메뉴 건너뛰기




Volumn , Issue 6, 1998, Pages 945-959

Synthesis of chiral vinylogous sulfonamidopeptides (vs-peptides)

Author keywords

Iterative synthesis; N Boc amino aldehydes; Pseudopeptides; Sulfonamides; Vinylogous sulfonamidopeptides

Indexed keywords


EID: 0003160052     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199806)1998:6<945::aid-ejoc945>3.0.co;2-3     Document Type: Article
Times cited : (20)

References (91)
  • 1
    • 0042953146 scopus 로고
    • [1a] For recent reviews, see: R. M. J. Liskamp, Angew. Chem. 1994, 106, 661-664, Angew. Chem. Int. Ed. Engl. 1994, 33, 633-636; S. Borman, C&EN 1997, June 16, 32-35.
    • (1994) Angew. Chem. , vol.106 , pp. 661-664
    • Liskamp, R.M.J.1
  • 2
    • 33748226252 scopus 로고
    • [1a] For recent reviews, see: R. M. J. Liskamp, Angew. Chem. 1994, 106, 661-664, Angew. Chem. Int. Ed. Engl. 1994, 33, 633-636; S. Borman, C&EN 1997, June 16, 32-35.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 633-636
  • 3
    • 0006988850 scopus 로고    scopus 로고
    • June 16
    • [1a] For recent reviews, see: R. M. J. Liskamp, Angew. Chem. 1994, 106, 661-664, Angew. Chem. Int. Ed. Engl. 1994, 33, 633-636; S. Borman, C&EN 1997, June 16, 32-35.
    • (1997) C&EN , pp. 32-35
    • Borman, S.1
  • 9
    • 0000517240 scopus 로고
    • [1f] 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
  • 18
    • 0000734566 scopus 로고
    • [2a] 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
  • 19
    • 33745502124 scopus 로고
    • [2a] 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
  • 20
    • 0001215147 scopus 로고
    • [2b] J. Gante, Angew Chem. 1994, 106, 1780-1802, Angew. Chem. Int. Ed. Engl 1994, 33, 1699-1720.
    • (1994) Angew Chem. , vol.106 , pp. 1780-1802
    • Gante, J.1
  • 21
    • 0028038601 scopus 로고
    • [2b] J. Gante, Angew Chem. 1994, 106, 1780-1802, Angew. Chem. Int. Ed. Engl 1994, 33, 1699-1720.
    • (1994) Angew. Chem. Int. Ed. Engl , vol.33 , pp. 1699-1720
  • 43
    • 2742525517 scopus 로고    scopus 로고
    • note
    • 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.
  • 46
    • 33748242808 scopus 로고
    • [8b] 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
  • 48
    • 33748831629 scopus 로고
    • [8c] 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
  • 49
  • 50
    • 0000455904 scopus 로고
    • [9a] For a preliminary communication, 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
  • 51
    • 2742527732 scopus 로고    scopus 로고
    • Italian Patent - Application 17 May 1994, N. MI94 A 000989; PCT Int. Appl. EP 95-01788, 11 May 1995
    • [9b] 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.
    • Gennari, C.1    Salom, B.2    Potenza, D.3
  • 53
    • 33745424910 scopus 로고
    • [11a] M. T. Reetz, Angew. Chem. 1991, 103, 1559, Angew. Chem. Int. Ed. Engl. 1991, 30, 1531-1546.
    • (1991) Angew. Chem. , vol.103 , pp. 1559
    • Reetz, M.T.1
  • 54
    • 33745424910 scopus 로고
    • [11a] M. T. Reetz, Angew. Chem. 1991, 103, 1559, Angew. Chem. Int. Ed. Engl. 1991, 30, 1531-1546.
    • (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 1531-1546
  • 56
    • 33748813785 scopus 로고
    • [11b] M. T. Reetz, J. Kanand, N. Griebenow, K. Harms, Angew. Chem. 1992, 104, 1638, Angew. Chem Int. Ed. Engl. 1992, 31, 1626-1629.
    • (1992) Angew. Chem Int. Ed. Engl. , vol.31 , pp. 1626-1629
  • 60
    • 0000341555 scopus 로고
    • It was noticed that the nitrogen protective group and the temperature of storage are important parameters to control and avoid loss of enantiomeric purity: for example, using tbutoxycarbonyl (Boc) and keeping the α-amino aldehydes at -30°C for 24 h, little racemization was detected (e.e. ≥ 96%), see : K. E. Rittle, C. F. Homnick, G. S. Ponticello, B. E. Evans, J. Org. Chem 1982, 47, 3016-3018.
    • (1982) J. Org. Chem , vol.47 , pp. 3016-3018
    • Rittle, K.E.1    Homnick, C.F.2    Ponticello, G.S.3    Evans, B.E.4
  • 69
    • 2742524367 scopus 로고    scopus 로고
    • note
    • In the only case of the α,β-unsaturated sulfonate derived from phenylalanine the (Z) diastereoisomer (10%) was identified and easily separated from the major (E) diastereoisomer (90%) by flash chromatography. In all other cases no trace of the (Z) diastereoisomer could be identified.
  • 86
    • 2742613534 scopus 로고    scopus 로고
    • note
    • Starting from non-crystallized 6, NMR analysis of the Mosher's amides revealed a a ≥98:2 ratio of diastereoisomers, while starting from recrystallized 6, the Mosher's amides were obtained as single compounds within the limits of NMR detection (>99:1), see the Experimental Section.
  • 87
    • 85087581721 scopus 로고    scopus 로고
    • note
    • 13C-NMR analysis of vs-dipeptides 30 revealed them to be single diastereomers, see the Experimental Section.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.