Molecular aggregation in selected crystalline 1:1 complexes of hydrophobic<scp>D</scp>- and<scp>L</scp>-amino acids. IV. The<scp>L</scp>-phenylalanine series

Görbitz, Carl Henrik; Rissanen, Kari; Valkonen, Arto; Husabø, Åsmund

doi:10.1107/s0108270109014309

Cited by 23 publications

(23 citation statements)

References 8 publications

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“…D-Ile and D-allo-Ileu form crystalline 1:1 complexes with D-2-aminobutyric acid (Görbitz et al 2009). This method can be used to spontaneously resolve DL-allo-Ileu into D-allo-and L-allo isomers (Dalhus and Görbitz 2000).…”

Section: Isoleucine Stereoisomers (D-ile L-allo-ile and D-allo-ile)mentioning

confidence: 98%

Nutritional and medicinal aspects of d-amino acids

2011

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This paper reviews and interprets a method for determining the nutritional value of D-amino acids, D-peptides, and amino acid derivatives using a growth assay in mice fed a synthetic all-amino acid diet. A large number of experiments were carried out in which a molar equivalent of the test compound replaced a nutritionally essential amino acid such as L-lysine (L-Lys), L-methionine (L-Met), L-phenylalanine (L-Phe), and L-tryptophan (L-Trp) as well as the semi-essential amino acids L-cysteine (L-Cys) and L-tyrosine (L-Tyr). The results show wide-ranging variations in the biological utilization of test substances. The method is generally applicable to the determination of the biological utilization and safety of any amino acid derivative as a potential nutritional source of the corresponding L-amino acid. Because the organism is forced to use the D-amino acid or amino acid derivative as the sole source of the essential or semi-essential amino acid being replaced, and because a free amino acid diet allows better control of composition, the use of all-amino-acid diets for such determinations may be preferable to protein-based diets. Also covered are brief summaries of the widely scattered literature on dietary and pharmacological aspects of 27 individual D-amino acids, D-peptides, and isomeric amino acid derivatives and suggested research needs in each of these areas. The described results provide a valuable record and resource for further progress on the multifaceted aspects of D-amino acids in food and biological samples.

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Section: Isoleucine Stereoisomers (D-ile L-allo-ile and D-allo-ile)mentioning

confidence: 98%

Nutritional and medicinal aspects of d-amino acids

2011

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“…The publications [7][8][9]16,[27][28][29][30][31][32][33][34][35] that appeared in the last decades made a considerable contribution to the concept of molecular structures of amino acids.…”

Section: Crystal Structure Of Amino Acidsmentioning

confidence: 99%

“…7,16,[28][29][30][31][32]41 They systematically studied equimolar compounds composed of molecules of different amino acids using SCXRD techniques. These compounds have been mentioned under various names including "1:1 complexes", 16,29,31,32 "diastereomeric complexes", 30 "pseudoracemic complexes", 41 and "quasiracemates". 7,28 To describe the interactions of different molecules in crystal structures of these compounds, C. H. Görbitz 7 used designations LD-LD and L1-D1 in accordance with the geometry of the hydrogen bonds formed.…”

Section: Crystal Structure Of Equimolar Heterocompounds Of Amino Acidsmentioning

confidence: 99%

Heteromolecular compounds in binary systems of amino acids with opposite and same chiralities

et al. 2020

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“…[84] This is true for the A, C and D polymorphs, while the tetragonal B polymorph has a 3D network. [82] [97-100] The following empirical rules have been deduced [97] for the effect of the side chain: (i) complexes with two linear amino acids have LD-LD patterns; (ii) complexes with two branched amino acids have L1-D1 patterns; (iii) complexes with one linear and one branched amino acid form L1-D1 when the acid with branching is Leu and LD-LD patterns for all other branched amino acids (Val, Ile, Phe, etc.). The only exception to this set of rules is l-Abu:d-Nle, Figure 17, which despite the linear side chains (ethyl and butyl) makes an L1-D1 structure.…”

Section: α-Dialkylated Amino Acidsmentioning

confidence: 99%

Crystal structures of amino acids: from bond lengths in glycine to metal complexes and high-pressure polymorphs

Görbitz

2015

Crystallography Reviews

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After the discovery of X-ray diffraction by crystals, amino acids were among the first organic compounds to have their solid-state structures investigated. The Cambridge Structural Database now contains more than 3500 entries for α-amino acids alone. After a short introduction dealing with the early history of X-ray structure determination, this review provides a classification of amino acid structures, describes essential structural elements, especially hydrogen bonding preferences and coordination to metal ions, and considers recent investigations on phase transitions as the result of extreme temperatures or pressure.

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

Cited by 23 publications

References 8 publications

Nutritional and medicinal aspects of d-amino acids

Nutritional and medicinal aspects of d-amino acids

Heteromolecular compounds in binary systems of amino acids with opposite and same chiralities

Crystal structures of amino acids: from bond lengths in glycine to metal complexes and high-pressure polymorphs

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