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Volumn 7, Issue 1, 2005, Pages 78-84

A convenient orthogonally cleavable methionine handle for anchoring amines to polymeric supports

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINE; METHIONINE; PEPTIDE; POLYMER; PROTEIN;

EID: 13544267665     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc049949y     Document Type: Article
Times cited : (4)

References (48)
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    • To the best of our knowledge, the first application of CNBr chemistry to effect cleavage in solid-phase synthesis was the ingenious contribution of (a) Hancock, W. S.; Marshall, G. R. J. Am. Chem. Soc. 1975, 97, 7488-7489. A subsequent enzymatic step removes the C-terminal Hsl to provide the wanted C-terminal residue. More recently, elegant applications of CNBr cleavage have been made for combinatorial chemistry: (b) Youngquist, R. S.; Fuentes, G. R.; Lacey, M. P.; Keough, T. J. Am. Chem. Soc. 1995, 117, 3900-3906. (c) Davies, M.; Bradley, M. Tetrahedron Lett. 1997, 38, 8565-8568. (d) Ko, D.-H.; Kim, D. J.; Lyu, C. S.; Min, I. K.; Moon, H. Tetrahedron Lett. 1998, 39, 297-300. (e) Franz, A. H.; Liu, R.; Song, A.; Lam, K. S.; Lebrilla, C. B. J. Comb. Chem. 2003, 5, 125-137. (f) Pastor, J. J.; Lingard, I.; Bhalay, G.; Bradley, M. J. Comb. Chem. 2003, 5, 85-90. (g) Song, A.; Zhang, J.; Lebrilla, C. B.; Lam, K. S. J. Am. Chem. Soc. 2003, 125, 6180-6188.
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    • To the best of our knowledge, the first application of CNBr chemistry to effect cleavage in solid-phase synthesis was the ingenious contribution of (a) Hancock, W. S.; Marshall, G. R. J. Am. Chem. Soc. 1975, 97, 7488-7489. A subsequent enzymatic step removes the C-terminal Hsl to provide the wanted C-terminal residue. More recently, elegant applications of CNBr cleavage have been made for combinatorial chemistry: (b) Youngquist, R. S.; Fuentes, G. R.; Lacey, M. P.; Keough, T. J. Am. Chem. Soc. 1995, 117, 3900-3906. (c) Davies, M.; Bradley, M. Tetrahedron Lett. 1997, 38, 8565-8568. (d) Ko, D.-H.; Kim, D. J.; Lyu, C. S.; Min, I. K.; Moon, H. Tetrahedron Lett. 1998, 39, 297-300. (e) Franz, A. H.; Liu, R.; Song, A.; Lam, K. S.; Lebrilla, C. B. J. Comb. Chem. 2003, 5, 125-137. (f) Pastor, J. J.; Lingard, I.; Bhalay, G.; Bradley, M. J. Comb. Chem. 2003, 5, 85-90. (g) Song, A.; Zhang, J.; Lebrilla, C. B.; Lam, K. S. J. Am. Chem. Soc. 2003, 125, 6180-6188.
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    • To the best of our knowledge, the first application of CNBr chemistry to effect cleavage in solid-phase synthesis was the ingenious contribution of (a) Hancock, W. S.; Marshall, G. R. J. Am. Chem. Soc. 1975, 97, 7488-7489. A subsequent enzymatic step removes the C-terminal Hsl to provide the wanted C-terminal residue. More recently, elegant applications of CNBr cleavage have been made for combinatorial chemistry: (b) Youngquist, R. S.; Fuentes, G. R.; Lacey, M. P.; Keough, T. J. Am. Chem. Soc. 1995, 117, 3900-3906. (c) Davies, M.; Bradley, M. Tetrahedron Lett. 1997, 38, 8565-8568. (d) Ko, D.-H.; Kim, D. J.; Lyu, C. S.; Min, I. K.; Moon, H. Tetrahedron Lett. 1998, 39, 297-300. (e) Franz, A. H.; Liu, R.; Song, A.; Lam, K. S.; Lebrilla, C. B. J. Comb. Chem. 2003, 5, 125-137. (f) Pastor, J. J.; Lingard, I.; Bhalay, G.; Bradley, M. J. Comb. Chem. 2003, 5, 85-90. (g) Song, A.; Zhang, J.; Lebrilla, C. B.; Lam, K. S. J. Am. Chem. Soc. 2003, 125, 6180-6188.
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    • 0038485518 scopus 로고    scopus 로고
    • To the best of our knowledge, the first application of CNBr chemistry to effect cleavage in solid-phase synthesis was the ingenious contribution of (a) Hancock, W. S.; Marshall, G. R. J. Am. Chem. Soc. 1975, 97, 7488-7489. A subsequent enzymatic step removes the C-terminal Hsl to provide the wanted C-terminal residue. More recently, elegant applications of CNBr cleavage have been made for combinatorial chemistry: (b) Youngquist, R. S.; Fuentes, G. R.; Lacey, M. P.; Keough, T. J. Am. Chem. Soc. 1995, 117, 3900-3906. (c) Davies, M.; Bradley, M. Tetrahedron Lett. 1997, 38, 8565-8568. (d) Ko, D.-H.; Kim, D. J.; Lyu, C. S.; Min, I. K.; Moon, H. Tetrahedron Lett. 1998, 39, 297-300. (e) Franz, A. H.; Liu, R.; Song, A.; Lam, K. S.; Lebrilla, C. B. J. Comb. Chem. 2003, 5, 125-137. (f) Pastor, J. J.; Lingard, I.; Bhalay, G.; Bradley, M. J. Comb. Chem. 2003, 5, 85-90. (g) Song, A.; Zhang, J.; Lebrilla, C. B.; Lam, K. S. J. Am. Chem. Soc. 2003, 125, 6180-6188.
    • (2003) J. Comb. Chem. , vol.5 , pp. 125-137
    • Franz, A.H.1    Liu, R.2    Song, A.3    Lam, K.S.4    Lebrilla, C.B.5
  • 14
    • 0038526311 scopus 로고    scopus 로고
    • To the best of our knowledge, the first application of CNBr chemistry to effect cleavage in solid-phase synthesis was the ingenious contribution of (a) Hancock, W. S.; Marshall, G. R. J. Am. Chem. Soc. 1975, 97, 7488-7489. A subsequent enzymatic step removes the C-terminal Hsl to provide the wanted C-terminal residue. More recently, elegant applications of CNBr cleavage have been made for combinatorial chemistry: (b) Youngquist, R. S.; Fuentes, G. R.; Lacey, M. P.; Keough, T. J. Am. Chem. Soc. 1995, 117, 3900-3906. (c) Davies, M.; Bradley, M. Tetrahedron Lett. 1997, 38, 8565-8568. (d) Ko, D.-H.; Kim, D. J.; Lyu, C. S.; Min, I. K.; Moon, H. Tetrahedron Lett. 1998, 39, 297-300. (e) Franz, A. H.; Liu, R.; Song, A.; Lam, K. S.; Lebrilla, C. B. J. Comb. Chem. 2003, 5, 125-137. (f) Pastor, J. J.; Lingard, I.; Bhalay, G.; Bradley, M. J. Comb. Chem. 2003, 5, 85-90. (g) Song, A.; Zhang, J.; Lebrilla, C. B.; Lam, K. S. J. Am. Chem. Soc. 2003, 125, 6180-6188.
    • (2003) J. Comb. Chem. , vol.5 , pp. 85-90
    • Pastor, J.J.1    Lingard, I.2    Bhalay, G.3    Bradley, M.4
  • 15
    • 0037951325 scopus 로고    scopus 로고
    • To the best of our knowledge, the first application of CNBr chemistry to effect cleavage in solid-phase synthesis was the ingenious contribution of (a) Hancock, W. S.; Marshall, G. R. J. Am. Chem. Soc. 1975, 97, 7488-7489. A subsequent enzymatic step removes the C-terminal Hsl to provide the wanted C-terminal residue. More recently, elegant applications of CNBr cleavage have been made for combinatorial chemistry: (b) Youngquist, R. S.; Fuentes, G. R.; Lacey, M. P.; Keough, T. J. Am. Chem. Soc. 1995, 117, 3900-3906. (c) Davies, M.; Bradley, M. Tetrahedron Lett. 1997, 38, 8565-8568. (d) Ko, D.-H.; Kim, D. J.; Lyu, C. S.; Min, I. K.; Moon, H. Tetrahedron Lett. 1998, 39, 297-300. (e) Franz, A. H.; Liu, R.; Song, A.; Lam, K. S.; Lebrilla, C. B. J. Comb. Chem. 2003, 5, 125-137. (f) Pastor, J. J.; Lingard, I.; Bhalay, G.; Bradley, M. J. Comb. Chem. 2003, 5, 85-90. (g) Song, A.; Zhang, J.; Lebrilla, C. B.; Lam, K. S. J. Am. Chem. Soc. 2003, 125, 6180-6188.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 6180-6188
    • Song, A.1    Zhang, J.2    Lebrilla, C.B.3    Lam, K.S.4


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