메뉴 건너뛰기




Volumn 313, Issue 2, 1998, Pages 107-116

Synthesis of an N-glucoasparagine analog as a building block for a V3-loop glycopeptide from GP120 of HIV-I

Author keywords

Carbohydrates; Glycopeptides; HIV; Mimetics; Solid phase synthesis

Indexed keywords

ASPARAGINE DERIVATIVE; GLYCOPEPTIDE; N4 (3,4,6 TRI O ACETYL 1,5 ANHYDRO 2 DEOXYGLUCITOL)ASPARAGINE; UNCLASSIFIED DRUG;

EID: 0032413195     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(98)00252-3     Document Type: Article
Times cited : (7)

References (39)
  • 3
    • 0030002637 scopus 로고    scopus 로고
    • G. Alkhatib C. Combadiere, C.C. Broder, Y. Feng, P.E. Kennedy, P.M. Murphy, and E.A. Berger, Science, 272 (1996) 1955-1958; Y. Feng, C.C. Broder, P.E. Kennedy, and E.A. Berger, Science, 272 (1996) 872-877.
    • (1996) Science , vol.272 , pp. 872-877
    • Feng, Y.1    Broder, C.C.2    Kennedy, P.E.3    Berger, E.A.4
  • 6
    • 0027379922 scopus 로고
    • P.N. Nehete, R.B. Arlinghaus, and K.J. Sastry, J. Virol., 67 (1993) 6841-6846; N. Yahi, J Fantini, S. Baghdiguian, K. Mabrouk, C. Tamalet, H. Rochat, J van Rietschoten, and J.M. Sabatier, Proc. Natl. Acad. Sci. USA, 92 (1995) 4867-4871.
    • (1993) J. Virol. , vol.67 , pp. 6841-6846
    • Nehete, P.N.1    Arlinghaus, R.B.2    Sastry, K.J.3
  • 10
    • 0027741165 scopus 로고
    • J. Fantini, N. Yahi, K. Mabrouk, J. Van Rietschoten, H. Rochat, and J.M. Sabatier, C. R. Acad. Sci. III, 316 (1993) 1381-1387; N. Yahi, J. Fantini, K. Mabrouk, C. Tamalet, P. de Micco, J. van Rietschoten, H. Rochat, and J.M. Sabatier, J. Virol., 68(9) (1994) 5714-5720; N. Yahi, J.M. Sabatier, S. Baghdiguian, F. Gonzalez-Scarano, and J. Fantini, J. Virol., 69 (1995) 320-325.
    • (1993) C. R. Acad. Sci. III , vol.316 , pp. 1381-1387
    • Fantini, J.1    Yahi, N.2    Mabrouk, K.3    Van Rietschoten, J.4    Rochat, H.5    Sabatier, J.M.6
  • 11
    • 0028001217 scopus 로고
    • J. Fantini, N. Yahi, K. Mabrouk, J. Van Rietschoten, H. Rochat, and J.M. Sabatier, C. R. Acad. Sci. III, 316 (1993) 1381-1387; N. Yahi, J. Fantini, K. Mabrouk, C. Tamalet, P. de Micco, J. van Rietschoten, H. Rochat, and J.M. Sabatier, J. Virol., 68(9) (1994) 5714-5720; N. Yahi, J.M. Sabatier, S. Baghdiguian, F. Gonzalez-Scarano, and J. Fantini, J. Virol., 69 (1995) 320-325.
    • (1994) J. Virol. , vol.68 , Issue.9 , pp. 5714-5720
    • Yahi, N.1    Fantini, J.2    Mabrouk, K.3    Tamalet, C.4    De Micco, P.5    Van Rietschoten, J.6    Rochat, H.7    Sabatier, J.M.8
  • 12
    • 0028936189 scopus 로고
    • J. Fantini, N. Yahi, K. Mabrouk, J. Van Rietschoten, H. Rochat, and J.M. Sabatier, C. R. Acad. Sci. III, 316 (1993) 1381-1387; N. Yahi, J. Fantini, K. Mabrouk, C. Tamalet, P. de Micco, J. van Rietschoten, H. Rochat, and J.M. Sabatier, J. Virol., 68(9) (1994) 5714-5720; N. Yahi, J.M. Sabatier, S. Baghdiguian, F. Gonzalez-Scarano, and J. Fantini, J. Virol., 69 (1995) 320-325.
    • (1995) J. Virol. , vol.69 , pp. 320-325
    • Yahi, N.1    Sabatier, J.M.2    Baghdiguian, S.3    Gonzalez-Scarano, F.4    Fantini, J.5
  • 16
    • 0030789620 scopus 로고    scopus 로고
    • F. Burkhardt, M. Hoffmann, and H. Kessler, Angew. Chem. Int. Ed. Engl., 36 (1997) 1191-1192; C.R. Bertozzi, P.D. Hoeprich Jr., and M.D. Bednarski, J. Org. Chem., 57 (1992) 6092-6094; J. Hofsteenge, D.R. Müller, T. de Beer, A. Löffler, W.J. Richter, and J.F.G. Vliegenthart, Biochemistry, 33 (1994) 13524-13530; A. Chenede, E. Perrin, E.D. Rekai, and P. Sinay, Synlett, 6 (1994) 420-425; S.C.T. Svensson, and J. Thiem, Carbohydr. Res., 200 (1990) 391-402; T. Haneda, P.G. Goekjian, S.H. Kim, and Y. Kishi, J. Org. Chem., 57 (1992) 490-498; G. Simchen, and E. Pürkner, Synthesis, (1990) 525-527; L.-X. Wang, J-Q. Fan, and Y.C. Lee, Tetrahedron Lett., 37 (1996) 1975-1978; R. Preuss, and R.R. Schmidt, Chemical synthesis of glycopeptides, J. Carbohydr. Chem., 10 (1991) 887-900.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 1191-1192
    • Burkhardt, F.1    Hoffmann, M.2    Kessler, H.3
  • 17
    • 0026743454 scopus 로고
    • F. Burkhardt, M. Hoffmann, and H. Kessler, Angew. Chem. Int. Ed. Engl., 36 (1997) 1191-1192; C.R. Bertozzi, P.D. Hoeprich Jr., and M.D. Bednarski, J. Org. Chem., 57 (1992) 6092-6094; J. Hofsteenge, D.R. Müller, T. de Beer, A. Löffler, W.J. Richter, and J.F.G. Vliegenthart, Biochemistry, 33 (1994) 13524-13530; A. Chenede, E. Perrin, E.D. Rekai, and P. Sinay, Synlett, 6 (1994) 420-425; S.C.T. Svensson, and J. Thiem, Carbohydr. Res., 200 (1990) 391-402; T. Haneda, P.G. Goekjian, S.H. Kim, and Y. Kishi, J. Org. Chem., 57 (1992) 490-498; G. Simchen, and E. Pürkner, Synthesis, (1990) 525-527; L.-X. Wang, J-Q. Fan, and Y.C. Lee, Tetrahedron Lett., 37 (1996) 1975-1978; R. Preuss, and R.R. Schmidt, Chemical synthesis of glycopeptides, J. Carbohydr. Chem., 10 (1991) 887-900.
    • (1992) J. Org. Chem. , vol.57 , pp. 6092-6094
    • Bertozzi, C.R.1    Hoeprich Jr., P.D.2    Bednarski, M.D.3
  • 18
    • 0028033725 scopus 로고
    • F. Burkhardt, M. Hoffmann, and H. Kessler, Angew. Chem. Int. Ed. Engl., 36 (1997) 1191-1192; C.R. Bertozzi, P.D. Hoeprich Jr., and M.D. Bednarski, J. Org. Chem., 57 (1992) 6092-6094; J. Hofsteenge, D.R. Müller, T. de Beer, A. Löffler, W.J. Richter, and J.F.G. Vliegenthart, Biochemistry, 33 (1994) 13524-13530; A. Chenede, E. Perrin, E.D. Rekai, and P. Sinay, Synlett, 6 (1994) 420-425; S.C.T. Svensson, and J. Thiem, Carbohydr. Res., 200 (1990) 391-402; T. Haneda, P.G. Goekjian, S.H. Kim, and Y. Kishi, J. Org. Chem., 57 (1992) 490-498; G. Simchen, and E. Pürkner, Synthesis, (1990) 525-527; L.-X. Wang, J-Q. Fan, and Y.C. Lee, Tetrahedron Lett., 37 (1996) 1975-1978; R. Preuss, and R.R. Schmidt, Chemical synthesis of glycopeptides, J. Carbohydr. Chem., 10 (1991) 887-900.
    • (1994) Biochemistry , vol.33 , pp. 13524-13530
    • Hofsteenge, J.1    Müller, D.R.2    De Beer, T.3    Löffler, A.4    Richter, W.J.5    Vliegenthart, J.F.G.6
  • 19
    • 85064651982 scopus 로고
    • F. Burkhardt, M. Hoffmann, and H. Kessler, Angew. Chem. Int. Ed. Engl., 36 (1997) 1191-1192; C.R. Bertozzi, P.D. Hoeprich Jr., and M.D. Bednarski, J. Org. Chem., 57 (1992) 6092-6094; J. Hofsteenge, D.R. Müller, T. de Beer, A. Löffler, W.J. Richter, and J.F.G. Vliegenthart, Biochemistry, 33 (1994) 13524-13530; A. Chenede, E. Perrin, E.D. Rekai, and P. Sinay, Synlett, 6 (1994) 420-425; S.C.T. Svensson, and J. Thiem, Carbohydr. Res., 200 (1990) 391-402; T. Haneda, P.G. Goekjian, S.H. Kim, and Y. Kishi, J. Org. Chem., 57 (1992) 490-498; G. Simchen, and E. Pürkner, Synthesis, (1990) 525-527; L.-X. Wang, J-Q. Fan, and Y.C. Lee, Tetrahedron Lett., 37 (1996) 1975-1978; R. Preuss, and R.R. Schmidt, Chemical synthesis of glycopeptides, J. Carbohydr. Chem., 10 (1991) 887-900.
    • (1994) Synlett , vol.6 , pp. 420-425
    • Chenede, A.1    Perrin, E.2    Rekai, E.D.3    Sinay, P.4
  • 20
    • 0025714081 scopus 로고
    • F. Burkhardt, M. Hoffmann, and H. Kessler, Angew. Chem. Int. Ed. Engl., 36 (1997) 1191-1192; C.R. Bertozzi, P.D. Hoeprich Jr., and M.D. Bednarski, J. Org. Chem., 57 (1992) 6092-6094; J. Hofsteenge, D.R. Müller, T. de Beer, A. Löffler, W.J. Richter, and J.F.G. Vliegenthart, Biochemistry, 33 (1994) 13524-13530; A. Chenede, E. Perrin, E.D. Rekai, and P. Sinay, Synlett, 6 (1994) 420-425; S.C.T. Svensson, and J. Thiem, Carbohydr. Res., 200 (1990) 391-402; T. Haneda, P.G. Goekjian, S.H. Kim, and Y. Kishi, J. Org. Chem., 57 (1992) 490-498; G. Simchen, and E. Pürkner, Synthesis, (1990) 525-527; L.-X. Wang, J-Q. Fan, and Y.C. Lee, Tetrahedron Lett., 37 (1996) 1975-1978; R. Preuss, and R.R. Schmidt, Chemical synthesis of glycopeptides, J. Carbohydr. Chem., 10 (1991) 887-900.
    • (1990) Carbohydr. Res. , vol.200 , pp. 391-402
    • Svensson, S.C.T.1    Thiem, J.2
  • 21
    • 0001712471 scopus 로고
    • F. Burkhardt, M. Hoffmann, and H. Kessler, Angew. Chem. Int. Ed. Engl., 36 (1997) 1191-1192; C.R. Bertozzi, P.D. Hoeprich Jr., and M.D. Bednarski, J. Org. Chem., 57 (1992) 6092-6094; J. Hofsteenge, D.R. Müller, T. de Beer, A. Löffler, W.J. Richter, and J.F.G. Vliegenthart, Biochemistry, 33 (1994) 13524-13530; A. Chenede, E. Perrin, E.D. Rekai, and P. Sinay, Synlett, 6 (1994) 420-425; S.C.T. Svensson, and J. Thiem, Carbohydr. Res., 200 (1990) 391-402; T. Haneda, P.G. Goekjian, S.H. Kim, and Y. Kishi, J. Org. Chem., 57 (1992) 490-498; G. Simchen, and E. Pürkner, Synthesis, (1990) 525-527; L.-X. Wang, J-Q. Fan, and Y.C. Lee, Tetrahedron Lett., 37 (1996) 1975-1978; R. Preuss, and R.R. Schmidt, Chemical synthesis of glycopeptides, J. Carbohydr. Chem., 10 (1991) 887-900.
    • (1992) J. Org. Chem. , vol.57 , pp. 490-498
    • Haneda, T.1    Goekjian, P.G.2    Kim, S.H.3    Kishi, Y.4
  • 22
    • 0025299720 scopus 로고
    • F. Burkhardt, M. Hoffmann, and H. Kessler, Angew. Chem. Int. Ed. Engl., 36 (1997) 1191-1192; C.R. Bertozzi, P.D. Hoeprich Jr., and M.D. Bednarski, J. Org. Chem., 57 (1992) 6092-6094; J. Hofsteenge, D.R. Müller, T. de Beer, A. Löffler, W.J. Richter, and J.F.G. Vliegenthart, Biochemistry, 33 (1994) 13524-13530; A. Chenede, E. Perrin, E.D. Rekai, and P. Sinay, Synlett, 6 (1994) 420-425; S.C.T. Svensson, and J. Thiem, Carbohydr. Res., 200 (1990) 391-402; T. Haneda, P.G. Goekjian, S.H. Kim, and Y. Kishi, J. Org. Chem., 57 (1992) 490-498; G. Simchen, and E. Pürkner, Synthesis, (1990) 525-527; L.-X. Wang, J-Q. Fan, and Y.C. Lee, Tetrahedron Lett., 37 (1996) 1975-1978; R. Preuss, and R.R. Schmidt, Chemical synthesis of glycopeptides, J. Carbohydr. Chem., 10 (1991) 887-900.
    • (1990) Synthesis , pp. 525-527
    • Simchen, G.1    Pürkner, E.2
  • 23
    • 0029914514 scopus 로고    scopus 로고
    • F. Burkhardt, M. Hoffmann, and H. Kessler, Angew. Chem. Int. Ed. Engl., 36 (1997) 1191-1192; C.R. Bertozzi, P.D. Hoeprich Jr., and M.D. Bednarski, J. Org. Chem., 57 (1992) 6092-6094; J. Hofsteenge, D.R. Müller, T. de Beer, A. Löffler, W.J. Richter, and J.F.G. Vliegenthart, Biochemistry, 33 (1994) 13524-13530; A. Chenede, E. Perrin, E.D. Rekai, and P. Sinay, Synlett, 6 (1994) 420-425; S.C.T. Svensson, and J. Thiem, Carbohydr. Res., 200 (1990) 391-402; T. Haneda, P.G. Goekjian, S.H. Kim, and Y. Kishi, J. Org. Chem., 57 (1992) 490-498; G. Simchen, and E. Pürkner, Synthesis, (1990) 525-527; L.-X. Wang, J-Q. Fan, and Y.C. Lee, Tetrahedron Lett., 37 (1996) 1975-1978; R. Preuss, and R.R. Schmidt, Chemical synthesis of glycopeptides, J. Carbohydr. Chem., 10 (1991) 887-900.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1975-1978
    • Wang, L.-X.1    Fan, J.-Q.2    Lee, Y.C.3
  • 24
    • 0001664904 scopus 로고
    • Chemical synthesis of glycopeptides
    • F. Burkhardt, M. Hoffmann, and H. Kessler, Angew. Chem. Int. Ed. Engl., 36 (1997) 1191-1192; C.R. Bertozzi, P.D. Hoeprich Jr., and M.D. Bednarski, J. Org. Chem., 57 (1992) 6092-6094; J. Hofsteenge, D.R. Müller, T. de Beer, A. Löffler, W.J. Richter, and J.F.G. Vliegenthart, Biochemistry, 33 (1994) 13524-13530; A. Chenede, E. Perrin, E.D. Rekai, and P. Sinay, Synlett, 6 (1994) 420-425; S.C.T. Svensson, and J. Thiem, Carbohydr. Res., 200 (1990) 391-402; T. Haneda, P.G. Goekjian, S.H. Kim, and Y. Kishi, J. Org. Chem., 57 (1992) 490-498; G. Simchen, and E. Pürkner, Synthesis, (1990) 525-527; L.-X. Wang, J-Q. Fan, and Y.C. Lee, Tetrahedron Lett., 37 (1996) 1975-1978; R. Preuss, and R.R. Schmidt, Chemical synthesis of glycopeptides, J. Carbohydr. Chem., 10 (1991) 887-900.
    • (1991) J. Carbohydr. Chem. , vol.10 , pp. 887-900
    • Preuss, R.1    Schmidt, R.R.2
  • 25
    • 0002422576 scopus 로고
    • J. Montreuil, JF.G. Vliegenthart, H. Schachter (Eds.), Elsevier, Amsterdam
    • H. Paulsen, S. Peters, T. Bielfeldt, in J. Montreuil, JF.G. Vliegenthart, H. Schachter (Eds.), Glycoproteins, Elsevier, Amsterdam, 1995, pp. 87-122.
    • (1995) Glycoproteins , pp. 87-122
    • Paulsen, H.1    Peters, S.2    Bielfeldt, T.3
  • 29
    • 0000341931 scopus 로고
    • B.F. Cain, J. Org. Chem., 41 (1976) 2029-2031; S. Hanessian, Methods Carbohydr. Chem. 6 (1972) 209-214.
    • (1976) J. Org. Chem. , vol.41 , pp. 2029-2031
    • Cain, B.F.1
  • 31
    • 13044282703 scopus 로고    scopus 로고
    • note
    • 7 was obtained from L-Asp(OH)-OBn and Z-Cl using standard procedures.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.