Combinatorial approach to selective multivalent ion pairing in mixed aqueous-organic media using bead-supported libraries of unnatural polyamines

Organic Letters

Volumn 4, Issue 1, 2002, Pages 31-34

  Manku, Sukhdev ^a   Hall, Dennis G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; AZO COMPOUND; COLORING AGENT; MICROSPHERE; NAPHTHALENESULFONIC ACID DERIVATIVE; POLYAMINE; WATER;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLUTION AND SOLUBILITY;

ANIONS; AZO COMPOUNDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLORING AGENTS; COMBINATORIAL CHEMISTRY TECHNIQUES; MICROSPHERES; NAPHTHALENESULFONATES; POLYAMINES; SOLUTIONS; WATER;

EID: 0037050521     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016827v     Document Type: Article

References (34)

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25. -1). Because of the hydrophobic nature of the polymer matrix it is possible that polyamine protonation is uniform mainly at the surface. This should not affect binding selectivity. Similarly, the hindered tritylamine anchor is not expected to interfere.
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27. N-Butyryl derivatives of D-α-amino acids were employed in order to distinguish them from the L-enantiomer and also to distinguish 4Acc from 2Acc by mass spectrometry.
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29. R at lower pH. Spermidine, with distant nitrogens spaced by 8 atoms, might be a more effective competitor of this spacer under these conditions.
30. Fielding, L. Tetrahedron 2000, 56, 6151.
31. 6 using standard methods described in ref 19 (see Supporting Information for more details). It should be noted that different binding stoichiometries may be possible on solid support as a result of the high local concentration of triamines within the beads.
32. Geometrical optimization was performed using the SYBYL force field on MacSpartan Plus version 1.1.9 (Wavefunction Inc.).
33. a values were determined using the 1:1 complexation model program developed by C. A. Hunter (see Supporting Information for more details).
34. R reaching the leftover sulfonate.