Transfer of chirality for memory and separation

Topics in Current Chemistry

Volumn 298, Issue , 2011, Pages 143-188

  Lauceri, Rosaria ^a   D'Urso, Alessandro ^b   Mammana, Angela ^b   Purrello, Roberto ^b  

^a CNR   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

Author keywords

Hierarchy; Memory; Porphyrin; Supramolecular chirality; Transfer

Indexed keywords

PHENYLALANINE; POLYGLUTAMIC ACID; PORPHYRIN;

ARTICLE; BIOGENESIS; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; STEREOISOMERISM; THERMODYNAMICS;

BIOGENESIS; CIRCULAR DICHROISM; MODELS, MOLECULAR; PHENYLALANINE; POLYGLUTAMIC ACID; PORPHYRINS; STEREOISOMERISM; THERMODYNAMICS;

EID: 79951840459     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128_2010_87     Document Type: Article

References (71)

1. Simpson GJ (2004) Molecular origin of the remarkable chiral sensitivity of second-order nonlinear optics. Chem Phys Chem 5:1301-1310
2. Purrello R (2003) Lasting chiral memory. Nat Mater 2:216-217
3. Mukhopadhyay P, Wipf P, Beratan DN (2009) Optical signatures of molecular dissymmetry: combining theory with experiments to address stereochemical puzzles. Acc Chem Res 42:809-819
4. Simpson GJ (2004) Molecular origin of the remar (Pubitemid 40886432)
5. D'Urso A, Mammana A, Balaz M et al (2009) Interactions of a tetra-anionic porphyrin with DNA: from a Z-DNA sensor to a versatile supramolecular device. J Am Chem Soc 131:2046-2047
6. Onouchi H, Miyagawa T, Morino K et al (2006) Assisted formation of chiral porphyrin homoaggregates by an induced helical poly(phenylacetylene) template and their chiral memory. Angew Chem Int Ed Engl 45:2381-2384 (Pubitemid 44105113)
7. Jiang S, Zhang L, Liu M (2009) Photo-triggered J-aggregation and chiral symmetry breaking of an anionic porphyrin (TPPS) in mixed organic solvent. Chem Commun 41:6252-6254
8. Zhang L, Liu M (2009) Supramolecular chirality and chiral inversion of tetraphenylsulfonato porphyrin assemblies on optically active polylysine. J Phys Chem B 113:14015-14020
9. Zhao L, Wang X, Li Y et al (2009) Chiral micelles of achiral TPPS and diblock copolymer induced by amino acids. Macromolecules 42:6253-6260
10. Micali N, Villari V, Castriciano M et al (2006) From fractal to nanorod porphyrin J-aggre-gates. Concentration-induced tuning of the aggregate size. J Phys Chem B 110:8289-8295
11. Jiang S, Liu M (2004) Aggregation and induced chirality of an anionic meso-tetraphenylsul-fonato porphyrin (TPPS) on a layer-by-layer assembled DNA/PAH matrix. J Phys Chem B 108:2880-2884
12. 2: phosphonium cationic porphyrins and the importance of the charge. J Photo-chem Photobiol B-Biol 57:51-59
13. Pasternack RF (2003) Circular dichroism and the interactions of water soluble porphyrins with DNA - a minireview. Chirality 15:329-332 (Pubitemid 36459439)
14. Palmans ARA, Meijer EW (2007) Amplification of chirality in dynamic supramolecular aggregates. Angew Chem Int Ed Engl 46:2-23
15. Kubat P, Lang K, Kral V et al (2002) Preprogramming of porphyrin-nucleic acid assemblies via variation of the alkyl/aryl substituents of phosphonium tetratolylporphyrins. J Phys Chem B 106:6784-6792 (Pubitemid 35281762)
16. Pasternack RF, Gurrieri S, Lauceri R et al (1996) Single-stranded nucleic acids as templates for porphyrin assembly formation. Inorg Chim Acta 246:7-12 (Pubitemid 126320389)
17. Kuciauskas D, Caputo GA (2009) Self-assembly of peptide-porphyrin complexes leads to pH-dependent excitonic coupling. J Phys Chem B 113:14439-14447
18. Kokona B, Kim AM, Roden RC et al (2009) Self assembly of coiled-coil peptide-porphyrin complexes. Biomacromolecules 10:1454-1459
19. De Luca G, Romeo A, Monsu Scolaro L et al (2010) Conformations of a model protein revealed by an aggregating CuII porphyrin: sensing the difference. Chem Commun 46:389-391
20. Monsu Scolaro L, Romeo A, Pasternack RF (2004) Tuning porphyrin/DNA supramolecular assemblies by competitive binding. J Am Chem Soc 126:7178-7179 (Pubitemid 38747759)
21. Pasternack RF, Giannetto A, Pagano P et al (1991) Self-assembly of porphyrins on nucleic acids and polypeptides. J Am Chem Soc 113:7799-7800
22. Purrello R, Gurrieri S, Lauceri R (1999) Porphyrin assemblies as chemical sensors. Coord Chem Rev 190-192:683-706
23. Purrello R, Bellacchio E, Gurrieri S et al (1998) pH modulation of porphyrins self-assembly onto polylysine. J Phys Chem B 102:8852-8857 (Pubitemid 128611842)
24. Lauceri R, Campagna T, Contino A et al (1996) Poly(A A U) triple helix formation promoted by porphyrin assembly. Angew Chem Int Ed Engl 35:215-216
25. Bustamante C, Gurrieri S, Pasternack RF et al (1994) Interaction of water-soluble porphyrins with single- and double-stranded polyribonucleotides. Biopolymers 34:1099-1104
26. Purrello R, Monsu Scolaro L, Bellacchio E et al (1998) Chiral H- and J-type aggregates of meso-tetrakis(4-sulfonatophenyl)porphine on a-helical polyglutamic acid induced by cationic porphyrins. Inorg Chem 37:3647-3648
27. Fleischer EB, Palmer JM, Srivastava TS et al (1971) Thermodyamic and kinetic properties of an iron-porphyrin system. J Am Chem Soc 93:3162-3167
28. Ribo JM, Crusats J, Farrera J-A et al (1994) Aggregation in water solutions of tetrasodium diprotonated meso-tetrakis(4-sulfonatophenyl)porphyrin. J Chem Soc, Chem Commun 6:681-682
29. Pasternack RF, Schaefer KF, Hambright P (1994) Resonance light-scattering studies of porphyrin diacid aggregates. Inorg Chem 33:2062-2065
30. Shimidzu T, Tomokazu I (1981) Accordion-type aggregate of water-soluble meso-tetraphe-nylporphyrin derivatives. Chem Lett 10:853-856
31. Ojadi E, Selzer R, Linschitz H (1985) Properties of porphyrin dimers, formed by pairing cationic and anionic porphyrins. J Am Chem Soc 107:7783-7784
32. Hofstra U, Koehorst RBM, Schaafsma TJ (1986) Excited-state properties of water-soluble porphyrin dimmers. Chem Phys Lett 130:555-559
33. 0-tetrapyridin-4-yl porphyr-ins, their N-methylated tetracations, and heterodimers with ms-tetraphenylsulfonato porphyr-ins. J Am Chem Soc 118:6671-6680 (Pubitemid 26248164)
34. Mukundam NE, Pethö G, Dixon D et al (1994) Interactions of an electron-rich tetracationic tentacle porphyrin with calf thymus DNA. Inorg Chem 33:4676-4687
35. Schneider H-J, Wang M (1994) DNA interactions with porphyrins bearing ammonium side chains. J Org Chem 59:7473-7478
36. Lauceri R, Gurrieri S, Bellacchio E et al (2000) J-type aggregates of the anionic meso-tetrakis (4-sulfonatophenyl)porphine induced by "hindered" cationic porphyrins. Supramol Chem 12:193-202 (Pubitemid 33235770)
37. Bellacchio E, Lauceri R, Gurrieri S et al (1998) Template-imprinted chiral porphyrin aggregates. J Am Chem Soc 120:12353-12354
38. Purrello R, Raudino A, Monsù Scolaro L et al (2000) Ternary porphyrin aggregates and their chiral memory. J Phys Chem B 104:10900-10908 (Pubitemid 32023482)
39. Gibbs EJ, Tinoco I, Maestre M et al (1988) Self-assembly of porphyrins on nucleic acid templates. Biochem Biophys Res Commun 157:350-358 (Pubitemid 19004867)
40. Hunter CA, Sanders JKM (1990) The nature of p-p interactions. J Am Chem Soc 112: 5525-5534
41. Lauceri R, De Napoli M, Mammana A et al (2004) Hierarchical self-assembly of water-soluble porphyrins. Synth Met 147:49-55
42. Mammana A, De Napoli M, Lauceri R et al (2005) Induction and memory of chirality in porphyrin hetero-aggregates: the role of the central metal ion. Bioorg Med Chem 13: 5159-5163 (Pubitemid 41039975)
43. Geremia S, Di Costanzo L, Nardin G et al (2004) Assembly of positively charged porphyrins driven by metal ions: a novel polymeric arrangement of cationic metalloporphyrins. Inorg Chem 43:7579-7581
44. Lauceri R, Purrello R (2005) Transfer, memory and amplification of chirality in porphyrin aggregates. Supramol Chem 17:61-66
45. Lauceri R, D'urso A, Mammana A et al (2008) Chiral memory: induction, amplification, and switching in porphyrin assemblies. Chirality 20:411-419 (Pubitemid 351303981)
46. Lauceri R, Raudino A, Monsu' Scolaro L et al (2002) From achiral porphyrins to template-imprinted chiral aggregates and further. Self-replication of chiral memory from scratch. J Am Chem Soc 124:894-895 (Pubitemid 34130960)
47. Lauceri R, Fasciglione GF, D'Urso A et al (2008) Kinetic investigation of porphyrin interaction with chiral templates reveals unexpected features of the induction and self-propagation mechanism of chiral memory. J Am Chem Soc 130:10476-10477
48. Matassa R, Carbone M, Lauceri R et al (2007) Supramolecular structure of extrinsically chiral porphyrin hetero-assemblies and achiral analogues. Adv Mater 19:3961-3967 (Pubitemid 350190446)
49. Mammana A, D'Urso A, Lauceri R et al (2007) Switching off and on the supramolecular chiral memory in porphyrin assemblies. J Am Chem Soc 129:8062-8063 (Pubitemid 47035107)
50. Randazzo R, Lauceri R, Mammana A et al (2009) Interactions of L and D enantiomers of ruthenium(II) cationic complexes with achiral anionic porphyrins. Chirality 21:92-96
51. Randazzo R, Mammana A, D'Urso A et al (2008) Reversible "chiral memory" in ruthenium tris(phenanthroline)-anionic porphyrin complexes. Angew Chem Int Ed Engl 47:9879-9882
52. Balzani V, Juris A (2001) Photochemistry and photophysics of Ru(II)-polypyridine complexes in the Bologna group. From early studies to recent developments. Coord Chem Rev 21:97-115
53. 2TPPS complex. Chirality 19:642-646 (Pubitemid 47075993)
54. Amabilino DB (2007) Supramolecular assembly: nanofibre whirlpools. Nat Mater 6:924-925 (Pubitemid 350210564)
55. Kondepudi DK, Kaufman RJ, Singh N (1990) Chiral symmetry breaking in sodium chlorate crystallization. Science 250:975-976 (Pubitemid 120031800)
56. Ribo JM, Crusats J, Sague F et al (2001) Chiral sign induction by vortices during the formation of mesophases in stirred solutions. Science 292:2063-2066 (Pubitemid 32694379)
57. Dzwolak W, Loksztejn A, Galinka-Rakoczj A et al (2007) Conformational indeterminism in protein misfolding: chiral amplification on amyloidogenic pathway of insulin. J Am Chem Soc 129:7517-7522 (Pubitemid 46981913)
58. Ohno O, Kaizu Y, Kobayashi H (1993) J-aggregate formation of a water-soluble porphyrin in acidic aqueous media. J Chem Phys 99:4128-4139
59. Yamaguchi T, Kimura T, Matsuda H et al (2004) Macroscopic spinning chirality memorized in spin-coated films of spatially designed dendritic zinc porphyrin J-aggregates. Angew Chem Int Ed Engl 43:6350-6355 (Pubitemid 40029469)
60. Tsuda A, Akhtarul Alam Md, Harada T et al (2007) Spectroscopic visualization of vortex flows using dye-containing nanofibers. Angew Chem Int Ed Engl 46:8198-8202 (Pubitemid 350096597)
61. Wolffs M, George SJ, Tomovic Z et al (2007) Macroscopic origin of CD-effects by alignment of self-assembled fibers in solution. Angew Chem Int Ed Engl 46:8203-8205 (Pubitemid 350096598)
62. D'Urso A, Randazzo R, Lo Faro L et al (2010) Vortex and nanoscale chirality. Angew Chem Int Ed Engl 49:108-112
63. Spada GP (2008) Alignment by the convective and vortex flow of achiral self-assembled fibers induces strong circular dichroism effects. Angew Chem Int Ed Engl 47:636-638
64. Arteaga O, Canillas A, Purrello R et al (2009) Evidence of induced chirality in stirred solutions of supramolecular nanofibers. Opt Lett 34:2177-2179
65. Kostur M, Schindler M, Talkner P et al (2006) Chiral separation in microflows. Phys Rev Lett 96:014502-2-4
66. Pasternack RF, Huber PR, Boyd P et al (1972) Aggregation of meso-substituted water-soluble porphyrins. J Am Chem Soc 94:4511-4517
67. Akins DL, Zhu H-R, Guo C (1996) Aggregation of tetraaryl-substituted porphyrins in homogeneous solution. J Phys Chem 100:5420-5425 (Pubitemid 126790510)
68. Escudero C, Crusat J, Diez-Perez I et al (2006) Folding and hydrodynamic forces in J-aggregates of 5-phenyl-10,15,20-tris(4-sulfophenyl)porphyrin. Angew Chem Int Ed Engl 45:8032-8035 (Pubitemid 44912773)
69. Berova N, Nakanishi K (2000) In: Berova N, Nakanishi K, Woody RW (eds) Circular Dichroism, Principles and Applications. Wiley-VCH, Weinheim, pp 337-382
70. El-Hachemi Z, Escudero C, Arteaga O et al (2009) Chiral sign selection on the J-aggregates of diprotonated tetrakis-(4-sulfonatophenyl)porphyrin by traces of unidentified chiral contaminants present in the ultra-pure water used as solvent. Chirality 21:408-412
71. Escudero C, El-Hachemi Z, Crusats J et al (2005) Zwitterionic vs porphyrin free-base structures in 4-phenylsulfonic acid meso-substituted porphyrins. J Porphyr Phthalocyanines 9:852-863