Synthesis and self-assembly of Boc-protected bisguanidines
Received date: 2016-03-25
Online published: 2018-03-05
邹晓亮, 顾君, 孙雨人, 钱群 . Boc保护的二胍基化合物的合成及自组装[J]. 上海大学学报(自然科学版), 2018 , 24(1) : 66 -73 . DOI: 10.12066/j.issn.1007-2861.1768
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.
| [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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