Crystal and molecular structures of the inclusion compounds of cholic acid with methanol, ethanol and 1-propanol

Jones, Eleanor Lloyd; Nassimbeni, Luigi R.

doi:10.1107/s0108768189014205

Cited by 46 publications

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“…Recrystallization of CA from fifty or more alcohols results in the formation of only eight inclusion crystals. Moreover, only two alcohols are included in a bilayer structure,16c while another five smaller alcohols are found in a crossing structure 20–22. Table 4 shows the lattice parameters of the inclusion crystals and the host framework types.…”

Section: Resultsmentioning

confidence: 99%

The Effect of a Host–Guest Hydrogen Bond on the Inclusion of Alcoholic Guests in the Host Cavities of Cholamide

et al. 2005

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Fifty eight inclusion crystals of cholamide (CAM) with aliphatic alcohols have been systematically investigated by X‐ray crystallography. The host frameworks of the inclusion crystals can be categorized into three structural types: bilayer, herringbone, and crossing structures. Most of the guests are included in bilayer structures, which can be further divided into four sub‐types. The host frameworks isomerize depending on the size and shape of the guest molecules. This dependence is clearly evaluated by the relationship between the volume of the guest molecules and the packing coefficient of the void space in the host frameworks. Although the host frameworks with the cavities and the structural isomerization are very similar to those of the inclusion crystals of cholic acid (CA), the inclusion behavior of aliphatic alcohols in the two hosts is completely different: fifty four alcohols can be included in the bilayer‐type structures of CAM, but only two in those of CA. This is attributed to their different functional groups, which lead to different hydrogen‐bond networks with the guest alcohols. The result in the two hosts is a good example to understand the effect of host–guest hydrogen bonds on guest inclusion in cavities that are identical in size and shape. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Resultsmentioning

confidence: 99%

The Effect of a Host–Guest Hydrogen Bond on the Inclusion of Alcoholic Guests in the Host Cavities of Cholamide

et al. 2005

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“…Their solvent capacity toward sterols and metabolic fats depends on the structure of the aggregates they form. Solid BS also form inclusion compounds with alkanols, fatty acids, polyenes, retinoids and other species [23,24]. Bile salts interact with a wide variety of compounds in solution and in real matrices (see Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Supra-molecular Association and Polymorphic Behaviour In Systems Containing Bile Acid Salts

2007

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A wide number of supra-molecular association modes are observed in mixtures containing water and bile salts, BS, (with, eventually, other components). Molecular or micellar solutions transform into hydrated solids, fibres, lyotropic liquid crystals and/or gels by raising the concentration, the temperature, adding electrolytes, surfactants, lipids and proteins. Amorphous or ordered phases may be formed accordingly. The forces responsible for this very rich polymorphism presumably arise from the unusual combination of electrostatic, hydrophobic and hydrogen-bond contributions to the system stability, with subsequent control of the supra-molecular organisation modes. The stabilising effect due to hydrogen bonds does not occur in almost all surfactants or lipids and is peculiar to bile acids and salts. Some supra-molecular organisation modes, supposed to be related to malfunctions and dis-metabolic diseases in vivo, are briefly reported and discussed.

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“…The X-ray resolved structure of cholic acid contained in the Cambridge Structural Database (CSD) 23 was chosen as a starting point in the construction process (CSD code: CHOLET01). 24 2-Naphthylcarbamate and 3,5-dinitrophenylcarbamate groups were attached to the hydroxyl groups in order to obtain the four compounds under investigation, and their starting structures were energy minimized.…”

Section: Resultsmentioning

confidence: 99%

Cholic Acid Derivatives Containing Both 2-Naphthylcarbamate and 3,5-Dinitrophenylcarbamate Groups: A Combined Circular Dichroism−Molecular Mechanics Approach to the Definition of Their Molecular Conformation

et al. 2003

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CD spectra of the chiral auxiliaries for enantioselective HPLC N-allyl-N'-methyl-3,12-bis(2-naphthyl)carbamoyloxy-7-(3,5-dinitrophenyl)carbamoyloxycholan-24-amide (1), N-allyl-N'-methyl-3-(3,5-dinitrophenyl)carbamoyloxy-7,12-bis(2-naphthyl)carbamoyloxycholan-24-amide (2), N-allyl-N'-methyl-3,7-bis(2-naphthyl)carbamoyloxy-12-(3,5-dinitrophenyl)carbamoyloxycholan-24-amide (3), and N-allyl-N'-methyl-3,7,12-tris(2-naphthyl)carbamoyloxycholan-24-amide (4) are presented. To determine the preferred conformations of those chiral auxiliaries, a random search based on the aromatic side-chain conformational degrees of freedom was performed and the energy was minimized using two different molecular mechanics force fields. The low energy structures presenting common features were arranged in groups and selected exploiting appropriate filters. The calculation of theoretical CD spectra according to the De Voe model has allowed a further discrimination among the conformations, specifying which of them gave calculated CD spectra in acceptable agreement with the experimental ones. Finally, taking into account the additivity of the contributions of each 2-naphthylcarbamate chromophore to the CD spectrum of the cholic acid derivatives, and, hence, choosing, for derivatives 1-3, those conformations in which the 2-naphthylcarbamate groups take a similar disposition as in 4, the preferentially assumed conformation of each compound was obtained. A molecular dynamics simulation in the presence of acetonitrile allowed the fluctuations of one of the structures, used as a test case, depending on environmental effects, to be examined.

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Crystal and molecular structures of the inclusion compounds of cholic acid with methanol, ethanol and 1-propanol

Cited by 46 publications

References 0 publications

The Effect of a Host–Guest Hydrogen Bond on the Inclusion of Alcoholic Guests in the Host Cavities of Cholamide

The Effect of a Host–Guest Hydrogen Bond on the Inclusion of Alcoholic Guests in the Host Cavities of Cholamide

Supra-molecular Association and Polymorphic Behaviour In Systems Containing Bile Acid Salts

Cholic Acid Derivatives Containing Both 2-Naphthylcarbamate and 3,5-Dinitrophenylcarbamate Groups: A Combined Circular Dichroism−Molecular Mechanics Approach to the Definition of Their Molecular Conformation

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