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Volumn 38, Issue 7, 1997, Pages 1265-1268

Synthesis of totally chiral, multiple armed, poly Glu and poly Asp scaffoldings on bifunctional adamantane core

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE;

EID: 0031575601     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00054-3     Document Type: Article
Times cited : (47)

References (21)
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    • 2. Tomalia, D.A.; Naylor, A.M.; Goddard III, W.A. Angew. Chem., Int. Ed. Engl. 1990, 29, 138; Frechet, J.M. J. Science 1994, 263, 1710. To the best of our knowledge although trifunctional amino acid monomers, for example, Lysine (Denkewalter, R.G.; Kole, J.F.; Lukasavage, W.J. U.S. Pat. 4410688, 1979; Rao, C.; Tam, J.P. J. Am. Chem. Soc. 1994, 116, 6975) and Glutamic acid (Twyman, L.J.; Beezer, A.E.; Mitchell, J.C. Tet. Lett. 1994, 35, 4423) have been used as building blocks for the construction of peptide dendrimers, there is no example in literature where these scaffoldings are supported on conformationally well-defined rigid molecular templates.
    • (1990) Angew. Chem., Int. Ed. Engl. , vol.29 , pp. 138
    • Tomalia, D.A.1    Naylor, A.M.2    Goddard W.A. III3
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    • 2. Tomalia, D.A.; Naylor, A.M.; Goddard III, W.A. Angew. Chem., Int. Ed. Engl. 1990, 29, 138; Frechet, J.M. J. Science 1994, 263, 1710. To the best of our knowledge although trifunctional amino acid monomers, for example, Lysine (Denkewalter, R.G.; Kole, J.F.; Lukasavage, W.J. U.S. Pat. 4410688, 1979; Rao, C.; Tam, J.P. J. Am. Chem. Soc. 1994, 116, 6975) and Glutamic acid (Twyman, L.J.; Beezer, A.E.; Mitchell, J.C. Tet. Lett. 1994, 35, 4423) have been used as building blocks for the construction of peptide dendrimers, there is no example in literature where these scaffoldings are supported on conformationally well-defined rigid molecular templates.
    • (1994) Science , vol.263 , pp. 1710
    • Frechet, J.M.J.1
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    • W.J. U.S. Pat. 4410688, 1979
    • 2. Tomalia, D.A.; Naylor, A.M.; Goddard III, W.A. Angew. Chem., Int. Ed. Engl. 1990, 29, 138; Frechet, J.M. J. Science 1994, 263, 1710. To the best of our knowledge although trifunctional amino acid monomers, for example, Lysine (Denkewalter, R.G.; Kole, J.F.; Lukasavage, W.J. U.S. Pat. 4410688, 1979; Rao, C.; Tam, J.P. J. Am. Chem. Soc. 1994, 116, 6975) and Glutamic acid (Twyman, L.J.; Beezer, A.E.; Mitchell, J.C. Tet. Lett. 1994, 35, 4423) have been used as building blocks for the construction of peptide dendrimers, there is no example in literature where these scaffoldings are supported on conformationally well-defined rigid molecular templates.
    • Denkewalter, R.G.1    Kole, J.F.2
  • 8
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    • 2. Tomalia, D.A.; Naylor, A.M.; Goddard III, W.A. Angew. Chem., Int. Ed. Engl. 1990, 29, 138; Frechet, J.M. J. Science 1994, 263, 1710. To the best of our knowledge although trifunctional amino acid monomers, for example, Lysine (Denkewalter, R.G.; Kole, J.F.; Lukasavage, W.J. U.S. Pat. 4410688, 1979; Rao, C.; Tam, J.P. J. Am. Chem. Soc. 1994, 116, 6975) and Glutamic acid (Twyman, L.J.; Beezer, A.E.; Mitchell, J.C. Tet. Lett. 1994, 35, 4423) have been used as building blocks for the construction of peptide dendrimers, there is no example in literature where these scaffoldings are supported on conformationally well-defined rigid molecular templates.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 6975
    • Rao, C.1    Tam, J.P.2
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    • 2. Tomalia, D.A.; Naylor, A.M.; Goddard III, W.A. Angew. Chem., Int. Ed. Engl. 1990, 29, 138; Frechet, J.M. J. Science 1994, 263, 1710. To the best of our knowledge although trifunctional amino acid monomers, for example, Lysine (Denkewalter, R.G.; Kole, J.F.; Lukasavage, W.J. U.S. Pat. 4410688, 1979; Rao, C.; Tam, J.P. J. Am. Chem. Soc. 1994, 116, 6975) and Glutamic acid (Twyman, L.J.; Beezer, A.E.; Mitchell, J.C. Tet. Lett. 1994, 35, 4423) have been used as building blocks for the construction of peptide dendrimers, there is no example in literature where these scaffoldings are supported on conformationally well-defined rigid molecular templates.
    • (1994) Tet. Lett. , vol.35 , pp. 4423
    • Twyman, L.J.1    Beezer, A.E.2    Mitchell, J.C.3
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    • 5. Tam, J.P. Proc. Natl. Acad. Sci. U.S.A. 1988, 55, 5409; Defoort, J.P.; Nardelli, B;. Huang, W.; Ho, D.; Tam, J.P. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 3879; Nardelli, B.; Lu, Y.A.; Shiu, D.R.; Dalpieire-Defoort, C.; Profy, A.T.; Tam, J.P. J. Immun. 1992, 148, 914; Tam, J.P.; Clavijo, P.; Lu, Y.A.; Nussenzweig, V.; Nussenzweig, R.; Zavala, F. J. Exp. Med. 1990, 171, 299.
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    • 5. Tam, J.P. Proc. Natl. Acad. Sci. U.S.A. 1988, 55, 5409; Defoort, J.P.; Nardelli, B;. Huang, W.; Ho, D.; Tam, J.P. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 3879; Nardelli, B.; Lu, Y.A.; Shiu, D.R.; Dalpieire-Defoort, C.; Profy, A.T.; Tam, J.P. J. Immun. 1992, 148, 914; Tam, J.P.; Clavijo, P.; Lu, Y.A.; Nussenzweig, V.; Nussenzweig, R.; Zavala, F. J. Exp. Med. 1990, 171, 299.
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    • 5. Tam, J.P. Proc. Natl. Acad. Sci. U.S.A. 1988, 55, 5409; Defoort, J.P.; Nardelli, B;. Huang, W.; Ho, D.; Tam, J.P. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 3879; Nardelli, B.; Lu, Y.A.; Shiu, D.R.; Dalpieire-Defoort, C.; Profy, A.T.; Tam, J.P. J. Immun. 1992, 148, 914; Tam, J.P.; Clavijo, P.; Lu, Y.A.; Nussenzweig, V.; Nussenzweig, R.; Zavala, F. J. Exp. Med. 1990, 171, 299.
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    • 5. Tam, J.P. Proc. Natl. Acad. Sci. U.S.A. 1988, 55, 5409; Defoort, J.P.; Nardelli, B;. Huang, W.; Ho, D.; Tam, J.P. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 3879; Nardelli, B.; Lu, Y.A.; Shiu, D.R.; Dalpieire-Defoort, C.; Profy, A.T.; Tam, J.P. J. Immun. 1992, 148, 914; Tam, J.P.; Clavijo, P.; Lu, Y.A.; Nussenzweig, V.; Nussenzweig, R.; Zavala, F. J. Exp. Med. 1990, 171, 299.
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    • 6. Adamantane skeleton functionalized with activated carboxylate groups at 1,3-bridge head positions appeared particularly attractive for supporting dendrons because of the anticipation that these centers would, not only provide most appropriate geometry to mimic a tetrahedral nucleus but the amide side chains carrying dendrons would, in most likelihood prefer to adopt an anti conformation (Karle, I.; Ranganathan D.; Haridas, V. J. Am. Chem. Soc. 1996, 118, 10916; Ranganathan, D.; Haridas, V.; Madhusudanan K. P.; Roy, R.; Nagaraj, R.; John, G. B.; Sukhaswami, M. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1105) particularly suitable for attaining globular conformation.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 10916
    • Karle, I.1    Ranganathan, D.2    Haridas, V.3
  • 17
    • 0029843729 scopus 로고    scopus 로고
    • 6. Adamantane skeleton functionalized with activated carboxylate groups at 1,3-bridge head positions appeared particularly attractive for supporting dendrons because of the anticipation that these centers would, not only provide most appropriate geometry to mimic a tetrahedral nucleus but the amide side chains carrying dendrons would, in most likelihood prefer to adopt an anti conformation (Karle, I.; Ranganathan D.; Haridas, V. J. Am. Chem. Soc. 1996, 118, 10916; Ranganathan, D.; Haridas, V.; Madhusudanan K. P.; Roy, R.; Nagaraj, R.; John, G. B.; Sukhaswami, M. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1105) particularly suitable for attaining globular conformation.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1105
    • Ranganathan, D.1    Haridas, V.2    Madhusudanan K, P.3    Roy, R.4    Nagaraj, R.5    John, G.B.6    Sukhaswami, M.B.7
  • 18
    • 0011429195 scopus 로고    scopus 로고
    • 4, containing seven chiral centers and eight terminal carbomethoxy groups, in excellent yields. Vapour pressure osmometry experiments conducted with 4mM and 40mM solutions of hexadeca carboxylic acid (sticky solid) of 3b showed that it remains as a monomeric entity in aqueous solution
    • 4, containing seven chiral centers and eight terminal carbomethoxy groups, in excellent yields. Vapour pressure osmometry experiments conducted with 4mM and 40mM solutions of hexadeca carboxylic acid (sticky solid) of 3b showed that it remains as a monomeric entity in aqueous solution.
  • 19
    • 0011382399 scopus 로고    scopus 로고
    • note
    • +.
  • 20
    • 0011475858 scopus 로고    scopus 로고
    • note
    • 2O mixture as a function of time.
  • 21
    • 0011476996 scopus 로고    scopus 로고
    • The models for Glu scaffoldings were generated using Biosym version 2.3.5 package on a Silicon Graphics IRIS Crimson Elan Work station. The energy minimization was done with INSIGHT and DISCOVER program packages (Biosym Technologies, San Diego, CA), using CVFF force field
    • 10. The models for Glu scaffoldings were generated using Biosym version 2.3.5 package on a Silicon Graphics IRIS Crimson Elan Work station. The energy minimization was done with INSIGHT and DISCOVER program packages (Biosym Technologies, San Diego, CA), using CVFF force field.


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