Discovery of selective metal-binding peptoids using 19F encoded combinatorial libraries.
A method for encoding solid-phase split/mix combinatorial libraries using the chemical shift of synthetic fluoroarenes ('F-codes') has been developed. They have wide chemical shift dispersion and are detectable at the sub-micromol level. 19F NMR is used for decoding. Nine fluoroarenes bearing linkers for attachment to solid-phase synthesis supports through a photocleavable group were prepared. A library of 90 N-alkylglycines bearing substituted succinamides was prepared on solid phase from nine amines, in which the amine is encoded by the fluorinated tag, and 10 anhydrides. Metal binding studies followed by decoding identified unique, specific binders of copper(II) and iron(III) with microM K(D)s.
Pirrung
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MC
Department of Chemistry, Levine Science Research Center, Duke University, Durham, NC 27708-0317, USA. pirrung@chem.duke.edu
Park
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K
D000577:Amides / Q000737:chemistry; D000812:Anhydrides / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003300:Copper / Q000378:metabolism; D005462:Fluorine Radioisotopes; D005998:Glycine / Q000737:chemistry; D007501:Iron / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D018716:Molecular Mimicry; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D009942:Organometallic Compounds / Q000737:chemistry; D034444:Peptoids; D010777:Photochemistry; D013386:Succinates
D000577:Amides; D000812:Anhydrides; D005462:Fluorine Radioisotopes; D009842:Oligopeptides; D009942:Organometallic Compounds; D034444:Peptoids; D013386:Succinates; D003300:Copper; D007501:Iron; D005998:Glycine; C011116:succinamide