Parallel Synthesis of Polystyrene Anchored Imine Sulfide Materials: Sorption and Metal Sensing Studies

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Abstract

Se reporta la síntesis de una biblioteca combinatorial de 30 N-derivados fenil etilo (nitro, aminas e iminas) unidos a una resina PS-tiofenol. La secuencia de 5 pasos de reacción fue seguida por ¹H RMN, EM y espectroscopia de fluorescencia de la resina. Las iminas fueron monitoreadas para aquellas que mostraron gran capacidad de porción para iones Cu(II) y Pb(II) y aquellas que mostraron un gran cambio de fluorescencia por la unión al metal.

Translated abstract

In the present work we report the synthesis of a combinatorial library of 30 phenyl-ethyl based N-derivatives [nitro, amines and imines] bound to PS-thiophenol resin. The five step reaction sequence was characterized by ¹H NMR, MS and fluorescence spectroscopy of resin beads. The imines were screened for those that exhibited a large sorption capacity for Cu(II) and Pb(II) ions and those exhibiting a large fluorescence change upon the metal binding.

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Most cited references 19

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Principles of Fluorescence Spectroscopy

Joseph R. Lakowicz (2006)

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High-throughput sequence determination of cyclic peptide library members by partial Edman degradation/mass spectrometry.

Dehua Pei, S-I Joo, Bhaskar Gopishetty … (2006)

Cyclic peptides provide attractive lead compounds for drug discovery and excellent molecular probes in biomedical research. Large combinatorial libraries of cyclic peptides can now be routinely synthesized by the split-and-pool method and screened against biological targets. However, post-screening sequence determination of hit peptides has been problematic. In this report, a high-throughput method for the sequence determination of cyclic peptide library members has been developed. TentaGel microbeads (90 mum) were spatially segregated into outer and inner layers; cyclic peptides were displayed on the bead surface, whereas the inner core of each bead contained the corresponding linear peptide as the encoding sequence. After screening of the cyclic peptide library against a macromolecular target, the identity of hit peptides was determined by sequencing the linear encoding peptides inside the bead using a partial Edman degradation/mass spectrometry method. On-bead screening of an octapeptide library (theoretical diversity of 160 000) identified cyclic peptides that bind to streptavidin. A 400-member library of tyrocidine A analogues was synthesized on TentaGel macrobeads and solution-phase screening of the library directly against bacterial cells identified a tyrocidine analogue of improved antibacterial activity. Our results demonstrate that the new method for cyclic peptide sequence determination is reliable, operationally simple, rapid, and inexpensive and should greatly expand the utility of cyclic peptides in biomedical research.