Ice-like encapsulated water by two cholic acid moieties

Soto, Victor H.; Álvarez, Mercedes; Meijide, Francisco; Trillo, Juan V.; Antelo, Álvaro; Jover, Aida; Galantini, Luciano; Tato, José Vázquez

doi:10.1016/j.steroids.2012.07.003

Cited by 8 publications

(17 citation statements)

References 50 publications

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“…The solution of the crystal structures of the four 3,12-dihydroxy epimers of DCA was used to successfully predict the hydrogen bond network of the 3-oxo-12α-hydroxy derivative [8]. On the other hand, the ability to form hydrogen bonds by CA plus the characteristics of head-to-head dimers have been used for designing a crystal, in which a single water molecule is encapsulated between two cholic residues in an ice-like structure [17]. Miyata et al have also studied the supramolecular chirality in crystals generated from chiral [37][38][39][40] and achiral [41,42] molecules, and rationalized a hierarchical organization in BA crystals like that in proteins [3,43,44].…”

Section: R1mentioning

confidence: 99%

A Standard Structure for Bile Acids and Derivatives

et al. 2018

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Abstract:The crystal structures of two ester compounds (a monomer in its methyl ester form, with an amino isophthalic group, and a dimer in which the two steroid units are linked by a urea bridge recrystallized from ethyl acetate/methanol) derived from cholic acid are described. Average bond lengths and bond angles from the crystal structures of 26 monomers and four dimers (some of them in several solvents) of bile acids and esters (and derivatives) are used for proposing a standard steroid nucleus. The hydrogen bond network and conformation of the lateral chain are also discussed. This standard structure was used to compare with the structures of both progesterone and cholesterol.

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Section: R1mentioning

confidence: 99%

A Standard Structure for Bile Acids and Derivatives

et al. 2018

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“…Selected signals of NMR spectra of bispirostanic steroids 8a-c and 10a-b are shown in Tables 3 and 4. It should be considered that the background information diffraction can be useful to give an idea of the structure of sup solutions [43][44][45]. The crystal structures of sapogenin dime structural issues that will be subject to the structural characteri how it links with the spacer group (tail-to-tail or head-to-head).…”

Section: Nmr Elucidationmentioning

confidence: 99%

“…The crystal structures of sapogenin dime structural issues that will be subject to the structural characteri how it links with the spacer group (tail-to-tail or head-to-head). T It should be considered that the background information of the crystal structure from X-ray diffraction can be useful to give an idea of the structure of supramolecular aggregates in aqueous solutions [43][44][45]. The crystal structures of sapogenin dimers provide information to resolve structural issues that will be subject to the structural characteristics of the steroidal framework and how it links with the spacer group (tail-to-tail or head-to-head).…”

Section: Nmr Elucidationmentioning

confidence: 99%

“…In addition to the last-referred paper, as far as we identify, only Bertolasi et al [46], Bai et al [47] Ghosh et al [48], and Dias et al [49] have registered crystal structures of a bile acid dimer, a bile acid cyclodimer, and a cyclotrimer derived from deoxycholate, respectively. It should be considered that the background information diffraction can be useful to give an idea of the structure of sup solutions [43][44][45]. The crystal structures of sapogenin dime structural issues that will be subject to the structural characteri how it links with the spacer group (tail-to-tail or head-to-head).…”

Section: Nmr Elucidationmentioning

confidence: 99%

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Mesoscale Assembly of Bisteroidal Esters from Terephthalic Acid

et al. 2020

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A new series of bisteroidal esters was synthesized using a spacer group, sterols and sapogenins as substrates. Steroidal dimers were prepared in high yields employing diesters of terephthalic acid as linkages at the 3β, 3′β steroidal positions. In all attempts to crystallize bisteroids, it was observed that the compounds tended to self-organize in solution, which was detected when employing various solvent systems. The non-covalent interactions (van der Waals) of the steroidal moieties of this series of symmetrical bisteroids, the polarity of the solvents systems, and the different solubilities of the bisteroid aggregates, indeed induce the molecules to self-assemble into supramolecular structures with well-defined organization. Our results show that the self-assembled structures for the bisteroidal derivatives depend on the solvent system used: with hexane/EtOAc, membrane-shaped structures were obtained, while pure EtOAc afforded strand-shaped arrangements. In the CHCl3/CH3OH system, thin strands were formed, since van der Waals interactions are lowered in this system, as a consequence of the increased solubility of the bisteroids in CHCl3. Based on the characterization by SEM and XRD, we show evidence that the phenomenon of self-assembly of bisteroids occurs presenting different morphologies depending on the solvent used. The new steroidal dimer derivatives were characterized by NMR, TGA, DSC, SEM, and XRD. Finally, the molecular structure of one bisteroid was confirmed by single-crystal X-ray analysis.

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“…30 The ability of forming hydrogen bonds by cholic acid and the characteristics of head-to-head dimers has been used for designing a crystal in which a single water molecule is encapsulated between two cholic residues in an ice-like structure. 31 All this information suggests that interesting properties could arise from a dimer compound in which the characteristics of urea and cholic acid were put together in a single molecule. Thus we have selected a simple urea bridge which provides planarity and a shorter distance between the steroids, which a priori will restrict the spatial orientation of the steroid nucleus.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure of a Head-to-Head Bis(cholic)-Urea Dimer

Meijide

Trillo

Frutos

et al. 2014

Proceedings of the 18th International Electronic Conference on Synthetic Organic Chemistry

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A head-to-head dimer of cholic acid linked at C3 carbon atoms by a urea bridge was synthesized and the crystal structure was studied. The crystal belongs to the monoclinic crystal system, space group I 2 . The packing shows a bilayer structure with alternating hydrophobic and hydrophilic layers. The horizontal and vertical planes of the two cholic residues are almost parallel to each other, the vertical ones being perpendicular to the bilayers. The hydrogen bond network is two-dimensional as it does not propagate in the direction perpendicular to the bilayers. It is noteworthy that the nitrogen atoms of the urea bridge do not participate in that network. The carbonyl urea group and only one of the ester of the two side chains form hydrogen bonds with two other dimers through the steroid hydroxy O7-H and O12-H groups. This means that each dimer forms eight hydrogen bonds but only four are different.

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Ice-like encapsulated water by two cholic acid moieties

Cited by 8 publications

References 50 publications

A Standard Structure for Bile Acids and Derivatives

A Standard Structure for Bile Acids and Derivatives

Mesoscale Assembly of Bisteroidal Esters from Terephthalic Acid

Crystal Structure of a Head-to-Head Bis(cholic)-Urea Dimer

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