Anion recognition by cyclic peptides.

Anion binding selectivity can often be controlled by judicious arrangement of recognition moieties around an anion of interest. Indeed, nature takes advantage of large peptides/proteins to provide highly efficient and selective anion receptors using a small number of amino acid building blocks placed in a precise arrangement. Cyclic peptides are ideal synthetic scaffolds to position binding residues in a similarly preorganised manner as their synthetic versatility and rigidified structure allows precise control over their size and shape. This review summarises the recent use of such cyclic peptide scaffolds as receptors for various anionic species.

[1]  R. Goddard,et al.  A New Cyclic Pseudopeptide Composed of (l)-Proline and 3-Aminobenzoic Acid Subunits as a Ditopic Receptor for the Simultaneous Complexation of Cations and Anions , 1999 .

[2]  Jin‐Pei Cheng,et al.  Effective receptors for fluoride and acetate ions : synthesis and binding study of pyrrole-and cystine-based cyclopeptido-mimetics , 2007 .

[3]  K. Jolliffe,et al.  Selective anion binding in water with use of a zinc(II) dipicolylamino functionalized diketopiperazine scaffold. , 2009, The Journal of organic chemistry.

[4]  P. Beer,et al.  Sulfate anion templation of macrocycles, capsules, interpenetrated and interlocked structures. , 2009, Chemical Society reviews.

[5]  Philip A. Gale,et al.  Synthetic transporters for sulfate: a new method for the direct detection of lipid bilayer sulfate transport , 2014 .

[6]  H. Ishida,et al.  Highly Effective Binding of Phosphomonoester with Neutral Cyclic Peptides which Include a Non-natural Amino Acid , 1995 .

[7]  K. Jolliffe,et al.  Bis[zinc(II)dipicolylamino]-functionalised peptides as high affinity receptors for pyrophosphate ions in water. , 2013, Chemical communications.

[8]  J. Rebek,et al.  Improved synthesis of functionalized molecular platforms related to marine cyclopeptides. , 2001 .

[9]  K. Jolliffe,et al.  Neutral cryptand-like cyclic peptide–thiourea receptors for selective recognition of sulphate anions in aqueous solvents , 2012 .

[10]  D. Nolting,et al.  A Cyclic Hexapeptide Containing L-Proline and 6-Aminopicolinic Acid Subunits Binds Anions in Water. , 2001, Angewandte Chemie.

[11]  B. Hay,et al.  Influence of linker structure on the anion binding affinity of biscyclopeptides , 2007 .

[12]  Hai‐Yu Hu,et al.  A new fluorescent chemosensor for anion based on an artificial cyclic tetrapeptide , 2006 .

[13]  T. Chakraborty,et al.  Cyclic trimer of 5-(aminomethyl)-2-furancarboxylic acid as a novel synthetic receptor for carboxylate recognition , 2002 .

[14]  G. Haberhauer,et al.  Molecular scaffold for the construction of three-armed and cage-like receptors. , 2005, Chemistry.

[15]  K. Jolliffe,et al.  Sulfate-selective recognition by using neutral dipeptide anion receptors in aqueous solution. , 2014, Chemistry.

[16]  T. Gunnlaugsson,et al.  Synthesis, photophysical and NMR evaluations of thiourea-based anion receptors possessing an acetamide moiety , 2010 .

[17]  Kwang S. Kim,et al.  NOVEL AMPHI-IONOPHORES , 1998 .

[18]  R. Goddard,et al.  Fine Tuning of the Cation Affinity of Artificial Receptors Based on Cyclic Peptides by Intramolecular Conformational Control , 2001 .

[19]  Ana M. Belenguer,et al.  Dynamic combinatorial development of a neutral synthetic receptor that binds sulfate with nanomolar affinity in aqueous solution. , 2011, Chemical communications.

[20]  Jin‐Pei Cheng,et al.  A cystine-bearing pseudo-cyclopeptide as a new amphi-receptor , 2002 .

[21]  R. Goddard,et al.  A cyclopeptide-derived molecular cage for sulfate ions that closes with a click. , 2010, Chemistry.

[22]  Cally J E Haynes,et al.  Anion receptor chemistry: highlights from 2011 and 2012. , 2014, Chemical Society reviews.

[23]  M. Sokabe,et al.  Synthesis and Ion Channel Formation of Novel Cyclic Peptides Containing a Non-natural Amino Acid , 1997 .

[24]  K. Jolliffe,et al.  Selective recognition of sulfate ions by tripodal cyclic peptides functionalised with (thio)urea binding sites. , 2012, Organic & biomolecular chemistry.

[25]  R. Goddard,et al.  Intramolecular conformational control in a cyclic peptide composed of alternating L-proline and substituted 3-aminobenzoic acid subunits , 2000 .

[26]  J. Turnay,et al.  Annexin-Phospholipid Interactions. Functional Implications , 2013, International journal of molecular sciences.

[27]  I. Karle,et al.  Cystinophanes, a Novel Family of Aromatic-Bridged Cystine Cyclic Peptides: Synthesis, Crystal Structure, Molecular Recognition, and Conformational Studies , 1998 .

[28]  P. Beer,et al.  Sulfate selective anion recognition by a novel tetra-imidazolium zinc metalloporphyrin receptor. , 2006, Dalton transactions.

[29]  G. Haberhauer,et al.  Syntheses and Structures of Imidazole Analogues of Lissoclinum Cyclopeptides , 2003 .

[30]  S. Luis,et al.  Efficient synthesis of pseudopeptidic molecular cages. , 2012, Chemistry.

[31]  R. Goddard,et al.  Formation of a cyclic tetrapeptide mimic by thermal azide-alkyne 1,3-dipolar cycloaddition. , 2010, Chemical communications.

[32]  G. Haberhauer,et al.  Synthesis and Structural Investigation of C4‐ and C2‐Symmetric Molecular Scaffolds Based on Imidazole Peptides , 2007 .

[33]  D. Ranganathan,et al.  Cystine-based cyclic oligoureas: a new class of hydrogen-bonding electroneutral anion receptors , 2001 .

[34]  R. Goddard,et al.  Conformation and anion binding properties of cyclic hexapeptides containing l-4-hydroxyproline and 6-aminopicolinic acid subunits , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[35]  S. Luis,et al.  Supramolecular control for the modular synthesis of pseudopeptidic macrocycles through an anion-templated reaction. , 2008, Journal of the American Chemical Society.

[36]  R. Goddard,et al.  Anion-binding properties of a cyclic pseudohexapeptide containing 1,5-disubstituted 1,2,3-triazole subunits. , 2011, The Journal of organic chemistry.

[37]  S. Otto,et al.  Dynamic combinatorial optimization of a neutral receptor that binds inorganic anions in aqueous solution. , 2003, Journal of the American Chemical Society.

[38]  Philip A. Gale,et al.  From anion receptors to transporters. , 2011, Accounts of chemical research.

[39]  P. Ballester,et al.  A squaramide fluorescent ensemble for monitoring sulfate in water , 2001 .

[40]  S. Kubik.  Large Increase in Cation Binding Affinity of Artificial Cyclopeptide Receptors by an Allosteric Effect , 1999 .

[41]  S. Luis,et al.  Tight and selective caging of chloride ions by a pseudopeptidic host. , 2014, Chemistry.

[42]  S. Otto,et al.  Optimization of the binding properties of a synthetic anion receptor using rational and combinatorial strategies. , 2005, Biosensors & bioelectronics.

[43]  K. Jolliffe.  Backbone-modified Cyclic Peptides: New Scaffolds for Supramolecular Chemistry , 2005 .

[44]  W. Guo,et al.  Polymethylene-bridged Cystine–Glycine-containing Cyclopeptides as Hydrogen-bonding Electroneutral Anion Receptors: Design, Synthesis, and Halide Ion Recognition , 2004 .

[45]  Yi Pan,et al.  Squaramide-based tripodal receptors for selective recognition of sulfate anion. , 2013, Chemical communications.

[46]  P. Ballester,et al.  Evaluation of anion selectivity in protic media by squaramide-Cresol Red ensembles , 2004 .

[47]  G. Haberhauer,et al.  Anion Recognition by Neutral Macrocyclic Azole Amides , 2009 .

[48]  Philip A. Gale,et al.  Metal-organic anion receptors: trans-functionalised platinum complexes. , 2008, Chemical communications.

[49]  Youngdo Won,et al.  Novel amphi-ionophore in aqueous solution: Cyclohexaalanyl , 2002 .

[50]  Biao Wu,et al.  Sulfate Binding with a Tripodal Tris(4-pyridylurea) Receptor , 2013 .

[51]  K. Jolliffe,et al.  Tuning colourimetric indicator displacement assays for naked-eye sensing of pyrophosphate in aqueous media , 2013 .

[52]  S. Kubik.  Amino acid containing anion receptors. , 2009, Chemical Society reviews.

[53]  K. Jolliffe,et al.  Synthesis of a family of cyclic peptide-based anion receptors. , 2011, Organic & biomolecular chemistry.

[54]  I. Robina,et al.  Synthesis of a C3‐Symmetric Furyl‐Cyclopeptide Platform with Anion Recognition Properties , 2010 .

[55]  Luigi Fabbrizzi,et al.  Anion recognition by hydrogen bonding: urea-based receptors. , 2010, Chemical Society reviews.

[56]  Philip A. Gale,et al.  Anion transporters and biological systems. , 2013, Accounts of chemical research.

[57]  D. Nolting,et al.  A molecular oyster: a neutral anion receptor containing two cyclopeptide subunits with a remarkable sulfate affinity in aqueous solution. , 2002, Journal of the American Chemical Society.

[58]  Biao Wu,et al.  Selective anion sensing by a ruthenium(II)-bipyridyl-functionalized tripodal tris(urea) receptor. , 2012, Dalton transactions.

[59]  F A Quiocho,et al.  Atomic structures of periplasmic binding proteins and the high-affinity active transport systems in bacteria. , 1990, Philosophical transactions of the Royal Society of London. Series B, Biological sciences.

[60]  F A Quiocho,et al.  The 2 A resolution structure of the sulfate-binding protein involved in active transport in Salmonella typhimurium. , 1988, Journal of molecular biology.

[61]  E. Garcı́a-España,et al.  Selective recognition of sulfate anions by a cyclopeptide-derived receptor in aqueous phosphate buffer. , 2013, Organic letters.

[62]  L. Fabbrizzi,et al.  Anion recognition by coordinative interactions: metal-amine complexes as receptors. , 2013, Chemical Society reviews.

[63]  T. Gunnlaugsson,et al.  Selective and tuneable recognition of anions using C(3v)-symmetrical tripodal urea-amide receptor platforms. , 2011, Chemical communications.

[64]  Dan Yang,et al.  Cyclic Hexapeptide of d,l-α-Aminoxy Acids as a Selective Receptor for Chloride Ion , 2002 .

[65]  R. Srinivas,et al.  Self-assembling cyclic tetrapeptide from alternating C-linked carbo-beta-amino acid [(S)-beta-Caa] and alpha-aminoxy acid [(R)-Ama]: a selective chloride ion receptor. , 2010, The Journal of organic chemistry.

[66]  S. Luis,et al.  Tuning chloride binding, encapsulation, and transport by peripheral substitution of pseudopeptidic tripodal small cages. , 2012, Chemistry.

[67]  D. Mink,et al.  Natural products analogs as scaffolds for supramolecular and combinatorial chemistry , 1998 .

[68]  S. Kubik,et al.  Selective sensing of sulfate in aqueous solution using a fluorescent bis(cyclopeptide). , 2007, Organic letters.

[69]  A. Reynolds,et al.  Selective recognition of pyrophosphate in water using a backbone modified cyclic peptide receptor. , 2006, Chemical communications.

[70]  J. Riordan.  Arginyl residues and anion binding sites in proteins , 1979, Molecular and Cellular Biochemistry.

[71]  P. Kolandaivel,et al.  Structural Properties and Anion Binding Affinity of cyclo[(1R,3S)-γ-Acc-Gly]3 Hexapeptide , 2009 .

[72]  Molecular design and synthesis of artificial ion channels based on cyclic peptides containing unnatural amino acids. , 2001, The Journal of organic chemistry.

[73]  P. Ballester,et al.  Squaramido-based receptors: Molecular recognition of carboxylate anions in highly competitive media , 1998 .

[74]  K. Jolliffe,et al.  Selective pyrophosphate recognition by cyclic peptide receptors in physiological saline. , 2012, Chemistry, an Asian journal.

[75]  S. Otto,et al.  Noncovalent interactions within a synthetic receptor can reinforce guest binding. , 2006, Journal of the American Chemical Society.

[76]  F. Wang,et al.  Anion complexation and sensing using modified urea and thiourea-based receptors. , 2010, Chemical Society reviews.

[77]  Thorfinnur Gunnlaugsson,et al.  Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors. , 2010, Chemical Society reviews.

[78]  R. Custelcean.  Urea-functionalized crystalline capsules for recognition and separation of tetrahedral oxoanions. , 2013, Chemical communications.

[79]  P. Beer,et al.  Interlocked host molecules for anion recognition and sensing , 2013 .

[80]  J. Sessler,et al.  Receptors for tetrahedral oxyanions , 2006 .

[81]  Dan Yang,et al.  A Cyclic Hexapeptide Comprising Alternating α‐Aminoxy and α‐Amino Acids is a Selective Chloride Ion Receptor , 2005 .

[82]  H. Ishida,et al.  Serine proteinases mimics: hydrolytic activity of cyclic peptides which include a non-natural amino acid , 1995 .

[83]  A. Reynolds,et al.  Synthesis of backbone modified cyclic peptides bearing dipicolylamino sidearms , 2011 .

[84]  K. Jolliffe,et al.  Hybrid cyclic peptide-thiourea cryptands for anion recognition. , 2011, Chemical communications.

[85]  F. Quiocho,et al.  Modulation of a salt link does not affect binding of phosphate to its specific active transport receptor. , 1996, Biochemistry.