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Synlett 2009(18): 2913-2918
DOI: 10.1055/s-0029-1218277
DOI: 10.1055/s-0029-1218277
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New YorkThieme Chemistry Journal Awardees - Where are They Now? Stabilisation of Porphyrins in Tetranucleotide-Bisporphyrin Arrays by Duplex Formation with Peptide Nucleic Acid
Further Information
Received
30 July 2009
Publication Date:
09 October 2009 (online)
Publication History
Publication Date:
09 October 2009 (online)

Abstract
UV irradiation of porphyrins in tetranucleotide-bisporphyrin arrays in organic solvents leads to selective bleaching of diphenyl porphyrins but not of tetraphenyl porphyrins. This was shown by absorbance and CD spectroscopy. The diphenyl porphyrin can be stabilised by duplex formation with a complementary PNA strand. These arrays are versatile building blocks for the synthesis of potential electronic arrays using a DNA scaffolding approach.
Key words
porphyrins - nucleotides - spectroscopy - supramolecular array
- 1a
Richert C.Meng M.Muller K.Heimann K. Small 2008, 4: 1040Reference Ris Wihthout Link - 1b
Wengel J. Org. Biomol. Chem. 2004, 2: 277Reference Ris Wihthout Link - 1c
Eckardt LH.Naumann K.Pankau WM.Rein M.Schweitzer M.Windhab N.von Kiedrowski G. Nature (London) 2002, 420: 286Reference Ris Wihthout Link - 1d
Seeman NC. Nature (London) 2003, 421: 427Reference Ris Wihthout Link - 1e
Turberfield A. Phys. World 2003, 16: 43Reference Ris Wihthout Link - 2a
Baumstark D.Wagenknecht HA. Chem. Eur. J. 2008, 14: 6640Reference Ris Wihthout Link - 2b
Wirges CT.Timper J.Fischler M.Sologubenko AS.Mayer J.Simon U.Carell T. Angew. Chem. Int. Ed. 2009, 48: 219Reference Ris Wihthout Link - 2c
Kumar TS.Madsen AS.Ostergaard ME.Sau SP.Wengel J.Hrdlicka PJ. J. Org. Chem. 2009, 74: 1070Reference Ris Wihthout Link - 2d
Jager S.Rasched G.Kornreich-Leshem H.Engeser M.Thum O.Famulok M. J. Am. Chem. Soc. 2005, 127: 15071Reference Ris Wihthout Link - 2e
Wagenknecht HA. Angew. Chem. Int. Ed. 2009, 48: 2838Reference Ris Wihthout Link - 3a
Hashmi SAN.Hu X.Immoos CE.Lee SJ.Grinstaff MW. Org. Lett. 2002, 4: 4571Reference Ris Wihthout Link - 3b
Kalek M.Madsen AS.Wengel J. J. Am. Chem. Soc. 2007, 129: 9392Reference Ris Wihthout Link - 3c
Immoos CE.Lee SJ.Grinstaff MW. J. Am. Chem. Soc. 2004, 126: 10814Reference Ris Wihthout Link - 4a
Grigorenko NA.Leumann CJ. Chem. Commun. 2008, 5417Reference Ris Wihthout Link - 4b
Bouquin N.Malinovskii VL.Guegano X.Liu SX.Decurtins S.Haner R. Chem. Eur. J. 2008, 14: 5732Reference Ris Wihthout Link - 4c
Tanaka K.Clever GH.Takezawa Y.Yamada Y.Kaul C.Shionoya M.Carell T. Nat. Nano. 2006, 1: 190Reference Ris Wihthout Link - 4d
Chelliserrykattil J.Lu H.Lee AHF.Kool ET. ChemBioChem 2008, 9: 2976Reference Ris Wihthout Link - 4e
Kool ET. Acc. Chem. Res. 2002, 35: 936Reference Ris Wihthout Link - 4f
Ahlborn C.Siegmund K.Richert C. J. Am. Chem. Soc. 2007, 129: 15218Reference Ris Wihthout Link - 4g
Takezawa Y.Maeda W.Tanaka K.Shionoya M. Angew. Chem. Int. Ed. 2009, 48: 1081Reference Ris Wihthout Link - 5
Bouamaied I.Nguyen T.Rühl T.Stulz E. Org. Biomol. Chem. 2008, 6: 3888 - 6
Fendt LA.Bouamaied I.Thöni S.Amiot N.Stulz E. J. Am. Chem. Soc. 2007, 129: 15319 - 7
Bouamaied I.Fendt LA.Wiesner M.Häussinger D.Thöni S.Amiot N.Stulz E. Nucleosides, Nucleotides Nucleic Acids 2007, 26: 1533 - 8
Bouamaied I.Fendt LA.Wiesner M.Häussinger D.Amiot N.Thöni S.Stulz E. Pure Appl. Chem. 2006, 78: 2003 - 9a
Suijkerbuijk B.Gebbink R. Angew. Chem. Int. Ed. 2008, 47: 7396Reference Ris Wihthout Link - 9b
Mullen KM.Gunter MJ. J. Org. Chem. 2008, 73: 3336Reference Ris Wihthout Link - 9c
Xie Y.Hill JP.Schumacher AL.Sandanayaka ASD.Araki Y.Karr PA.Labuta J.D’Souza F.Ito O.Anson CE.Powell AK.Ariga K. J. Phys. Chem. C 2008, 112: 10559Reference Ris Wihthout Link - 9d
D’Souza F.Maligaspe E.Zandler ME.Subbaiyan NK.Ohkubo K.Fukuzumi S. J. Am. Chem. Soc. 2008, 130: 16959Reference Ris Wihthout Link - 10
Nguyen T.Brewer A.Stulz E. Angew. Chem. Int. Ed. 2009, 48: 1974 - 11a
Mammana A.Asakawa T.Bitsch-Jensen K.Wolfe A.Chaturantabut S.Otani Y.Li XX.Li ZM.Nakanishi K.Balaz M.Ellestad GA.Berova N. Bioorg. Med. Chem. 2008, 16: 6544Reference Ris Wihthout Link - 11b
Balaz M.Bitsch-Jensen K.Mammana A.Ellestad GA.Nakanishi K.Berova N. Pure Appl. Chem. 2007, 79: 801Reference Ris Wihthout Link - 11c
Balaz M.Li BC.Steinkruger JD.Ellestad GA.Nakanishi K.Berova N. Org. Biomol. Chem. 2006, 4: 1865Reference Ris Wihthout Link - 11d
Balaz M.De Napoli M.Holmes AE.Mammana A.Nakanishi K.Berova N.Purrello R. Angew. Chem. Int. Ed. 2005, 44: 4006Reference Ris Wihthout Link - 12
Sitaula S.Reed SM. Bioorg. Med. Chem. Lett. 2008, 18: 850 - 13a
Murashima T.Hayata K.Saiki Y.Matsui J.Miyoshi D.Yamada T.Miyazawa T.Sugimoto N. Tetrahedron Lett. 2007, 48: 8514Reference Ris Wihthout Link - 13b
Morales-Rojas H.Kool ET. Org. Lett. 2002, 4: 4377Reference Ris Wihthout Link - 14a
Endo M.Fujitsuka M.Majima T. J. Org. Chem. 2008, 73: 1106Reference Ris Wihthout Link - 14b
Endo M.Shiroyama T.Fujitsuka M.Majima T. J. Org. Chem. 2005, 70: 7468Reference Ris Wihthout Link - 14c
Endo M.Seeman NC.Majima T. Angew. Chem. Int. Ed. 2005, 44: 6074Reference Ris Wihthout Link - 15
Mel’nikov SM.Khan MO.Lindman B.Jonsson B.
J. Am. Chem. Soc. 1999, 121: 1130 - 16
Sen A.Nielsen PE. Nucleic Acids Res. 2007, 35: 3367 - 17
Reddy MR.Shibata N.Kondo Y.Nakamura S.Toru T. Angew. Chem. Int. Ed. 2006, 45: 8163 - 18a
Shakeel S.Karim S.Ali A. J. Chem. Technol. Biotechnol. 2006, 81: 892Reference Ris Wihthout Link - 18b
Eriksson M.Nielsen PE. Nat. Struct. Biol. 1996, 3: 410Reference Ris Wihthout Link - 19a
Hou XL.Xu M.Wu LX.Shen JC. Colloids Surf., B: Biointerfaces 2005, 41: 181Reference Ris Wihthout Link - 19b
Bonner G.Klibanov AM. Biotechnol. Bioeng. 2000, 68: 339Reference Ris Wihthout Link - 20
Mohamadi F.Richards NGJ.Guida WC.Liskamp R.Lipton M.Caufield C.Chang G.Hendrickson T.Still WC. J. Comput. Chem. 1990, 11: 440