메뉴 건너뛰기




Volumn 121, Issue 50, 1999, Pages 11638-11643

A biomimetic approach to asymmetric acyl transfer catalysis

Author keywords

[No Author keywords available]

Indexed keywords

HISTIDINE; OCTAPEPTIDE; TETRAPEPTIDE;

EID: 0033596302     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9931776     Document Type: Article
Times cited : (233)

References (65)
  • 2
    • 0000085691 scopus 로고    scopus 로고
    • and references therein
    • For reviews, see: (a) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Elsevier: Oxford, U.K., 1994. (b) Johnson, C. R. Acc. Chem. Res. 1998, 31, 333-341 and references therein.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 333-341
    • Johnson, C.R.1
  • 8
    • 0029158641 scopus 로고
    • For impressive examples, see: (a) Lee, T.; Sakowicz, R.; Martichonok, V.; Hogan, J. K.; Gold, M.; Jones, J. B. Acta Chem. Scand. 1996, 50, 697-706. (b) Derewenda, Z. S.; Wei, Y. J. Am. Chem. Soc. 1995, 117, 2104-2105.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 2104-2105
    • Derewenda, Z.S.1    Wei, Y.2
  • 13
    • 0000507166 scopus 로고
    • For representative examples, see: (a) Jeong, K.-S.; Muhldorf, A. V.; Rebek, J., Jr. J. Am. Chem. Soc. 1990, 112, 6144-6145. (b) Liu, R.; Sanderson, P. E. J.; Still, W. C. J. Org. Chem. 1990, 55, 5184-5186. (c) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089- 5098. (d) Garcia-Tellado, F.; Albert, J.; Fan, E.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1991, 1761-1763. (e) Wilcox, C. S. Chem. Soc. Rev. 1993, 22, 383-395.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6144-6145
    • Jeong, K.-S.1    Muhldorf, A.V.2    Rebek J., Jr.3
  • 14
    • 0025118379 scopus 로고
    • For representative examples, see: (a) Jeong, K.-S.; Muhldorf, A. V.; Rebek, J., Jr. J. Am. Chem. Soc. 1990, 112, 6144-6145. (b) Liu, R.; Sanderson, P. E. J.; Still, W. C. J. Org. Chem. 1990, 55, 5184-5186. (c) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089- 5098. (d) Garcia-Tellado, F.; Albert, J.; Fan, E.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1991, 1761-1763. (e) Wilcox, C. S. Chem. Soc. Rev. 1993, 22, 383-395.
    • (1990) J. Org. Chem. , vol.55 , pp. 5184-5186
    • Liu, R.1    Sanderson, P.E.J.2    Still, W.C.3
  • 15
    • 0000905639 scopus 로고
    • For representative examples, see: (a) Jeong, K.-S.; Muhldorf, A. V.; Rebek, J., Jr. J. Am. Chem. Soc. 1990, 112, 6144-6145. (b) Liu, R.; Sanderson, P. E. J.; Still, W. C. J. Org. Chem. 1990, 55, 5184-5186. (c) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089-5098. (d) Garcia-Tellado, F.; Albert, J.; Fan, E.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1991, 1761-1763. (e) Wilcox, C. S. Chem. Soc. Rev. 1993, 22, 383-395.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 5089-5098
    • Cristofaro, M.F.1    Chamberlin, A.R.2
  • 16
    • 37049068253 scopus 로고
    • For representative examples, see: (a) Jeong, K.-S.; Muhldorf, A. V.; Rebek, J., Jr. J. Am. Chem. Soc. 1990, 112, 6144-6145. (b) Liu, R.; Sanderson, P. E. J.; Still, W. C. J. Org. Chem. 1990, 55, 5184-5186. (c) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089- 5098. (d) Garcia-Tellado, F.; Albert, J.; Fan, E.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1991, 1761-1763. (e) Wilcox, C. S. Chem. Soc. Rev. 1993, 22, 383-395.
    • (1991) J. Chem. Soc., Chem. Commun. , pp. 1761-1763
    • Garcia-Tellado, F.1    Albert, J.2    Fan, E.3    Hamilton, A.D.4
  • 17
    • 12044259565 scopus 로고
    • For representative examples, see: (a) Jeong, K.-S.; Muhldorf, A. V.; Rebek, J., Jr. J. Am. Chem. Soc. 1990, 112, 6144-6145. (b) Liu, R.; Sanderson, P. E. J.; Still, W. C. J. Org. Chem. 1990, 55, 5184-5186. (c) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089- 5098. (d) Garcia-Tellado, F.; Albert, J.; Fan, E.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1991, 1761-1763. (e) Wilcox, C. S. Chem. Soc. Rev. 1993, 22, 383-395.
    • (1993) Chem. Soc. Rev. , vol.22 , pp. 383-395
    • Wilcox, C.S.1
  • 18
    • 0003554758 scopus 로고    scopus 로고
    • For representative enantioselective catalysts that rely exclusively on peptide or a peptide-like functionality, see: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901-4902. (b) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910- 4911. (c) Cleij, M. C.; Drenth, W.; Nolte, R. J. M. J. Org. Chem. 1991, 56, 3883-3891. (d) Tanaka, K.; Mori, A.; Inoue, S. J. Org. Chem. 1990, 55, 181-185. (e) Agami, C.; Puchot, C.; Sevestre, H. Tetrahedron Lett. 1986, 27, 1501-1504. (f) For a representative approach that involves a de novo designed protein, see: Broo, K. S.; Brive, L.; Ahlberg, P.; Baltzer, L. J. Am. Chem. Soc. 1997, 119, 11362-11372.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 4901-4902
    • Sigman, M.S.1    Jacobsen, E.N.2
  • 19
    • 0029990764 scopus 로고    scopus 로고
    • For representative enantioselective catalysts that rely exclusively on peptide or a peptide-like functionality, see: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901-4902. (b) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910-4911. (c) Cleij, M. C.; Drenth, W.; Nolte, R. J. M. J. Org. Chem. 1991, 56, 3883-3891. (d) Tanaka, K.; Mori, A.; Inoue, S. J. Org. Chem. 1990, 55, 181-185. (e) Agami, C.; Puchot, C.; Sevestre, H. Tetrahedron Lett. 1986, 27, 1501-1504. (f) For a representative approach that involves a de novo designed protein, see: Broo, K. S.; Brive, L.; Ahlberg, P.; Baltzer, L. J. Am. Chem. Soc. 1997, 119, 11362-11372.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 4910-4911
    • Iyer, M.S.1    Gigstad, K.M.2    Namdev, N.D.3    Lipton, M.4
  • 20
    • 0000402140 scopus 로고
    • For representative enantioselective catalysts that rely exclusively on peptide or a peptide-like functionality, see: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901-4902. (b) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910- 4911. (c) Cleij, M. C.; Drenth, W.; Nolte, R. J. M. J. Org. Chem. 1991, 56, 3883-3891. (d) Tanaka, K.; Mori, A.; Inoue, S. J. Org. Chem. 1990, 55, 181-185. (e) Agami, C.; Puchot, C.; Sevestre, H. Tetrahedron Lett. 1986, 27, 1501-1504. (f) For a representative approach that involves a de novo designed protein, see: Broo, K. S.; Brive, L.; Ahlberg, P.; Baltzer, L. J. Am. Chem. Soc. 1997, 119, 11362-11372.
    • (1991) J. Org. Chem. , vol.56 , pp. 3883-3891
    • Cleij, M.C.1    Drenth, W.2    Nolte, R.J.M.3
  • 21
    • 0000624398 scopus 로고
    • For representative enantioselective catalysts that rely exclusively on peptide or a peptide-like functionality, see: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901-4902. (b) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910- 4911. (c) Cleij, M. C.; Drenth, W.; Nolte, R. J. M. J. Org. Chem. 1991, 56, 3883-3891. (d) Tanaka, K.; Mori, A.; Inoue, S. J. Org. Chem. 1990, 55, 181-185. (e) Agami, C.; Puchot, C.; Sevestre, H. Tetrahedron Lett. 1986, 27, 1501-1504. (f) For a representative approach that involves a de novo designed protein, see: Broo, K. S.; Brive, L.; Ahlberg, P.; Baltzer, L. J. Am. Chem. Soc. 1997, 119, 11362-11372.
    • (1990) J. Org. Chem. , vol.55 , pp. 181-185
    • Tanaka, K.1    Mori, A.2    Inoue, S.3
  • 22
    • 0001332919 scopus 로고
    • For representative enantioselective catalysts that rely exclusively on peptide or a peptide-like functionality, see: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901-4902. (b) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910- 4911. (c) Cleij, M. C.; Drenth, W.; Nolte, R. J. M. J. Org. Chem. 1991, 56, 3883-3891. (d) Tanaka, K.; Mori, A.; Inoue, S. J. Org. Chem. 1990, 55, 181-185. (e) Agami, C.; Puchot, C.; Sevestre, H. Tetrahedron Lett. 1986, 27, 1501-1504. (f) For a representative approach that involves a de novo designed protein, see: Broo, K. S.; Brive, L.; Ahlberg, P.; Baltzer, L. J. Am. Chem. Soc. 1997, 119, 11362-11372.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 1501-1504
    • Agami, C.1    Puchot, C.2    Sevestre, H.3
  • 23
    • 0031587461 scopus 로고    scopus 로고
    • For representative enantioselective catalysts that rely exclusively on peptide or a peptide-like functionality, see: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901-4902. (b) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910- 4911. (c) Cleij, M. C.; Drenth, W.; Nolte, R. J. M. J. Org. Chem. 1991, 56, 3883-3891. (d) Tanaka, K.; Mori, A.; Inoue, S. J. Org. Chem. 1990, 55, 181-185. (e) Agami, C.; Puchot, C.; Sevestre, H. Tetrahedron Lett. 1986, 27, 1501-1504. (f) For a representative approach that involves a de novo designed protein, see: Broo, K. S.; Brive, L.; Ahlberg, P.; Baltzer, L. J. Am. Chem. Soc. 1997, 119, 11362-11372.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 11362-11372
    • Broo, K.S.1    Brive, L.2    Ahlberg, P.3    Baltzer, L.4
  • 28
    • 0020001240 scopus 로고
    • (c) For the N-alkylimidazoles, a general base-type mechanism cannot be excluded. See: Pandit, N. K.; Connors, K. A. J. Pharm. Sci. 1982, 71, 485-491.
    • (1982) J. Pharm. Sci. , vol.71 , pp. 485-491
    • Pandit, N.K.1    Connors, K.A.2
  • 29
    • 0029876822 scopus 로고    scopus 로고
    • For representative, nonenzymatic enantioselective nucleophilic catalysts, see: (a) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. (b) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813- 5814. (c) Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091-5092. (d) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170. (e) Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397-400.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1809-1810
    • Vedejs, E.1    Chen, X.2
  • 30
    • 0033597606 scopus 로고    scopus 로고
    • For representative, nonenzymatic enantioselective nucleophilic catalysts, see: (a) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809- 1810. (b) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813-5814. (c) Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091-5092. (d) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170. (e) Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397-400.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 5813-5814
    • Vedejs, E.1    Daugulis, O.2
  • 31
    • 0033516290 scopus 로고    scopus 로고
    • For representative, nonenzymatic enantioselective nucleophilic catalysts, see: (a) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809- 1810. (b) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813- 5814. (c) Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091-5092. (d) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170. (e) Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397-400.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 5091-5092
    • Tao, B.1    Ruble, J.C.2    Hoic, D.A.3    Fu, G.C.4
  • 32
    • 0030961223 scopus 로고    scopus 로고
    • For representative, nonenzymatic enantioselective nucleophilic catalysts, see: (a) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809- 1810. (b) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813- 5814. (c) Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091-5092. (d) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170. (e) Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397-400.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 3169-3170
    • Kawabata, T.1    Nagato, M.2    Takasu, K.3    Fuji, K.4
  • 33
    • 0032576797 scopus 로고    scopus 로고
    • For representative, nonenzymatic enantioselective nucleophilic catalysts, see: (a) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809- 1810. (b) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813- 5814. (c) Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091-5092. (d) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170. (e) Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397-400.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 397-400
    • Oriyama, T.1    Imai, K.2    Hosoya, T.3    Sano, T.4
  • 42
    • 0342871817 scopus 로고    scopus 로고
    • Crystallographic data may be found in the Supporting Information
    • Crystallographic data may be found in the Supporting Information.
  • 43
    • 0002585041 scopus 로고
    • Peptide 4 does not catalyze acyl transfer under the present conditions at an appreciable rate. This experiment rules out amide catalysis as the sole source of the reactivity and selectivity we observe: Titskii, G. D.; Litvinenko, L. M. Zh. Obshch. Khim. 1970, 40, 2680-2688.
    • (1970) Zh. Obshch. Khim. , vol.40 , pp. 2680-2688
    • Titskii, G.D.1    Litvinenko, L.M.2
  • 44
    • 85050296727 scopus 로고
    • slow) were calculated according to the method of Kagan. See: Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330.
    • (1988) Top. Stereochem. , vol.18 , pp. 249-330
    • Kagan, H.B.1    Fiaud, J.C.2
  • 45
    • 0343742361 scopus 로고    scopus 로고
    • 8 See the Supporting Information for details
    • 8 See the Supporting Information for details.
  • 46
    • 0001501830 scopus 로고    scopus 로고
    • (c) The absolute sense of chirality of 5-Ac and 5 was assigned according to the method of Jacobsen: Schaus, S. E.; Larrow, J. F.; Jacobsen, E. N. J. Org. Chem. 1997, 62, 4197-4199.
    • (1997) J. Org. Chem. , vol.62 , pp. 4197-4199
    • Schaus, S.E.1    Larrow, J.F.2    Jacobsen, E.N.3
  • 47
    • 0029931671 scopus 로고    scopus 로고
    • For comparative examples of the conformational influence of L-Pro vs D-Pro residues in short peptides, see: (a) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975-6985. (b) Karle, I. L.; Awasthi, S. K.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8189- 8193. (c) Ragohothama, S. R.; Awasthi, S. K.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1998, 137-143.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 6975-6985
    • Haque, T.S.1    Little, J.C.2    Gellman, S.H.3
  • 48
    • 0029758829 scopus 로고    scopus 로고
    • For comparative examples of the conformational influence of L-Pro vs D-Pro residues in short peptides, see: (a) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975-6985. (b) Karle, I. L.; Awasthi, S. K.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8189-8193. (c) Ragohothama, S. R.; Awasthi, S. K.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1998, 137-143.
    • (1996) Proc. Natl. Acad. Sci. U.S.A. , vol.93 , pp. 8189-8193
    • Karle, I.L.1    Awasthi, S.K.2    Balaram, P.3
  • 49
    • 0346837918 scopus 로고    scopus 로고
    • For comparative examples of the conformational influence of L-Pro vs D-Pro residues in short peptides, see: (a) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975-6985. (b) Karle, I. L.; Awasthi, S. K.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8189- 8193. (c) Ragohothama, S. R.; Awasthi, S. K.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1998, 137-143.
    • (1998) J. Chem. Soc., Perkin Trans. 2 , pp. 137-143
    • Ragohothama, S.R.1    Awasthi, S.K.2    Balaram, P.3
  • 50
    • 0342437259 scopus 로고    scopus 로고
    • note
    • Peptides were prepared according to standard solid-phase peptide synthesis protocols and purified by silica gel chromatography, or preparative HPLC. See the Supporting Information for details.
  • 57
    • 0033612175 scopus 로고    scopus 로고
    • We thank Heather D. Maynard for providing a sample of the phosphine
    • Following the catalytic RCM reaction, the resin was treated with tris(hydroxymethyl)phosphine to facilitate removal of the Ru-containing entities: Maynard, H. D.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 4137-4140. We thank Heather D. Maynard for providing a sample of the phosphine.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 4137-4140
    • Maynard, H.D.1    Grubbs, R.H.2
  • 61
    • 0343742359 scopus 로고    scopus 로고
    • note
    • Kinetic experiments were also carried out on the single enantiomers. Pseudo-first-order kinetics were observed in these experiments as well.
  • 62
    • 0342871813 scopus 로고    scopus 로고
    • note
    • Under more concentrated conditions (200 mM in substrate), DMAP is more active than tetrapeptide 7. Since absolute selectivities are also lower with peptide catalysis at higher concentrations, we tentatively attribute this phenomenon to peptide-catalyst deactivation through aggregation. See the Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.