Tailor-made naphthyridines: Self-assembling multiple hydrogen-bonded supramolecular architectures from dimer to helix

2007 ◽  
Vol 846 (1-3) ◽  
pp. 97-107 ◽  
Author(s):  
Shyamaprosad Goswami ◽  
Swapan Dey ◽  
John F. Gallagher ◽  
Alan J. Lough ◽  
Santiago García-Granda ◽  
...  
Keyword(s):  
Supramolecular Architectures ◽  
Self Assembling ◽  
Hydrogen Bonded

New supramolecular architectures using hydrogen bonding

1993 ◽  
Vol 345 (1674) ◽  
pp. 49-56 ◽  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Hydrogen Bond Donor ◽  
Binding Strength ◽  
Supramolecular Architectures ◽  
Self Assembling ◽  
Donor And Acceptor ◽  
The Stability ◽  
Bonded Complexes ◽  
Hydrogen Bonded

Several new multiply hydrogen bonded complexes have been studied to determine their strength and the specificity with which they form. While many factors contribute to the stability of multiply hydrogen bonded complexes, it appears that the arrangement of the hydrogen bond donor and acceptor groups is a particularly good predictor of binding strength. The results are consistent with W. L. Jorgensen’s secondary electrostatic hypothesis. The heterocyclic recognition units that have been synthesized may serve as the basis for constructing new synthetic hosts or new self-assembling systems.

Supramolecular architectures in cytosinium 6-chloronicotinate monohydrate and 5-bromo-6-methylisocytosinium hydrogen sulfate

2018 ◽  
Vol 74 (3) ◽  
pp. 325-331
Author(s):  
Robert Swinton Darious ◽  
Nithianantham Jeeva Jasmine ◽  
Ammasai Karthikeyan ◽  
Packianathan Thomas Muthiah ◽  
Franc Perdih
Keyword(s):  
Hydrogen Bonds ◽  
Pyrimidine Ring ◽  
Hydrogen Sulfate ◽  
X Ray Diffraction ◽  
Sulfate Ion ◽  
Sulfate Ions ◽  
Supramolecular Architectures ◽  
Hydrated Salt ◽  
Sheet Structure ◽  
Hydrogen Bonded

Aminopyrimidine derivatives are biologically important as they are components of nucleic acids and drugs. The crystals of two new salts, namely cytosinium 6-chloronicotinate monohydrate, C4H6N3O+·C6H3ClNO2−·H2O, (I), and 5-bromo-6-methylisocytosinium hydrogen sulfate (or 2-amino-5-bromo-4-oxo-6-methylpyrimidinium hydrogen sulfate), C5H7BrN3O+·HSO4−, (II), have been prepared and characterized by single-crystal X-ray diffraction. The pyrimidine ring of both compounds is protonated at the imine N atom. In hydrated salt (I), the primaryR22(8) ring motif (supramolecular heterosynthon) is formedviaa pair of N—H...O(carboxylate) hydrogen bonds. The cations, anions and water molecule are hydrogen bonded through N—H...O, N—H...N, O—H...O and C—H...O hydrogen bonds, formingR22(8),R32(7) andR55(21) motifs, leading to a hydrogen-bonded supramolecular sheet structure. The supramolecular double sheet structure is formedviawater–carboxylate O—H...O hydrogen bonds and π–π interactions between the anions and the cations. In salt (II), the hydrogen sulfate ions are linkedviaO—H...O hydrogen bonds to generate zigzag chains. The aminopyrimidinium cations are embedded between these zigzag chains. Each hydrogen sulfate ion bridges two cationsviapairs of N—H...O hydrogen bonds andvice versa, generating twoR22(8) ring motifs (supramolecular heterosynthon). The cations also interact with one anotherviahalogen–halogen (Br...Br) and halogen–oxygen (Br...O) interactions.

scholarly journals Dual self-assembly of supramolecular peptide nanotubes to provide stabilisation in water

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Julia Y. Rho ◽  
Henry Cox ◽  
Edward D. H. Mansfield ◽  
Sean H. Ellacott ◽  
Raoul Peltier ◽  
...  
Keyword(s):  
Self Assembly ◽  
Supramolecular Assembly ◽  
Ordered Structures ◽  
Peptide Bonds ◽  
Self Assembling ◽  
Peptide Hydrogen ◽  
Aqueous Conditions ◽  
Β Sheet ◽  
Peptide Core ◽  
Hydrogen Bonded

Abstract Self-assembling peptides have the ability to spontaneously aggregate into large ordered structures. The reversibility of the peptide hydrogen bonded supramolecular assembly make them tunable to a host of different applications, although it leaves them highly dynamic and prone to disassembly at the low concentration needed for biological applications. Here we demonstrate that a secondary hydrophobic interaction, near the peptide core, can stabilise the highly dynamic peptide bonds, without losing the vital solubility of the systems in aqueous conditions. This hierarchical self-assembly process can be used to stabilise a range of different β-sheet hydrogen bonded architectures.

Novel Hydrogen-bonded Three-dimensional Supramolecular Architectures Containing 2D Honeycomb Networks or 2D Grids

2006 ◽  
Vol 24 (10) ◽  
pp. 1352-1358 ◽  
Author(s):  
Dong-Sheng Li ◽  
Cai-Hua Zhou ◽  
Yao-Yu Wang ◽  
Feng Fu ◽  
Ya-Pan Wu ◽  
...  
Keyword(s):  
Three Dimensional ◽  
Supramolecular Architectures ◽  
Hydrogen Bonded

Designer cyclopeptides for self-assembled tubular structures

2000 ◽  
Vol 72 (3) ◽  
pp. 365-372 ◽  
Author(s):  
Darshan Ranganathan ◽  
C. Lakshmi ◽  
V. Haridas ◽  
M. Gopikumar
Keyword(s):  
Design Strategy ◽  
Single Step ◽  
Simple Design ◽  
Tubular Structures ◽  
Peptide Nanotubes ◽  
X Ray ◽  
X Ray Crystallography ◽  
Self Assembling ◽  
Direct Condensation ◽  
Hydrogen Bonded

A simple design strategy for a facile and direct entry into hydrogen-bonded peptide nanotubes is delineated with polymethylene-bridged cystine-based macrocycles. The key feature of the design is the placement of a pair of self-complementary hydrogen-bonding (NH–CO or NH–CO–NH) groups at almost opposite poles of the ring. A large variety of cyclobisamides and bisureas prepared in a single step by direct condensation of commercially available 1,ω-alkane dicarbonyl dichloride or diisocyanate with either cystine diOMe or its extended bispeptide were examined by X-ray crystallography and shown to possess an inherent property of self-assembling into hydrogen-bonded, open-ended, hollow tubular structures. The totally hydrophobic interior of the cyclobisamide tubes creates a micro environment capable of solubilizing highly lipophilic substances in water. The cyclic bisurea tubes are demonstrated to act as excellent receptors for selective binding to 1,ω-alkane dicarboxylates. The scope of the design is extended to the creation of tubular structures by stacking of rings through aromatic π-π interactions.

Hydrogen-bonded supramolecular architectures based on [Zr(C2O4)4]4−anion and protonated polyamine cations

CrystEngComm ◽  
2017 ◽  
Vol 19 (12) ◽  
pp. 1633-1642 ◽  
Author(s):  
Monia Hamdouni ◽  
Siwar Walha ◽  
Carine Duhayon ◽  
Ahlem Kabadou ◽  
Jean-Pascal Sutter
Keyword(s):  
Supramolecular Architectures ◽  
Hydrogen Bonded

Hydrogen bonded supramolecular architectures of organic salts based on 5,7-dimethyl-1,8-naphthyridine-2-amine and acidic compounds

2010 ◽  
Vol 975 (1-3) ◽  
pp. 128-136 ◽  
Author(s):  
Shouwen Jin ◽  
Wenbiao Zhang ◽  
Li Liu ◽  
Hongfang Gao ◽  
Daqi Wang ◽  
...  
Keyword(s):  
Organic Salts ◽  
Supramolecular Architectures ◽  
Acidic Compounds ◽  
Hydrogen Bonded
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