Chem. 1994, 269, 31323.
    • (1994) J. Biol. Chem. , vol.269 , pp. 31323
    • Stone, R.L.1    Dixon, J.E.2
  • 19
    • 0000634675 scopus 로고
    • Wakamiya, T.; Saruta, K.; Yasuoka, Y.; Kusumoto, S. Chem. Lett. 1994, 1099. Wakamiya, T.; Togashi, R.; Nishida, T.; Saruta, K.; Yasuoka, J.; Kusumoto, S.; Aimoto, S.; Yoshizawa, K.; Kumagaye, S.; Nakajima, K.; Nagata, K. Bioorg. Med. Chem. 1996, 5, 135.
    • (1994) Chem. Lett. , pp. 1099
    • Wakamiya, T.1    Saruta, K.2    Yasuoka, Y.3    Kusumoto, S.4
  • 22
    • 0000634675 scopus 로고
    • The problem of β-elimination has alternatively been approached by using partially protected building blocks: Wakamiya, T.; Saruta, K.; Yasuoka, J.; Kusumoto, S. Chem. Lett. 1994, 1099. Bannwarth, W. Bioorg. Med. Chem. Lett. 1995, 5, 2661.
    • (1994) Chem. Lett. , pp. 1099
    • Wakamiya, T.1    Saruta, K.2    Yasuoka, J.3    Kusumoto, S.4
  • 23
    • 0028886074 scopus 로고
    • The problem of β-elimination has alternatively been approached by using partially protected building blocks: Wakamiya, T.; Saruta, K.; Yasuoka, J.; Kusumoto, S. Chem. Lett. 1994, 1099. Bannwarth, W. Bioorg. Med. Chem. Lett. 1995, 5, 2661.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 2661
    • Bannwarth, W.1
  • 24
    • 0001115594 scopus 로고    scopus 로고
    • Waldmann, H.; Schelhaas, M. Angew. Chem. 1996, 108, 2192; Angew. Chem., Int. Ed. Engl. 1996, 35, 2056. Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911.
    • (1996) Angew. Chem. , vol.108 , pp. 2192
    • Waldmann, H.1    Schelhaas, M.2
  • 25
    • 0029799743 scopus 로고    scopus 로고
    • Waldmann, H.; Schelhaas, M. Angew. Chem. 1996, 108, 2192; Angew. Chem., Int. Ed. Engl. 1996, 35, 2056. Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2056
  • 26
    • 0000680497 scopus 로고
    • Waldmann, H.; Schelhaas, M. Angew. Chem. 1996, 108, 2192; Angew. Chem., Int. Ed. Engl. 1996, 35, 2056. Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911.
    • (1994) Chem. Rev. , vol.94 , pp. 911
    • Waldmann, H.1    Sebastian, D.2
  • 27
    • 0001161423 scopus 로고
    • Waldmann, H.; Nagele, E. Angew. Chem. 1995, 107, 2425; Angew. Chem., Int. Ed. Engl. 1995, 34, 2259. Schelhaas, M.; Glomsda, S.; Hänsler, M.; Jakubke, H.-D.; Waldmann, H. Angew. Chem. 1996, 108, 82; Angew. Chem., Int. Ed. Engl. 1996, 35, 106. Pohl, T.; Waldmann, H. Angew. Chem. 1996, 108, 1829; Angew. Chem., Int. Ed. Engl. 1996, 35, 1720. Pohl, T.; Waldmann, H. J. Am. Chem. Soc. in press. Braun, P.; Waldmann, H.; Kunz, H. Bioorg. Med. Chem. 1993, 1, 197.
    • (1995) Angew. Chem. , vol.107 , pp. 2425
    • Waldmann, H.1    Nagele, E.2
  • 28
    • 0028887941 scopus 로고
    • Waldmann, H.; Nagele, E. Angew. Chem. 1995, 107, 2425; Angew. Chem., Int. Ed. Engl. 1995, 34, 2259. Schelhaas, M.; Glomsda, S.; Hänsler, M.; Jakubke, H.-D.; Waldmann, H. Angew. Chem. 1996, 108, 82; Angew. Chem., Int. Ed. Engl. 1996, 35, 106. Pohl, T.; Waldmann, H. Angew. Chem. 1996, 108, 1829; Angew. Chem., Int. Ed. Engl. 1996, 35, 1720. Pohl, T.; Waldmann, H. J. Am. Chem. Soc. in press. Braun, P.; Waldmann, H.; Kunz, H. Bioorg. Med. Chem. 1993, 1, 197.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 2259
  • 29
    • 0002916147 scopus 로고    scopus 로고
    • Waldmann, H.; Nagele, E. Angew. Chem. 1995, 107, 2425; Angew. Chem., Int. Ed. Engl. 1995, 34, 2259. Schelhaas, M.; Glomsda, S.; Hänsler, M.; Jakubke, H.-D.; Waldmann, H. Angew. Chem. 1996, 108, 82; Angew. Chem., Int. Ed. Engl. 1996, 35, 106. Pohl, T.; Waldmann, H. Angew. Chem. 1996, 108, 1829; Angew. Chem., Int. Ed. Engl. 1996, 35, 1720. Pohl, T.; Waldmann, H. J. Am. Chem. Soc. in press. Braun, P.; Waldmann, H.; Kunz, H. Bioorg. Med. Chem. 1993, 1, 197.
    • (1996) Angew. Chem. , vol.108 , pp. 82
    • Schelhaas, M.1    Glomsda, S.2    Hänsler, M.3    Jakubke, H.-D.4    Waldmann, H.5
  • 30
    • 0030056960 scopus 로고    scopus 로고
    • Waldmann, H.; Nagele, E. Angew. Chem. 1995, 107, 2425; Angew. Chem., Int. Ed. Engl. 1995, 34, 2259. Schelhaas, M.; Glomsda, S.; Hänsler, M.; Jakubke, H.-D.; Waldmann, H. Angew. Chem. 1996, 108, 82; Angew. Chem., Int. Ed. Engl. 1996, 35, 106. Pohl, T.; Waldmann, H. Angew. Chem. 1996, 108, 1829; Angew. Chem., Int. Ed. Engl. 1996, 35, 1720. Pohl, T.; Waldmann, H. J. Am. Chem. Soc. in press. Braun, P.; Waldmann, H.; Kunz, H. Bioorg. Med. Chem. 1993, 1, 197.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 106
  • 31
    • 0000467380 scopus 로고    scopus 로고
    • Waldmann, H.; Nagele, E. Angew. Chem. 1995, 107, 2425; Angew. Chem., Int. Ed. Engl. 1995, 34, 2259. Schelhaas, M.; Glomsda, S.; Hänsler, M.; Jakubke, H.-D.; Waldmann, H. Angew. Chem. 1996, 108, 82; Angew. Chem., Int. Ed. Engl. 1996, 35, 106. Pohl, T.; Waldmann, H. Angew. Chem. 1996, 108, 1829; Angew. Chem., Int. Ed. Engl. 1996, 35, 1720. Pohl, T.; Waldmann, H. J. Am. Chem. Soc. in press. Braun, P.; Waldmann, H.; Kunz, H. Bioorg. Med. Chem. 1993, 1, 197.
    • (1996) Angew. Chem. , vol.108 , pp. 1829
    • Pohl, T.1    Waldmann, H.2
  • 32
    • 0029778803 scopus 로고    scopus 로고
    • Waldmann, H.; Nagele, E. Angew. Chem. 1995, 107, 2425; Angew. Chem., Int. Ed. Engl. 1995, 34, 2259. Schelhaas, M.; Glomsda, S.; Hänsler, M.; Jakubke, H.-D.; Waldmann, H. Angew. Chem. 1996, 108, 82; Angew. Chem., Int. Ed. Engl. 1996, 35, 106. Pohl, T.; Waldmann, H. Angew. Chem. 1996, 108, 1829; Angew. Chem., Int. Ed. Engl. 1996, 35, 1720. Pohl, T.; Waldmann, H. J. Am. Chem. Soc. in press. Braun, P.; Waldmann, H.; Kunz, H. Bioorg. Med. Chem. 1993, 1, 197.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1720
  • 33
    • 84889551313 scopus 로고    scopus 로고
    • in press
    • Waldmann, H.; Nagele, E. Angew. Chem. 1995, 107, 2425; Angew. Chem., Int. Ed. Engl. 1995, 34, 2259. Schelhaas, M.; Glomsda, S.; Hänsler, M.; Jakubke, H.-D.; Waldmann, H. Angew. Chem. 1996, 108, 82; Angew. Chem., Int. Ed. Engl. 1996, 35, 106. Pohl, T.; Waldmann, H. Angew. Chem. 1996, 108, 1829; Angew. Chem., Int. Ed. Engl. 1996, 35, 1720. Pohl, T.; Waldmann, H. J. Am. Chem. Soc. in press. Braun, P.; Waldmann, H.; Kunz, H. Bioorg. Med. Chem. 1993, 1, 197.
    • J. Am. Chem. Soc.
    • Pohl, T.1    Waldmann, H.2
  • 34
    • 0027662411 scopus 로고
    • Waldmann, H.; Nagele, E. Angew. Chem. 1995, 107, 2425; Angew. Chem., Int. Ed. Engl. 1995, 34, 2259. Schelhaas, M.; Glomsda, S.; Hänsler, M.; Jakubke, H.-D.; Waldmann, H. Angew. Chem. 1996, 108, 82; Angew. Chem., Int. Ed. Engl. 1996, 35, 106. Pohl, T.; Waldmann, H. Angew. Chem. 1996, 108, 1829; Angew. Chem., Int. Ed. Engl. 1996, 35, 1720. Pohl, T.; Waldmann, H. J. Am. Chem. Soc. in press. Braun, P.; Waldmann, H.; Kunz, H. Bioorg. Med. Chem. 1993, 1, 197.
    • (1993) Bioorg. Med. Chem. , vol.1 , pp. 197
    • Braun, P.1    Waldmann, H.2    Kunz, H.3
  • 35
    • 0030602202 scopus 로고    scopus 로고
    • For preliminary communications of part of this work see: Heuser, A.; Schulze, S.; Waldmann, H. Tetrahedron Lett. 1996, 37, 8725. Sebastian, D.; Waldmann, H. Tetrahedron Lett. 1997, 38, 2927.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 8725
    • Heuser, A.1    Schulze, S.2    Waldmann, H.3
  • 36
    • 0030963407 scopus 로고    scopus 로고
    • For preliminary communications of part of this work see: Heuser, A.; Schulze, S.; Waldmann, H. Tetrahedron Lett. 1996, 37, 8725. Sebastian, D.; Waldmann, H. Tetrahedron Lett. 1997, 38, 2927.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 2927
    • Sebastian, D.1    Waldmann, H.2
  • 39
    • 84889524105 scopus 로고    scopus 로고
    • note
    • The unphosphorylated peptides were built up according to well established procedures of peptide chemistry described in refs (14) and (15).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.