Novel Nucleobase-Decorated Tripodands: Synthesis and Supramolecular Properties

Mirabela Ligia Golban; Vlad Paşcanu; Niculina D. Hădade; Lidia Pop; Crina Socaci; Ion Grosu

doi:10.1055/s-0033-1340833

Synthesis, Table of Contents

Synthesis 2014; 46(09): 1229-1235
DOI: 10.1055/s-0033-1340833

paper

Novel Nucleobase-Decorated Tripodands: Synthesis and Supramolecular Properties

Mirabela Ligia Golban

^aBabeş-Bolyai University, Supramolecular Organic and Organometallic Chemistry Center (SOOMCC), Cluj-Napoca, 11 Arany Janos str., 400028, Cluj-Napoca, Romania

,

Vlad Paşcanu

^aBabeş-Bolyai University, Supramolecular Organic and Organometallic Chemistry Center (SOOMCC), Cluj-Napoca, 11 Arany Janos str., 400028, Cluj-Napoca, Romania

,

Niculina D. Hădade

^aBabeş-Bolyai University, Supramolecular Organic and Organometallic Chemistry Center (SOOMCC), Cluj-Napoca, 11 Arany Janos str., 400028, Cluj-Napoca, Romania

,

Lidia Pop

^aBabeş-Bolyai University, Supramolecular Organic and Organometallic Chemistry Center (SOOMCC), Cluj-Napoca, 11 Arany Janos str., 400028, Cluj-Napoca, Romania

,

Crina Socaci*

^aBabeş-Bolyai University, Supramolecular Organic and Organometallic Chemistry Center (SOOMCC), Cluj-Napoca, 11 Arany Janos str., 400028, Cluj-Napoca, Romania

^bNational Institute of Research and Development for Isotopic and Molecular Technologies (INCDTIM), Cluj-Napoca, 65-103 Donath str., 400293, Cluj-Napoca, Romania Fax: +40(264)590818 Email: igrosu@chem.ubbcluj.ro Email: crina.socaci@itim-cj.ro

,

Ion Grosu*

^aBabeş-Bolyai University, Supramolecular Organic and Organometallic Chemistry Center (SOOMCC), Cluj-Napoca, 11 Arany Janos str., 400028, Cluj-Napoca, Romania

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Abstract

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Abstract

We describe herein the synthesis and characterization of new rigid nucleobase-decorated tripodands. The synthetic strategy involves the use of new azide functionalized nucleobases (adenine, thymine, and uracil). ES(+)-MS studies of hydrogen-bonding self-association as well as associations with complementary nucleosides are also reported.

Key words

azide-functionalized nucleobases - tripodands - click chemistry - H-bonding

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References

References

1a Koonin EV. Nucleic Acids Res. 2009; 37: 1011
1b Attwater J, Holliger P. Nature (London) 2012; 491: 48
1c Vaidya N, Manapat ML, Chen IA, Xulvi-Brunet R, Hayden EJ, Lehman N. Nature (London) 2012; 491: 72
1d Lilley DM. J, Sutherland J. Philos. Trans. R. Soc., B 2011; 366: 2853

2a Yoshimi Y, Watanabe S, Shinomiya T, Makino A, Toyoda M, Ikekita M. Brain Res. 2003; 991: 113
2b Damaraju D, Damaraju VL, Brun M, Mowles D, Kuzma M, Berendt RC, Sawyer MB, Cass CE. Biochem. Pharmacol. 2008; 75: 1901
2c Novak I, Kovać B. Spectrochim. Acta, Part A 2005; 61: 2771
2d Ruiz J, Lorenzo J, Sanglas L, Cutillas N, Vicente C, Villa MD, Avilés FX, López G, Moreno V, Pérez J, Bautista D. Inorg. Chem. 2006; 45: 6347

3a Beobide G, Castillo O, Cepeda J, Luque A, Perez-Yãnez S, Roman P, Thomas-Gipson J. Coord. Chem. Rev. 2013; 257: 2716
3b Li X, Kuang Y, Xu B. Soft Matter 2012; 8: 2801
3c Arnal-Hérault C, Barboiu M, Pasc A, Michau M, Perriat P, van der Lee A. Chem. Eur. J. 2007; 13: 6792

4a Li X.-Q, Jia M.-X, Wang X.-Z, Jiang X.-K, Li Z.-T, Chen G.-J, Yu Y.-H. Tetrahedron 2005; 61: 9600
4b Sessler JL, Jayawickramarajah J. Chem. Commun. 2005; 1939
4c Sessler JL, Lawrence CM, Jayawickramarajah J. Chem. Soc. Rev. 2007; 36: 314
4d Chattopadhyay P, Pandey PS. Tetrahedron Lett. 2008; 49: 4640

5a Cheng S, Zhang M, Dixit N, Moore RB, Long TE. Macromolecules 2012; 45: 805
5b Hemp ST, Long TE. Macromol. Biosci. 2012; 12: 29
5c McHale R, O’Reilly RK. Macromolecules 2012; 45: 7665

6a Verma S, Mishra AK, Kumar J. Acc. Chem. Res. 2010; 43: 79
6b An J, Geib SJ, Rosi NL. J. Am. Chem. Soc. 2010; 132: 38
6c Xu W, Wang J, Jacobsen MF, Mura M, Yu M, Kelly RE. A, Meng Q, Lægsgaard E, Stensgaard I, Linderoth TR, Kjems J, Kantorovich LN, Gothelf KV, Besenbacher F. Angew. Chem. Int. Ed. 2010; 49: 9373
6d Pérez-Yáñez S, Beobide G, Castillo O, Cepeda J, Luque A, Román P. Cryst. Growth Des. 2013; 13: 3057

7a Plietzsch O, Schiling CI, Tolev M, Nieger M, Richert C, Muller T, Braese S. Org. Biomol. Chem. 2009; 7: 4734
7b Singh A, Tolev M, Schiling CI, Braese S, Griesser H, Richert C. J. Org. Chem. 2012; 77: 2718

8 Trakossas S, Argyropoulou EC, Hadjipavlou-Litina DJ. Tetrahedron Lett. 2011; 52: 1673
9 Roy S, Bag SS, Basak A. Tetrahedron 2012; 68: 8600
10 Wei B, Hui Q, Sherman JC. Chem. Commun. 2012; 48: 109
11 Davis AP, Wareham RS. Angew. Chem. Int. Ed. 1999; 38: 2978
12 Perraud O, Lefevre S, Robert V, Martinez A, Dutasta J.-P. Org. Biomol. Chem. 2012; 10: 1056
13 Schmitt A, Chatelet B, Collin S, Dutasta J.-P, Martinez A. Chirality 2013; 25: 475
14 Perraud O, Robert V, Martinez A, Dutasta J.-P. Chem. Eur. J. 2011; 17: 4177
15 Soberats B, Martínez L, Sanna E, Sampedro A, Rotger C, Costa A. Chem. Eur. J. 2012; 18: 7533
16 Piron F, Oprea C, Cismas C, Terec A, Roncali J, Grosu I. Synthesis 2010; 1639

See for example:

17a Xiwg Y, Hixson SS, Zimmermann RA. Tetrahedron Lett. 1990; 31: 5649
17b Polshakov D, Rai S, Wilson RM, Mack ET, Vogel M, Krause JA, Burdzinski G, Platz MS. Biochemistry 2005; 44: 11241
17c Chirio M.-C, Brethes D, Napias C, Grandier-Vazeille X, Rakotomanana F, Chevallier J. Eur. J. Biochem. 1990; 194: 293

See for example:

18a Zhang Q, Hua G, Bhattacharyya P, Slawin AM. Z, Woollins JD. Dalton Trans. 2003; 3250
18b Nguyen C, Ruda GF, Schipani A, Kasinathan G, Leal I, Musso-Buendia A, Kaiser M, Brun R, Ruiz-Pérez LM, Sahlberg B.-L, Johansson NG, González-Pacanowska D, Gilbert IH. J. Med. Chem. 2006; 49: 4183
18c Zhang Q, Hua G, Bhattacharyya P, Slawin AM. Z, Woollins JD. Eur. J. Inorg. Chem. 2003; 2426
18d Roy B, Dutta S, Chowdhary A, Basak A, Dasgupta S. Bioorg. Med. Chem. Lett. 2008; 18: 5411

19 Fedorov AY, Shchepalov AA, Bolshakov AV, Shavyrin AS, Kurskii YA, Finet JP, Zelentsov SV. Russ. Chem. Bull. 2004; 53: 370
20 Shendage DM, Froehlich R, Haufe G. Org. Lett. 2004; 6: 3675
21 Ferrer E, Alibés R, Busqué F, Figueredo M, Font J, March P. J. Org. Chem. 2009; 74: 2425
22 Michel BY, Strazewski P. Tetrahedron 2007; 63: 9836
23 Zhou J, Shevlin PB. Synth. Commun. 2010; 27: 3591

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