Research Articles

Synthesis and self-assembly of Boc-protected bisguanidines

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  • College of Sciences, Shanghai University, Shanghai 200444, China

Received date: 2016-03-25

  Online published: 2018-03-05

Abstract

Guanidinium cations are widely used to recognize sulfate and phosphate anions. However, there are few reports about neutral guanidines. In this work, several Boc-protected guanidines are synthesized. With nuclear magnetic resonance (NMR) dilution experiments and single crystal X-ray diffraction. It has been found that there are intermolecular interaction among neutral bisguanidinium in solution and solid state as well.

Cite this article

ZOU Xiaoliang, GU Jun, SUN Yuren, QIAN Qun . Synthesis and self-assembly of Boc-protected bisguanidines[J]. Journal of Shanghai University, 2018 , 24(1) : 66 -73 . DOI: 10.12066/j.issn.1007-2861.1768

References

[1] Schmuck C, Geiger L . Carboxylate binding by guanidiniocarbonyl pyrroles: from self-assembly to peptide receptors[J]. Cur Org Chem, 2003,7(14):1485-1502.
[2] Schmuck C . How to improve guanidinium cations for oxoanion binding in aqueous solution: the design of artificial peptide receptors coordination[J]. Coor Chem Rev, 2006,250(23):3053-3067.
[3] Pia$\acute{u}$tek A M, Gray M, Anslyn E V . Guanidinium groups act as general-acid catalysts in phosphoryl transfer reactions: a two-proton inventory on a model system[J]. J Am Chem Soc, 2004,126(32):9878-9879.
[4] Schmuck C, Wienand W . Highly stable self-assembly in water: ion pair driven dimerization of a guanidiniocarbonyl pyrrole carboxylate zwitterion[J]. J Am Chem Soc, 2003,125(2):452-459.
[5] Schmuck C, Rehm T, Geiger L , et al. Synjournal and self-association properties of flexible guanidiniocarbonyl pyrrole-carboxylate zwitterions in DMSO: intra- versus intermolecular ion pairing[J]. J Org Chem, 2007,72(16):6162-6170.
[6] Schmuck C, Lex J . Acetate binding within a supramolecular network formed by a guanidiniocarbonyl pyrrole cation in the solid state[J]. Org Lett, 1999,1(11):1779-1781.
[7] Dixon R P, Geib S J , HamiltonA D. Molecular recognition: bis-acylguanidiniums provide a simple family of receptors for phosphodiesters[J]. J Am Chem Soc, 1992,114(1):365-366.
[8] GrosselM C, MerckelaD A S, HutchingsM G . The effect of preorganisation on the solid state behaviour of simple `aromatic-cored' bis(guanidinium) sulfates[J]. Cryst Eng Comm, 2003,5(16):77-81.
[9] Ando N, Terashima S . A novel synjournal of the 2-amino-1H-imidazol 4-carbaldehyde derivatives and its application to the efficient synjournal of 2-aminoimidazole alkaloids, oroidin, hymenidin, dispacamide, monobromodispacamide, and ageladine A[J]. Tetrahedron, 2010,66(32):6224-6237.
[10] Park J H, Ko K C, Son S U . Photocatalysis by phenothiazine dyes: visible-light-driven oxidative coupling of primary amines at ambient temperature[J]. Org Lett, 2012,14(21):5502-5505.
[11] Courchay F C, Sworen J C, Ghiviriga I , et al. Understanding structural isomerization during ruthenium-catalyzed olefin metajournal: a deuterium labeling study[J]. Organometallics, 2006,25(26):6074-6086.
[12] Huber J D, Bentzien J, BoyerS J, et al. Identification of a potent sodium hydrogen exchanger isoform 1(NHE1) inhibitor with a suitable profile for chronic dosing and demonstrated cardioprotective effects in a preclinical model of myocardial infarction in the rat[J]. J Med Chem, 2012,55(16):7114-7140.
[13] Schmuck C . Self-assembly of 2-(guanidiniocarbonyl)-pyrrole-4-carboxylate in dimethyl sulfoxide: an entropy driven oligomerization[J]. Tetrahedron, 2001,57(15):3063-3067.
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