Solvent Site Preferences in the Crystal Structures of L-Leucyl-L-leucine Alcohol (1:1) Complexes.

Görbitz, Carl Henrik; Anke, Heidrun; Anke, Timm; Erkel, Gerhard; Sterner, Olov

doi:10.3891/acta.chem.scand.52-1343

Cited by 22 publications

(13 citation statements)

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“…The observed values of guest content S in Leu-Leu saturated with water, ethanol and propanols are in good agreement with single crystal XRD data for the corresponding inclusion compounds. 44,47 Also, the content of n-butanol, calculated from QCM data, corresponds to the content of isobutanol in the crystal of the dipeptide. 45 MR D values were used as size parameters for guest molecules, 19,51,54 to analyze the effect of guest size on the sorption capacity of Leu-Leu.…”

Section: Resultsmentioning

confidence: 99%

“…Firstly, hydrogen bonds are likely to form between Leu-Leu and guests such as methanol, n-butanol, chloroform, and pyridine as was similarly demonstrated for water, 47 ethanol, and propanols. 44 Secondly, a change in the packing of Leu-Leu from channel-type to layered crystals may occur upon sorption of molecules with MR D values larger than 18-20 cm 3 mol À1 (i.e. larger than propanols), as is inferred from the crystal packing of Leu-Leu with 2-methyl-1-propanol 45 and DMSO.…”

Section: Resultsmentioning

confidence: 99%

“…19 Some oligopeptide crystals obtained from solutions exhibit unusual sorption capacities. For example, the dipeptide L-leucyl-Lleucine (Leu-Leu) forms isomorphous 1 : 1 solvates with ethanol, 1-propanol, 2-propanol, 44 2-methyl-1-propanol 45 and 1 : (0.5 : 0.5) with 1-propanol : 2-propanol mixtures. 44 Transitioning from ethanol to propanols constitutes a 1.35 times increase in molecular size, according to molecular refraction (MR D ) values.…”

Section: Introductionmentioning

confidence: 99%

“…The difficulty in preparing Leu-Leu crystals with organic guests has resulted in the data reported on the interaction of Leu-Leu for only six compounds, three of which are homologues. [44][45][46][47] This information is insufficient for predicting the sorption properties of the dipeptide in ''solid Leu-Leu + vapor'' systems.…”

Section: Introductionmentioning

confidence: 99%

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Non-zeolitic properties of the dipeptide l-leucyl–l-leucine as a result of the specific nanostructure formation

Зиганшин

Safiullina

Ziganshina

et al. 2017

Phys. Chem. Chem. Phys.

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The non-zeolitic behavior of l-leucyl-l-leucine and its self-organization in solid state and from solutions with the formation of different nanostructures are reported. This dipeptide forms porous crystals, but does not exhibit molecular sieve effects typical of classical zeolites and biozeolites. The specific sorption properties of l-leucyl-l-leucine result from a change in its crystal packing from channel-type to layered-type, when binding strong proton acceptors or proton donors of molecular size greater than 18-20 cm mol. The high sorption capacity of l-leucyl-l-leucine toward dichloromethane results from the self-organization of the dipeptide, by forming nanofibers or web-like structures. The low thermal stability of clathrates of the dipeptide containing large guest molecules and the selectivity of l-leucyl-l-leucine toward alcohols over nitriles can be used to separate organic mixtures such as methanol/n-butanol and methanol/acetonitrile.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Non-zeolitic properties of the dipeptide l-leucyl–l-leucine as a result of the specific nanostructure formation

Зиганшин

Safiullina

Ziganshina

et al. 2017

Phys. Chem. Chem. Phys.

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“…When the host molecule is an optically active chiral system, the formation of inclusion compounds with racemic guests is often accompanied by enantiodiscrimination. Among the chiral molecules used for this purpose, the natural amino acids are convenient substrates for the synthesis of artificial host molecules [10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28].…”

Section: Introductionmentioning

confidence: 99%

Chiral Cocrystal Solid Solutions, Molecular Complexes, and Salts of N-Triphenylacetyl-l-Tyrosine and Diamines

Czapik

Jelecki

Kwit

2019

IJMS

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The molecular recognition process and the ability to form multicomponent supramolecular systems have been investigated for the amide of triphenylacetic acid and l-tyrosine (N-triphenylacetyl-l-tyrosine, TrCOTyr). The presence of several supramolecular synthons within the same amide molecule allows the formation of various multicomponent crystals, where TrCOTyr serves as a chiral host. Isostructural crystals of solvates with methanol and ethanol and a series of binary crystalline molecular complexes with selected organic diamines (1,5-naphthyridine, quinoxaline, 4,4′-bipyridyl, and DABCO) were obtained. The structures of the crystals were planned based on non-covalent interactions (O–H···N or N–H+···O− hydrogen bonds) present in a basic structural motif, which is a heterotrimeric building block consisting of two molecules of the host and one molecule of the guest. The complex of TrCOTyr with DABCO is an exception. The anionic dimers built off the TrCOTyr molecules form a supramolecular gutter, with trityl groups located on the edge and filled by DABCO cationic dimers. Whereas most of the racemic mixtures crystallize as racemic crystals or as conglomerates, the additional tests carried out for racemic N-triphenylacetyl-tyrosine (rac-TrCOTyr) showed that the compound crystallizes as a solid solution of enantiomers.

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Nanotube Formation by Hydrophobic Dipeptides

2001

Self Cite

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A wide range of applications has been suggested for peptide-based nanotubes, which first attracted considerable interest as model systems for membrane channels and pores. The intriguing and unprecedented observation of nanotube formation by supramolecular self-assembly of the four dipeptides L-Leu-L-Leu, L-Leu-L-Phe, L-Phe-L-Leu and L-Phe-L-Phe is described here. These simple compounds crystallize with hydrogen-bonded head-to-tail chains in the shape of helices with four to six peptide molecules per turn. The resulting structures have chiral hydrophilic channels with a van der Waals' diameter up to 10 A.

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Solvent Site Preferences in the Crystal Structures of L-Leucyl-L-leucine Alcohol (1:1) Complexes.

Cited by 22 publications

References 4 publications

Non-zeolitic properties of the dipeptide l-leucyl–l-leucine as a result of the specific nanostructure formation

Non-zeolitic properties of the dipeptide l-leucyl–l-leucine as a result of the specific nanostructure formation

Chiral Cocrystal Solid Solutions, Molecular Complexes, and Salts of N-Triphenylacetyl-l-Tyrosine and Diamines

Nanotube Formation by Hydrophobic Dipeptides

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