X-ray studies on crystalline complexes involving amino acids and peptides. XXI. Structure of a (1:1) complex between L-phenylalanine and D-valine

Prasad, G.; Vijayan, M.

doi:10.1107/s0108270191006327

Cited by 14 publications

(5 citation statements)

References 9 publications

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“…However, such an interaction was considerably suppressed with amino acids of much lower interlayer separation, Gly (∼5 Å) and Ala (∼6 Å) (Scheme ). This result is also consistent with the attempted co-crystallization of several hydrophobic amino acids and their derivatives with mixed chirality. , Although no complex of two amino acids with the same chirality has been described, the observation of poor quality co-crystals for l -Phe: d -Ala and l -Ile: d -Ala is highly consistent with our theory. Also, the crystal quality was found to significantly improve when d -Ala was replaced by amino acids with larger side-chains strongly amenable to layer matching guided interaction.…”

Section: Resultssupporting

confidence: 90%

Deciphering the Rules for Amino Acid Co-Assembly Based on Interlayer Distances

et al. 2019

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Metabolite materials are extremely useful to obtain functional bioinspired assemblies with unique physical properties for various applications in the fields of material science, engineering, and medicine by selfassembly of the simplest biological building blocks. Supramolecular co-assembly has recently emerged as a promising extended approach to further expand the conformational space of metabolite assemblies in terms of structural and functional complexity. Yet, the design of synergistically co-assembled amino acids to produce tailormade functional architectures is still challenging. Herein, we propose a design rule to predict the supramolecular coassembly of naturally occurring amino acids based on their interlayer separation distances observed in single crystals. Using diverse experimental techniques, we demonstrate that amino acids with comparable interlayer separation strongly interact and co-assemble to produce structural composites distinctly different from their individual properties. However, such an interaction is hampered in a mixture of differentially layer-separated amino acids, which self-sort to generate individual characteristic structures. This study provides a different paradigm for the modular design of supramolecular assemblies based on amino acids with predictable properties.

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Section: Resultssupporting

confidence: 90%

Deciphering the Rules for Amino Acid Co-Assembly Based on Interlayer Distances

et al. 2019

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“…Our previous investigations included Ala, 2-aminobutyric acid (Abu), norvaline (Nva), norleucine (Nle) and Met with linear side chains, as well as Val, Ile, allo-isoleucine (aIle) and Leu with branched side chains, but not Phe. The only known structure of a 1:1 amino acid complex with this aromatic amino acid is l-Phe:d-Val (Prasad & Vijayan, 1991), which, in accordance with the observations of Dalhus (2000), forms a class II structure. Apart from this, the structure-directing properties of Phe in such complexes are unknown.…”

Section: Commentsupporting

confidence: 80%

Molecular aggregation in selected crystalline 1:1 complexes of hydrophobicD- andL-amino acids. IV. TheL-phenylalanine series

Görbitz¹,

Rissanen²,

Valkonen³

et al. 2009

Acta Crystallogr C

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The amino acid L-phenylalanine has been cocrystallized with D-2-aminobutyric acid, C(9)H(11)NO(2).C(4)H(9)NO(2), D-norvaline, C(9)H(11)NO(2).C(5)H(11)NO(2), and D-methionine, C(9)H(11)NO(2).C(5)H(11)NO(2)S, with linear side chains, as well as with D-leucine, C(9)H(11)NO(2).C(6)H(13)NO(2), D-isoleucine, C(9)H(11)NO(2).C(6)H(13)NO(2), and D-allo-isoleucine, C(9)H(11)NO(2).C(6)H(13)NO(2), with branched side chains. The structures of these 1:1 complexes fall into two classes based on the observed hydrogen-bonding pattern. From a comparison with other L:D complexes involving hydrophobic amino acids and regular racemates, it is shown that the structure-directing properties of phenylalanine closely parallel those of valine and isoleucine but not those of leucine, which shares side-chain branching at C(gamma) with phenylalanine and is normally considered to be the most closely related non-aromatic amino acid.

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“…Both amino acids are reported to crystallize as racemic compounds from racemic solutions. Interestingly, it has also been reported that S-Phe and R-Val can form a 1:1 cocrystal, while to our knowledge there have been no reports on the diastereomerically related cocrystal with the same handedness of Phe and Val. Therefore, we chose to investigate the effect of the S-Val coformer for the RS-Phe system and the S-Phe coformer for the RS-Val system.…”

Section: Resultsmentioning

confidence: 87%

Screening Approach for Identifying Cocrystal Types and Resolution Opportunities in Complex Chiral Multicomponent Systems

Groen

Kramer

et al. 2020

Crystal Growth & Design

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Co-crystallization of racemic-compound-forming chiral molecules can result in conglomerate co-crystals or diastereomerically related co-crystals, which enable the application of chiral separation techniques such as preferential crystallization and classic resolution. Here, a systematic method to identify the types and phase diagrams of co-crystals formed by chiral target compounds and candidate co-formers in a particular solvent system is presented, which allows the design of suitable chiral resolution processes. The method is based on saturation temperature measurements of specific solution compositions containing both enantiomers of chiral molecules and a co-former. This method is applied to analyze three different systems. For racemic Phenylalanine (Phe) in water/ethanol mixtures one of the enantiomers selectively co-crystallizes with the opposite enantiomer of Valine (Val), forming the more stable diastereomerically related co-crystal. The racemic compound Ibuprofen crystallizes with the non-chiral co-former 1,2-Bis(4-pyridyl)ethane (BPN) as racemic compound co-crystals. More interestingly, when combined with trans-1-(2-pyridyl)-2-(4pyridyl)-ethylene (BPE), the racemic compound Ibuprofen co-crystallizes as a conglomerate, which in principle enables the application of preferential crystallization of this racemic compound. The systematic method shows the benefit of using pseudo-binary phase diagrams. Such pseudo-binary phase diagrams depict the saturation temperature on a very specific route through the quaternary phase diagram, allowing the identification of various co-crystal types as well as the corresponding co-crystallization conditions. The systematic method can be used to identify a suitable solid phase for chiral separation and the obtained phase diagram information enables to perform a crystallization-mediated chiral resolution process design. Such a guideline for a chiral resolution process design has never been reported for conglomerate co-crystal systems such as IBU:BPE, presented in this study.

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X-ray studies on crystalline complexes involving amino acids and peptides. XXI. Structure of a (1:1) complex between L-phenylalanine and D-valine

Cited by 14 publications

References 9 publications

Deciphering the Rules for Amino Acid Co-Assembly Based on Interlayer Distances

Deciphering the Rules for Amino Acid Co-Assembly Based on Interlayer Distances

Molecular aggregation in selected crystalline 1:1 complexes of hydrophobicD- andL-amino acids. IV. TheL-phenylalanine series

Screening Approach for Identifying Cocrystal Types and Resolution Opportunities in Complex Chiral Multicomponent Systems

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