Literature DB >> 22360622

Enhanced shape-selective recognition of anion guests through complexation-induced organization of porphyrin hosts.

MariJo Wienkers1, Josmalen Ramos, Hikma Jemal, Chaz Cardenas, Paul Wiget, Alfreda Nelson, Shiloh Free, Jun Wu, Rebecca Roach, Marius Vulcan, Kristopher Waynant, Kyle Fort, Anna Vladimirova, Jeffery Sun, Samuel Eli Hunt, Dmitry M Rudkevich, Stephen D Starnes.   

Abstract

We present a fortuitous discovery of enhanced shape-selective recognition of anion guests that stems from a complexation-induced conformational change in porphyrin hosts upon anion binding. Porphyrin hosts reported here exist in a conformation that is not favorable to guest binding. Anions that bind strongly are those that can induce a conformational change in the host to allow guest binding. Furthermore, guests that mimic the shape of the newly formed pocket bind the strongest.

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Year:  2012        PMID： 22360622      PMCID： PMC3313493          DOI： 10.1021/ol203249x

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

Review 1.  Anion recognition: synthetic receptors for anions and their application in sensors.

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3.  Facilitated phosphatidylserine flip-flop across vesicle and cell membranes using urea-derived synthetic translocases.

Authors:  Yoshihiro Sasaki; Rameshwer Shukla; Bradley D Smith
Journal:  Org Biomol Chem       Date:  2003-12-10       Impact factor: 3.876

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Authors:  Chomchai Suksai; Thawatchai Tuntulani
Journal:  Chem Soc Rev       Date:  2003-07       Impact factor: 54.564

5.  Structural criteria for the rational design of selective ligands: convergent hydrogen bonding sites for the nitrate anion.

Authors:  Benjamin P Hay; Maciej Gutowski; David A Dixon; Jorge Garza; Rubicelia Vargas; Bruce A Moyer
Journal:  J Am Chem Soc       Date:  2004-06-30       Impact factor: 15.419

6.  An induced fit conformational change underlies the binding mechanism of the heme transport proteobacteria-protein HemS.

Authors:  Sabine Schneider; Katherine H Sharp; Paul D Barker; Max Paoli
Journal:  J Biol Chem       Date:  2006-08-30       Impact factor: 5.157

7.  Fluorescent 'twist-on' sensing by induced-fit anion stabilisation of a planar chromophore.

Authors:  Adam N Swinburne; Martin J Paterson; Andrew Beeby; Jonathan W Steed
Journal:  Chemistry       Date:  2010-03-01       Impact factor: 5.236

Review 8.  Desperately seeking sensors.

Authors:  A W Czarnik
Journal:  Chem Biol       Date:  1995-07

9.  Discovery of linear receptors for multiple dihydrogen phosphate ions using dynamic combinatorial chemistry.

Authors:  Sophie R Beeren; Jeremy K M Sanders
Journal:  J Am Chem Soc       Date:  2011-02-28       Impact factor: 15.419

10.  Determination of inorganic phosphate in serum and saliva using a synthetic receptor.

Authors:  Suzanne L Tobey; Eric V Anslyn
Journal:  Org Lett       Date:  2003-06-12       Impact factor: 6.005
  10 in total

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