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Volumn , Issue 11, 1998, Pages 2437-2449

Synthesis of combinatorial libraries of vinylogous sulfonamidopeptides (vs-peptides)

Author keywords

Combinatorial libraries; Michael addition; N Alkylation; Solid phase synthesis; Vinylogous sulfonamidopeptides

Indexed keywords


EID: 0003065437     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199811)1998:11<2437::aid-ejoc2437>3.0.co;2-8     Document Type: Article
Times cited : (24)

References (101)
  • 6
    • 0542421525 scopus 로고    scopus 로고
    • [3a] For recent reviews, see: S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180; R. M. J. Liskamp, Angew. Chem. 1994, 106, 661-664, Angew. Chem. Int. Ed. Engl. 1994, 33, 633-636, S. Borman, Chem. Eng. News 1997, June 16, 32-35.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 173-180
    • Gellman, S.H.1
  • 7
    • 0042953146 scopus 로고
    • [3a] For recent reviews, see: S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180; R. M. J. Liskamp, Angew. Chem. 1994, 106, 661-664, Angew. Chem. Int. Ed. Engl. 1994, 33, 633-636, S. Borman, Chem. Eng. News 1997, June 16, 32-35.
    • (1994) Angew. Chem. , vol.106 , pp. 661-664
    • Liskamp, R.M.J.1
  • 8
    • 33748226252 scopus 로고
    • [3a] For recent reviews, see: S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180; R. M. J. Liskamp, Angew. Chem. 1994, 106, 661-664, Angew. Chem. Int. Ed. Engl. 1994, 33, 633-636, S. Borman, Chem. Eng. News 1997, June 16, 32-35.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 633-636
  • 9
    • 84888121021 scopus 로고    scopus 로고
    • June 16
    • [3a] For recent reviews, see: S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180; R. M. J. Liskamp, Angew. Chem. 1994, 106, 661-664, Angew. Chem. Int. Ed. Engl. 1994, 33, 633-636, S. Borman, Chem. Eng. News 1997, June 16, 32-35.
    • (1997) Chem. Eng. News , pp. 32-35
    • Borman, S.1
  • 15
    • 0000517240 scopus 로고
    • [3f] K. Burgess, D. S. Linthicum, H. Shin, Angew. Chem. 1995, 107, 975, Angew. Chem. Int Ed. Engl 1995, 34, 907-909.
    • (1995) Angew. Chem. Int Ed. Engl , vol.34 , pp. 907-909
  • 23
    • 0002138857 scopus 로고    scopus 로고
    • [4a] J. S. Früchtel, G. Jung. Angew. Chem 1996, 108, 19-46, Angew. Chem Int Ed. Engl. 1996, 35, 17-42.
    • (1996) Angew. Chem , vol.108 , pp. 19-46
    • Früchtel, J.S.1    Jung, G.2
  • 24
    • 0003180602 scopus 로고    scopus 로고
    • [4a] J. S. Früchtel, G. Jung. Angew. Chem 1996, 108, 19-46, Angew. Chem Int Ed. Engl. 1996, 35, 17-42.
    • (1996) Angew. Chem Int Ed. Engl. , vol.35 , pp. 17-42
  • 26
    • 0030477258 scopus 로고    scopus 로고
    • [4b] F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436-2487, Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2288-2337
  • 29
    • 0000734566 scopus 로고
    • [5a] A. Giannis, T. Kolter, Angew. Chem. 1993, 105, 1303-1326; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267.
    • (1993) Angew. Chem. , vol.105 , pp. 1303-1326
    • Giannis, A.1    Kolter, T.2
  • 30
    • 33745502124 scopus 로고
    • [5a] A. Giannis, T. Kolter, Angew. Chem. 1993, 105, 1303-1326; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 1244-1267
  • 32
  • 33
    • 0030470056 scopus 로고    scopus 로고
    • For recent examples, see: [6a] D. P. Rotella, J. Am. Chem. Soc. 1996, 118, 12246-12247. [6b] P. Wipf, T. C. Henninger, J. Org. Chem. 1997, 62, 1586-1587, and references therein.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 12246-12247
    • Rotella, D.P.1
  • 34
    • 0030977733 scopus 로고    scopus 로고
    • and references therein
    • For recent examples, see: [6a] D. P. Rotella, J. Am. Chem. Soc. 1996, 118, 12246-12247. [6b] P. Wipf, T. C. Henninger, J. Org. Chem. 1997, 62, 1586-1587, and references therein.
    • (1997) J. Org. Chem. , vol.62 , pp. 1586-1587
    • Wipf, P.1    Henninger, T.C.2
  • 51
    • 2842536584 scopus 로고    scopus 로고
    • vsAA-OH = vinylogous sulfonyl amino acid. Defined vinylogous sulfonyl amino acid residues are described by the vs prefix to the three-letter code of the corresponding amino acid, e.g. vsAla = vinylogous sulfonyl alanyl
    • vsAA-OH = vinylogous sulfonyl amino acid. Defined vinylogous sulfonyl amino acid residues are described by the vs prefix to the three-letter code of the corresponding amino acid, e.g. vsAla = vinylogous sulfonyl alanyl.
  • 52
    • 0001327727 scopus 로고
    • [11a] For a preliminary communication on the synthesis of vs-peptides in solution, see: C. Gennari, B. Salom, D. Potenza, A. Williams, Angew. Chem. 1994, 106, 2181-2183, Angew: Chem. Int. Ed. Engl 1994, 33. 2067-2069.
    • (1994) Angew. Chem. , vol.106 , pp. 2181-2183
    • Gennari, C.1    Salom, B.2    Potenza, D.3    Williams, A.4
  • 53
    • 0000455904 scopus 로고
    • [11a] For a preliminary communication on the synthesis of vs-peptides in solution, see: C. Gennari, B. Salom, D. Potenza, A. Williams, Angew. Chem. 1994, 106, 2181-2183, Angew: Chem. Int. Ed. Engl 1994, 33. 2067-2069.
    • (1994) Angew: Chem. Int. Ed. Engl , vol.33 , pp. 2067-2069
  • 55
    • 2842519818 scopus 로고    scopus 로고
    • Italian Patent. Application 17 May 1994, N. MI94 A 000989
    • [11c] C.Gennari, B. Salom, D. Potenza, Italian Patent. Application 17 May 1994, N. MI94 A 000989; PCT Int. Appl. EP 95 - 01788, 11 May 1995; Chem. Abstr. 1996, 124, P 233152v.
    • Gennari, C.1    Salom, B.2    Potenza, D.3
  • 56
    • 2842551044 scopus 로고    scopus 로고
    • PCT Int. Appl. EP 95 - 01788, 11 May 1995
    • [11c] C.Gennari, B. Salom, D. Potenza, Italian Patent. Application 17 May 1994, N. MI94 A 000989; PCT Int. Appl. EP 95 - 01788, 11 May 1995; Chem. Abstr. 1996, 124, P 233152v.
  • 57
    • 25544470109 scopus 로고    scopus 로고
    • [11c] C.Gennari, B. Salom, D. Potenza, Italian Patent. Application 17 May 1994, N. MI94 A 000989; PCT Int. Appl. EP 95 - 01788, 11 May 1995; Chem. Abstr. 1996, 124, P 233152v.
    • (1996) Chem. Abstr. , vol.124
  • 59
    • 0001062772 scopus 로고
    • [11e] For molecular recognition studies using vs-peptides, see: C. Gennari, H. P. Nestler, B. Salom, W.C. Still, Angew. Chem. 1995, 107, 1894-1896, Angew. Chem Int. Ed. Engl. 1995, 34, 1765-1768.
    • (1995) Angew. Chem. , vol.107 , pp. 1894-1896
    • Gennari, C.1    Nestler, H.P.2    Salom, B.3    Still, W.C.4
  • 60
    • 33748831629 scopus 로고
    • [11e] For molecular recognition studies using vs-peptides, see: C. Gennari, H. P. Nestler, B. Salom, W.C. Still, Angew. Chem. 1995, 107, 1894-1896, Angew. Chem Int. Ed. Engl. 1995, 34, 1765-1768.
    • (1995) Angew. Chem Int. Ed. Engl. , vol.34 , pp. 1765-1768
  • 66
    • 0000990987 scopus 로고
    • For a preliminary communication on SPS of vs-peptides, see: C. Gennari, H. P. Nestler, B. Salom, W. C. Still, Angew. Chem 1995, 107, 1892-1893, Angew. Chem. Int. Ed. Engl. 1995, 34, 1763-1765.
    • (1995) Angew. Chem , vol.107 , pp. 1892-1893
    • Gennari, C.1    Nestler, H.P.2    Salom, B.3    Still, W.C.4
  • 67
    • 33748242808 scopus 로고
    • For a preliminary communication on SPS of vs-peptides, see: C. Gennari, H. P. Nestler, B. Salom, W. C. Still, Angew. Chem 1995, 107, 1892-1893, Angew. Chem. Int. Ed. Engl. 1995, 34, 1763-1765.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1763-1765
  • 68
    • 0039754147 scopus 로고    scopus 로고
    • For recent examples of sulfonamide N-alkylation, see: [14a] K Wisniewski, A. S. Kolodziejczyk, Tetrahedron Lett. 1997, 38, 483-486. [14b] S. M. Dankwardt, D. B. Smith, J. A. Porco, Jr., C. H. Nguyen, Synlett 1997, 854-856. [14c] C. Kay, P. J. Murray, L. Sandow, A. B. Holmes, Tetrahedron Lett. 1997, 38, 6941-6944. [14d] H. S. M. Lu, M. Volk, Y. Kholodenko, E. Gooding, R. M. Hochstrasser, W. F. DeGrado, J. Am. Chem. Soc. 1997, 119, 7173-7180. [14e] J. F. Reichwein, R. M. J. Liskamp, Tetrahedron Lett. 1998, 39, 1243-1246. [14f] G. L. Bolton, Tetrahedron Lett. 1996, 37, 3433-3436. [14g] B. J. Backes, A. A. Virgilio, J. A. Ellman, J. Am. Chem. Soc. 1996, 118, 3055-3056. [14h] S C. Miller, T. S. Scanlan, J. Am. Chem. Soc. 1997, 119, 2301-2302. - For recent examples of peptide N-alkylation, [14i] B. Dörner, G. M. Husar, J. M. Ostresh, R. A. Houghten, Biorg. Med. Chem. 1996, 4, 709-715. [14j] K. Ohmori, T. Okuno, S. Nishiyama, S. Yamamura, Tetrahedron Lett. 1996, 37, 3467-3470.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 483-486
    • Wisniewski, K.1    Kolodziejczyk, A.S.2
  • 69
    • 1542639596 scopus 로고    scopus 로고
    • For recent examples of sulfonamide N-alkylation, see: [14a] K Wisniewski, A. S. Kolodziejczyk, Tetrahedron Lett. 1997, 38, 483-486. [14b] S. M. Dankwardt, D. B. Smith, J. A. Porco, Jr., C. H. Nguyen, Synlett 1997, 854-856. [14c] C. Kay, P. J. Murray, L. Sandow, A. B. Holmes, Tetrahedron Lett. 1997, 38, 6941-6944. [14d] H. S. M. Lu, M. Volk, Y. Kholodenko, E. Gooding, R. M. Hochstrasser, W. F. DeGrado, J. Am. Chem. Soc. 1997, 119, 7173-7180. [14e] J. F. Reichwein, R. M. J. Liskamp, Tetrahedron Lett. 1998, 39, 1243-1246. [14f] G. L. Bolton, Tetrahedron Lett. 1996, 37, 3433-3436. [14g] B. J. Backes, A. A. Virgilio, J. A. Ellman, J. Am. Chem. Soc. 1996, 118, 3055-3056. [14h] S C. Miller, T. S. Scanlan, J. Am. Chem. Soc. 1997, 119, 2301-2302. - For recent examples of peptide N-alkylation, [14i] B. Dörner, G. M. Husar, J. M. Ostresh, R. A. Houghten, Biorg. Med. Chem. 1996, 4, 709-715. [14j] K. Ohmori, T. Okuno, S. Nishiyama, S. Yamamura, Tetrahedron Lett. 1996, 37, 3467-3470.
    • (1997) Synlett , pp. 854-856
    • Dankwardt, S.M.1    Smith, D.B.2    Porco Jr., J.A.3    Nguyen, C.H.4
  • 70
    • 0030813392 scopus 로고    scopus 로고
    • For recent examples of sulfonamide N-alkylation, see: [14a] K Wisniewski, A. S. Kolodziejczyk, Tetrahedron Lett. 1997, 38, 483-486. [14b] S. M. Dankwardt, D. B. Smith, J. A. Porco, Jr., C. H. Nguyen, Synlett 1997, 854-856. [14c] C. Kay, P. J. Murray, L. Sandow, A. B. Holmes, Tetrahedron Lett. 1997, 38, 6941-6944. [14d] H. S. M. Lu, M. Volk, Y. Kholodenko, E. Gooding, R. M. Hochstrasser, W. F. DeGrado, J. Am. Chem. Soc. 1997, 119, 7173-7180. [14e] J. F. Reichwein, R. M. J. Liskamp, Tetrahedron Lett. 1998, 39, 1243-1246. [14f] G. L. Bolton, Tetrahedron Lett. 1996, 37, 3433-3436. [14g] B. J. Backes, A. A. Virgilio, J. A. Ellman, J. Am. Chem. Soc. 1996, 118, 3055-3056. [14h] S C. Miller, T. S. Scanlan, J. Am. Chem. Soc. 1997, 119, 2301-2302. - For recent examples of peptide N-alkylation, [14i] B. Dörner, G. M. Husar, J. M. Ostresh, R. A. Houghten, Biorg. Med. Chem. 1996, 4, 709-715. [14j] K. Ohmori, T. Okuno, S. Nishiyama, S. Yamamura, Tetrahedron Lett. 1996, 37, 3467-3470.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6941-6944
    • Kay, C.1    Murray, P.J.2    Sandow, L.3    Holmes, A.B.4
  • 71
    • 0030801107 scopus 로고    scopus 로고
    • For recent examples of sulfonamide N-alkylation, see: [14a] K Wisniewski, A. S. Kolodziejczyk, Tetrahedron Lett. 1997, 38, 483-486. [14b] S. M. Dankwardt, D. B. Smith, J. A. Porco, Jr., C. H. Nguyen, Synlett 1997, 854-856. [14c] C. Kay, P. J. Murray, L. Sandow, A. B. Holmes, Tetrahedron Lett. 1997, 38, 6941-6944. [14d] H. S. M. Lu, M. Volk, Y. Kholodenko, E. Gooding, R. M. Hochstrasser, W. F. DeGrado, J. Am. Chem. Soc. 1997, 119, 7173-7180. [14e] J. F. Reichwein, R. M. J. Liskamp, Tetrahedron Lett. 1998, 39, 1243-1246. [14f] G. L. Bolton, Tetrahedron Lett. 1996, 37, 3433-3436. [14g] B. J. Backes, A. A. Virgilio, J. A. Ellman, J. Am. Chem. Soc. 1996, 118, 3055-3056. [14h] S C. Miller, T. S. Scanlan, J. Am. Chem. Soc. 1997, 119, 2301-2302. - For recent examples of peptide N-alkylation, [14i] B. Dörner, G. M. Husar, J. M. Ostresh, R. A. Houghten, Biorg. Med. Chem. 1996, 4, 709-715. [14j] K. Ohmori, T. Okuno, S. Nishiyama, S. Yamamura, Tetrahedron Lett. 1996, 37, 3467-3470.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 7173-7180
    • Lu, H.S.M.1    Volk, M.2    Kholodenko, Y.3    Gooding, E.4    Hochstrasser, R.M.5    DeGrado, W.F.6
  • 72
    • 0032485334 scopus 로고    scopus 로고
    • For recent examples of sulfonamide N-alkylation, see: [14a] K Wisniewski, A. S. Kolodziejczyk, Tetrahedron Lett. 1997, 38, 483-486. [14b] S. M. Dankwardt, D. B. Smith, J. A. Porco, Jr., C. H. Nguyen, Synlett 1997, 854-856. [14c] C. Kay, P. J. Murray, L. Sandow, A. B. Holmes, Tetrahedron Lett. 1997, 38, 6941-6944. [14d] H. S. M. Lu, M. Volk, Y. Kholodenko, E. Gooding, R. M. Hochstrasser, W. F. DeGrado, J. Am. Chem. Soc. 1997, 119, 7173-7180. [14e] J. F. Reichwein, R. M. J. Liskamp, Tetrahedron Lett. 1998, 39, 1243-1246. [14f] G. L. Bolton, Tetrahedron Lett. 1996, 37, 3433-3436. [14g] B. J. Backes, A. A. Virgilio, J. A. Ellman, J. Am. Chem. Soc. 1996, 118, 3055-3056. [14h] S C. Miller, T. S. Scanlan, J. Am. Chem. Soc. 1997, 119, 2301-2302. - For recent examples of peptide N-alkylation, [14i] B. Dörner, G. M. Husar, J. M. Ostresh, R. A. Houghten, Biorg. Med. Chem. 1996, 4, 709-715. [14j] K. Ohmori, T. Okuno, S. Nishiyama, S. Yamamura, Tetrahedron Lett. 1996, 37, 3467-3470.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1243-1246
    • Reichwein, J.F.1    Liskamp, R.M.J.2
  • 73
    • 0029978630 scopus 로고    scopus 로고
    • For recent examples of sulfonamide N-alkylation, see: [14a] K Wisniewski, A. S. Kolodziejczyk, Tetrahedron Lett. 1997, 38, 483-486. [14b] S. M. Dankwardt, D. B. Smith, J. A. Porco, Jr., C. H. Nguyen, Synlett 1997, 854-856. [14c] C. Kay, P. J. Murray, L. Sandow, A. B. Holmes, Tetrahedron Lett. 1997, 38, 6941-6944. [14d] H. S. M. Lu, M. Volk, Y. Kholodenko, E. Gooding, R. M. Hochstrasser, W. F. DeGrado, J. Am. Chem. Soc. 1997, 119, 7173-7180. [14e] J. F. Reichwein, R. M. J. Liskamp, Tetrahedron Lett. 1998, 39, 1243-1246. [14f] G. L. Bolton, Tetrahedron Lett. 1996, 37, 3433-3436. [14g] B. J. Backes, A. A. Virgilio, J. A. Ellman, J. Am. Chem. Soc. 1996, 118, 3055-3056. [14h] S C. Miller, T. S. Scanlan, J. Am. Chem. Soc. 1997, 119, 2301-2302. - For recent examples of peptide N-alkylation, [14i] B. Dörner, G. M. Husar, J. M. Ostresh, R. A. Houghten, Biorg. Med. Chem. 1996, 4, 709-715. [14j] K. Ohmori, T. Okuno, S. Nishiyama, S. Yamamura, Tetrahedron Lett. 1996, 37, 3467-3470.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3433-3436
    • Bolton, G.L.1
  • 74
    • 0001176887 scopus 로고    scopus 로고
    • For recent examples of sulfonamide N-alkylation, see: [14a] K Wisniewski, A. S. Kolodziejczyk, Tetrahedron Lett. 1997, 38, 483-486. [14b] S. M. Dankwardt, D. B. Smith, J. A. Porco, Jr., C. H. Nguyen, Synlett 1997, 854-856. [14c] C. Kay, P. J. Murray, L. Sandow, A. B. Holmes, Tetrahedron Lett. 1997, 38, 6941-6944. [14d] H. S. M. Lu, M. Volk, Y. Kholodenko, E. Gooding, R. M. Hochstrasser, W. F. DeGrado, J. Am. Chem. Soc. 1997, 119, 7173-7180. [14e] J. F. Reichwein, R. M. J. Liskamp, Tetrahedron Lett. 1998, 39, 1243-1246. [14f] G. L. Bolton, Tetrahedron Lett. 1996, 37, 3433-3436. [14g] B. J. Backes, A. A. Virgilio, J. A. Ellman, J. Am. Chem. Soc. 1996, 118, 3055-3056. [14h] S C. Miller, T. S. Scanlan, J. Am. Chem. Soc. 1997, 119, 2301-2302. - For recent examples of peptide N-alkylation, [14i] B. Dörner, G. M. Husar, J. M. Ostresh, R. A. Houghten, Biorg. Med. Chem. 1996, 4, 709-715. [14j] K. Ohmori, T. Okuno, S. Nishiyama, S. Yamamura, Tetrahedron Lett. 1996, 37, 3467-3470.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3055-3056
    • Backes, B.J.1    Virgilio, A.A.2    Ellman, J.A.3
  • 75
    • 0030936620 scopus 로고    scopus 로고
    • For recent examples of sulfonamide N-alkylation, see: [14a] K Wisniewski, A. S. Kolodziejczyk, Tetrahedron Lett. 1997, 38, 483-486. [14b] S. M. Dankwardt, D. B. Smith, J. A. Porco, Jr., C. H. Nguyen, Synlett 1997, 854-856. [14c] C. Kay, P. J. Murray, L. Sandow, A. B. Holmes, Tetrahedron Lett. 1997, 38, 6941-6944. [14d] H. S. M. Lu, M. Volk, Y. Kholodenko, E. Gooding, R. M. Hochstrasser, W. F. DeGrado, J. Am. Chem. Soc. 1997, 119, 7173-7180. [14e] J. F. Reichwein, R. M. J. Liskamp, Tetrahedron Lett. 1998, 39, 1243-1246. [14f] G. L. Bolton, Tetrahedron Lett. 1996, 37, 3433-3436. [14g] B. J. Backes, A. A. Virgilio, J. A. Ellman, J. Am. Chem. Soc. 1996, 118, 3055-3056. [14h] S C. Miller, T. S. Scanlan, J. Am. Chem. Soc. 1997, 119, 2301-2302. - For recent examples of peptide N-alkylation, [14i] B. Dörner, G. M. Husar, J. M. Ostresh, R. A. Houghten, Biorg. Med. Chem. 1996, 4, 709-715. [14j] K. Ohmori, T. Okuno, S. Nishiyama, S. Yamamura, Tetrahedron Lett. 1996, 37, 3467-3470.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 2301-2302
    • Miller, S.C.1    Scanlan, T.S.2
  • 76
    • 0343010435 scopus 로고    scopus 로고
    • For recent examples of sulfonamide N-alkylation, see: [14a] K Wisniewski, A. S. Kolodziejczyk, Tetrahedron Lett. 1997, 38, 483-486. [14b] S. M. Dankwardt, D. B. Smith, J. A. Porco, Jr., C. H. Nguyen, Synlett 1997, 854-856. [14c] C. Kay, P. J. Murray, L. Sandow, A. B. Holmes, Tetrahedron Lett. 1997, 38, 6941-6944. [14d] H. S. M. Lu, M. Volk, Y. Kholodenko, E. Gooding, R. M. Hochstrasser, W. F. DeGrado, J. Am. Chem. Soc. 1997, 119, 7173-7180. [14e] J. F. Reichwein, R. M. J. Liskamp, Tetrahedron Lett. 1998, 39, 1243-1246. [14f] G. L. Bolton, Tetrahedron Lett. 1996, 37, 3433-3436. [14g] B. J. Backes, A. A. Virgilio, J. A. Ellman, J. Am. Chem. Soc. 1996, 118, 3055-3056. [14h] S C. Miller, T. S. Scanlan, J. Am. Chem. Soc. 1997, 119, 2301-2302. - For recent examples of peptide N-alkylation, [14i] B. Dörner, G. M. Husar, J. M. Ostresh, R. A. Houghten, Biorg. Med. Chem. 1996, 4, 709-715. [14j] K. Ohmori, T. Okuno, S. Nishiyama, S. Yamamura, Tetrahedron Lett. 1996, 37, 3467-3470.
    • (1996) Biorg. Med. Chem. , vol.4 , pp. 709-715
    • Dörner, B.1    Husar, G.M.2    Ostresh, J.M.3    Houghten, R.A.4
  • 77
    • 0030009931 scopus 로고    scopus 로고
    • For recent examples of sulfonamide N-alkylation, see: [14a] K Wisniewski, A. S. Kolodziejczyk, Tetrahedron Lett. 1997, 38, 483-486. [14b] S. M. Dankwardt, D. B. Smith, J. A. Porco, Jr., C. H. Nguyen, Synlett 1997, 854-856. [14c] C. Kay, P. J. Murray, L. Sandow, A. B. Holmes, Tetrahedron Lett. 1997, 38, 6941-6944. [14d] H. S. M. Lu, M. Volk, Y. Kholodenko, E. Gooding, R. M. Hochstrasser, W. F. DeGrado, J. Am. Chem. Soc. 1997, 119, 7173-7180. [14e] J. F. Reichwein, R. M. J. Liskamp, Tetrahedron Lett. 1998, 39, 1243-1246. [14f] G. L. Bolton, Tetrahedron Lett. 1996, 37, 3433-3436. [14g] B. J. Backes, A. A. Virgilio, J. A. Ellman, J. Am. Chem. Soc. 1996, 118, 3055-3056. [14h] S C. Miller, T. S. Scanlan, J. Am. Chem. Soc. 1997, 119, 2301-2302. - For recent examples of peptide N-alkylation, [14i] B. Dörner, G. M. Husar, J. M. Ostresh, R. A. Houghten, Biorg. Med. Chem. 1996, 4, 709-715. [14j] K. Ohmori, T. Okuno, S. Nishiyama, S. Yamamura, Tetrahedron Lett. 1996, 37, 3467-3470.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3467-3470
    • Ohmori, K.1    Okuno, T.2    Nishiyama, S.3    Yamamura, S.4
  • 79
    • 84958232329 scopus 로고    scopus 로고
    • PEG Grafted Polystyrene Tentacle Polymers . Physico-Chemical Properties and Application in Chemical Synthesis
    • chapter 16, Ed.: G. Jung, VCH, Weinheim
    • [16a] W. Rapp, PEG Grafted Polystyrene Tentacle Polymers . Physico-Chemical Properties and Application in Chemical Synthesis, chapter 16 in Combinatorial Peptide and Nonpeptide Libraries (Ed.: G. Jung), VCH, Weinheim. 1996, p. 425-464.
    • (1996) Combinatorial Peptide and Nonpeptide Libraries , pp. 425-464
    • Rapp, W.1
  • 81
    • 2842516447 scopus 로고    scopus 로고
    • TentaGel is a registred trademark of Fa. Rapp Polymere GmbH, Tübingen, Germany
    • [16c] TentaGel is a registred trademark of Fa. Rapp Polymere GmbH, Tübingen, Germany.
  • 82
    • 0001125895 scopus 로고    scopus 로고
    • and references therein
    • [17a] C. P. Holmes, J. Org. Chem. 1997, 62, 2370-2380, and references therein.
    • (1997) J. Org. Chem. , vol.62 , pp. 2370-2380
    • Holmes, C.P.1
  • 83
    • 2842581027 scopus 로고    scopus 로고
    • Finoc-aminoethyl-Photolinker Nova-Syn TG resin is commercialized by Calbiochem-Novabiochem AG under an exclusive license from Affimax Research Institute
    • [17b] Finoc-aminoethyl-Photolinker Nova-Syn TG resin is commercialized by Calbiochem-Novabiochem AG under an exclusive license from Affimax Research Institute.
  • 90
    • 2842557718 scopus 로고    scopus 로고
    • note
    • The BPB test solution was prepared by diluting with DCM (4.5 ml) 0.5 ml of a 0.5% BPB solution in DMA. Some resin beads were put into a test tube and four drops of the BPB solution were added. The excess of indicator was removed with a micro syringe and the beads were washed with DCM. The colour of the resin beads was checked by microscope: blue indicates the presence of a high concentration of free amino groups; green indicates the presence of a low concentration of free amino groups; yellow indicates that free amino groups are not present. For other details, see ref.[18].
  • 91
    • 0028577207 scopus 로고
    • According to this approach, pools of compounds are prepared so that each separate pool has defined building blocks at either one or two positions, and all combinations of building blocks are incorporated at the remaining positions. The optimal building blocks at the defined position is selected by determining which pool has the highest biological activity. A second round of synthesis is then performed with the selected building block in place at the initially defined position, in order to prepare pools where the next defined position is introduced. This deconvolution process is then repeated until all the positions are defined See: C T. Dooley, N. N. Chung, B. C. Wilkes, P. W. Schiller, J. M. Bidlack, G. W. Pasternak, R. A. Houghten, Science 1994, 266, 2019-2022.
    • (1994) Science , vol.266 , pp. 2019-2022
    • Dooley, C.T.1    Chung, N.N.2    Wilkes, B.C.3    Schiller, P.W.4    Bidlack, J.M.5    Pasternak, G.W.6    Houghten, R.A.7
  • 97
    • 0011741220 scopus 로고
    • 2) γ-amino-α,β-unsaturated esters, see: M. T. Reetz, D. Roehrig, Angew. Chem 1989, 101, 1732-1734, Angew. Chem. Int. Ed. Engl. 1989, 28, 1706-1709; M. T. Reetz, D. Roehrig, K. Harms, G. Frenking, Tetrahedron Lett. 1994, 35, 8765-8768; S. Hanessian, W. Wang, Y. Gai, Tetrahedron Lett. 1996, 37, 7477-7480; J. S. Plummer, L. A Emery, M. A. Stier, M. J Suto Tetrahedron Lett. 1993, 34, 7529-7532.
    • (1989) Angew. Chem , vol.101 , pp. 1732-1734
    • Reetz, M.T.1    Roehrig, D.2
  • 98
    • 0024841697 scopus 로고
    • 2) γ-amino-α,β-unsaturated esters, see: M. T. Reetz, D. Roehrig, Angew. Chem 1989, 101, 1732-1734, Angew. Chem. Int. Ed. Engl. 1989, 28, 1706-1709; M. T. Reetz, D. Roehrig, K. Harms, G. Frenking, Tetrahedron Lett. 1994, 35, 8765-8768; S. Hanessian, W. Wang, Y. Gai, Tetrahedron Lett. 1996, 37, 7477-7480; J. S. Plummer, L. A Emery, M. A. Stier, M. J Suto Tetrahedron Lett. 1993, 34, 7529-7532.
    • (1989) Angew. Chem. Int. Ed. Engl. , vol.28 , pp. 1706-1709
  • 99
    • 0028116566 scopus 로고
    • 2) γ-amino-α,β-unsaturated esters, see: M. T. Reetz, D. Roehrig, Angew. Chem 1989, 101, 1732-1734, Angew. Chem. Int. Ed. Engl. 1989, 28, 1706-1709; M. T. Reetz, D. Roehrig, K. Harms, G. Frenking, Tetrahedron Lett. 1994, 35, 8765-8768; S. Hanessian, W. Wang, Y. Gai, Tetrahedron Lett. 1996, 37, 7477-7480; J. S. Plummer, L. A Emery, M. A. Stier, M. J Suto Tetrahedron Lett. 1993, 34, 7529-7532.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8765-8768
    • Reetz, M.T.1    Roehrig, D.2    Harms, K.3    Frenking, G.4
  • 100
    • 0030583508 scopus 로고    scopus 로고
    • 2) γ-amino-α,β-unsaturated esters, see: M. T. Reetz, D. Roehrig, Angew. Chem 1989, 101, 1732-1734, Angew. Chem. Int. Ed. Engl. 1989, 28, 1706-1709; M. T. Reetz, D. Roehrig, K. Harms, G. Frenking, Tetrahedron Lett. 1994, 35, 8765-8768; S. Hanessian, W. Wang, Y. Gai, Tetrahedron Lett. 1996, 37, 7477-7480; J. S. Plummer, L. A Emery, M. A. Stier, M. J Suto Tetrahedron Lett. 1993, 34, 7529-7532.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7477-7480
    • Hanessian, S.1    Wang, W.2    Gai, Y.3
  • 101
    • 0027366768 scopus 로고
    • 2) γ-amino-α,β-unsaturated esters, see: M. T. Reetz, D. Roehrig, Angew. Chem 1989, 101, 1732-1734, Angew. Chem. Int. Ed. Engl. 1989, 28, 1706-1709; M. T. Reetz, D. Roehrig, K. Harms, G. Frenking, Tetrahedron Lett. 1994, 35, 8765-8768; S. Hanessian, W. Wang, Y. Gai, Tetrahedron Lett. 1996, 37, 7477-7480; J. S. Plummer, L. A Emery, M. A. Stier, M. J Suto Tetrahedron Lett. 1993, 34, 7529-7532.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7529-7532
    • Plummer, J.S.1    Emery, L.A.2    Stier, M.A.3    Suto, M.J.4


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