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Volumn 45, Issue 26, 2006, Pages 4277-4281

Sequence-dependent stereoselectivity in the binding of tetrapeptides in water by a flexible artificial receptor

Author keywords

Amino acids; Artificial peptide receptors; Combinatorial chemistry; Molecular recognition; Supramolecular chemistry

Indexed keywords

ARTIFICIAL TRISCATIONIC RECEPTORS; COMBINATORIAL LIBRARY; TETRAPEPTIDES;

EID: 33746310676     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601046     Document Type: Article
Times cited : (64)

References (33)
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    • For reviews on the early work of peptide recognition, see: a) H.-J. Schneider, Angew. Chem. 1993, 105, 890-892;
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    • Schneider, H.-J.1
  • 4
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    • For selected examples of oligopeptide binding in aqueous solvents based on metal-ligand interactions, see: a) A. T. Wright, E. V. Anslyn, Org. Lett. 2003, 5, 1341-1344;
    • (2003) Org. Lett. , vol.5 , pp. 1341-1344
    • Wright, A.T.1    Anslyn, E.V.2
  • 7
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    • For examples of peptide recognition based on hydrophobic interactions, see: a) C. Schmuck, M. Heil, ChemBioChem 2003, 4, 1232-1238;
    • (2003) ChemBioChem , vol.4 , pp. 1232-1238
    • Schmuck, C.1    Heil, M.2
  • 12
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    • For peptide recognition in water mainly based on electrostatic interactions, see: a) C. Schmuck, M. Heil, Chem. Eur. J. 2006, 12, 1339-1348;
    • (2006) Chem. Eur. J. , vol.12 , pp. 1339-1348
    • Schmuck, C.1    Heil, M.2
  • 14
    • 27844549490 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 7208-7212.
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 7208-7212
  • 22
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    • b) C. T. Walsh, Nature 2000, 406, 775-781;
    • (2000) Nature , vol.406 , pp. 775-781
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    • Angew. Chem. Int. Ed. 1999, 38, 1172-1193;
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  • 28
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    • note
    • We determined the necessary coupling conditions of the tert-butyl ester of D-Lac compared to normal amino acids by synthesis of a model peptide sequence on p-methyl-benzyldryl-amine (MBHA) resin. The free amino function of this resin was transformed with the help of Z-Glu(OtBu) into a carboxylate function allowing an analogous N to C solid-phase peptide-synthesis protocol like in the combinatorial library. The only difference is the higher acid sensitivity of the MBHA resin compared to TentaGel. It also allows the cleavage of the C-terminal tert-butyl esters with 50% TFA. In addition, the synthesized peptide can be cleaved with trifluoromethane sulfonic acid (TFMSA; 10% in TFA) and then analyzed with NMR spectroscopic techniques. These tests showed that it is possible to use the same conditions as those for like for amino acids to guarantee the quantitative coupling of D-Lac.
  • 30
    • 33746287120 scopus 로고    scopus 로고
    • note
    • However, the latter can not be used here as it does not swell in aqueous solutions and hence does not allow subsequent on-bead binding studies in water. For this purpose the hydrophilic TentaGel is the best choice.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.