Enantioselective inclusion of (R)-phenylglycyl-(R)-phenylglycine with benzyl methyl sulfoxides

Akazome, Motohiro; Hirabayashi, Atsushi; Ogura, Katsuyuki

doi:10.1016/j.tet.2004.10.032

Cited by 13 publications

(4 citation statements)

References 50 publications

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“…Supramolecular structures based on lower peptides may be subdivided into two groups: peptide nanotubes and peptide clathrates. Peptide nanotubes, known from the pioneering studies of Ghadiri and co-workers, have attracted a significant research effort. − Peptide clathrates are crystalline materials comprising guest components in a peptide matrix. − The crystalline dipeptides studied in this work represent a somewhat intermediate position exhibiting peptide nanotubes organized inside a crystal matrix.…”

Section: Resultsmentioning

confidence: 99%

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Micropores in Crystalline Dipeptides as Seen from the Crystal Structure, He Pycnometry, and¹²⁹Xe NMR Spectroscopy

et al. 2006

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Eight crystalline dipeptides were studied: AV (Ala-Val), VA (Val-Ala), AI (Ala-Ile), VV (Val-Val), IA (Ile-Ala), IV (Ile-Val), VI (Val-Ile), and LS (Leu-Ser) (all LL isomers). The first seven form an isostructural series (space group P6(1)), whereas LS has a different structure (P6(5)). All structures display H-bonded tubular assemblies of the dipeptide molecules resulting in open ultramicropores in the form of isolated one-dimensional (1D) channels. The total porosity of the materials ranges from 4 to 12% (micropore volume from 0.04 to 0.12 cm(3)/g). Calculations based on the crystal structures, He pycnometry, and solid-state (129)Xe NMR methods were used to obtain a comprehensive description of the geometry and properties of the micropores. The following order was established for the channel diameter: AV > VA > AI > VV > IA > IV > VI, with >5 A for AV and <4 A for VI; LS is close to AI. The observed sorption behavior cannot be described adequately based on the crystal structure and can only be understood if one takes into account the dynamics of the host matrix. The pores are chiral, with the center of the channel describing a right-handed helix (left-handed for LS). The following order was established for the channel helicity: VA > IA > IV > AV approximately AI approximately VV > VI > LS, with a helix diameter of approximately 2 A for VA, IA, and IV and approximately 1 A or less for the remaining dipeptides. A comparison of the dipeptides studied with other supramolecular materials is given and the potential for applications is discussed.

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Section: Resultsmentioning

confidence: 99%

“…[90][91][92][93][94] Peptide clathrates are crystalline materials comprising guest components in a peptide matrix. [95][96][97][98][99][100][101] The crystalline dipeptides studied in this work represent a somewhat intermediate position exhibiting peptide nanotubes organized inside a crystal matrix.…”

Section: Resultsmentioning

confidence: 99%

Micropores in Crystalline Dipeptides as Seen from the Crystal Structure, He Pycnometry, and¹²⁹Xe NMR Spectroscopy

et al. 2006

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“…Inclusion compounds of several other dipeptides reveal a similar layered organization with guest molecules included in the interlayer space. As demonstrated in a series of inclusions with leucyl-alanine 28 and various arylglycyl-arylglycines, [34][35][36][37][38] these crystals may have both parallel or anti-parallel arrangements of molecules in the b-sheet but both sides of the b-sheet layer, as in the LL inclusions, are equivalent and the guest molecules are attached (H-bonds) to the layer from both sides.…”

Section: Crystal Structuresmentioning

confidence: 99%

The ability of lower peptides to form co-crystals: inclusion compounds of Leu-Leu-Leu tripeptide with pyridine and picolines

et al. 2007

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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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Enantioselective inclusion of (R)-phenylglycyl-(R)-phenylglycine with benzyl methyl sulfoxides

Cited by 13 publications

References 50 publications

Micropores in Crystalline Dipeptides as Seen from the Crystal Structure, He Pycnometry, and¹²⁹Xe NMR Spectroscopy

Micropores in Crystalline Dipeptides as Seen from the Crystal Structure, He Pycnometry, and¹²⁹Xe NMR Spectroscopy

The ability of lower peptides to form co-crystals: inclusion compounds of Leu-Leu-Leu tripeptide with pyridine and picolines

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

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Enantioselective inclusion of (R)-phenylglycyl-(R)-phenylglycine with benzyl methyl sulfoxides

Cited by 13 publications

References 50 publications

Micropores in Crystalline Dipeptides as Seen from the Crystal Structure, He Pycnometry, and129Xe NMR Spectroscopy

Micropores in Crystalline Dipeptides as Seen from the Crystal Structure, He Pycnometry, and129Xe NMR Spectroscopy

The ability of lower peptides to form co-crystals: inclusion compounds of Leu-Leu-Leu tripeptide with pyridine and picolines

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

Contact Info

Product

Resources

About

Micropores in Crystalline Dipeptides as Seen from the Crystal Structure, He Pycnometry, and¹²⁹Xe NMR Spectroscopy

Micropores in Crystalline Dipeptides as Seen from the Crystal Structure, He Pycnometry, and¹²⁹Xe NMR Spectroscopy