Structure of the <i>D</i> form of <scp>DL</scp>-α-amino-<i>n</i>-butyric acid

Nakata, Kazuaki; Takaki, Y.; Sakurai, Kiichi

doi:10.1107/s056774088000369x

Cited by 23 publications

(22 citation statements)

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“…The crystal structures of amino acids with hydrophobic side chains invariably incorporate molecular bilayers, each with a hydrogen-bonded core and two surfaces shaped by the amino acid side chains. A series of unique solid-state phase transitions, involving sliding along the hydrophobic interfaces between adjacent bilayers, have been observed for dlmethionine (Met; Mathieson, 1952;Taniguchi et al, 1980;Alagar et al, 2005;Gö rbitz et al, 2014; Gö rbitz, 2014), dl-2-aminobutyric acid (Abu; Gö rbitz et al, 2012; Nakata et al, 1980;Voogd & Derissen, 1980;Akimoto & Iitaka, 1972;Ichikawa & Iitaka, 1968), dl-norvaline (Nva; Gö rbitz, 2011) and dl-norleucine (Nle; Coles et al, 2009;Harding et al, 1995;Dalhus & Gö rbitz, 1996b;Smets et al, 2015;van den Ende & Cuppen, 2014) as well as for the four quasiracemates l-Nva:d-Nle, l-Nva:d-Met, l-Nle:d-Met (Gö rbitz & Karen, 2015) and l-Abu:d-Met (Gö rbitz et al, 2016). Little is known by comparison about the corresponding enantiomeric amino acids.…”

Section: Introductionmentioning

confidence: 99%

An exceptional series of phase transitions in hydrophobic amino acids with linear side chains

Görbitz

Karen

Dušek

et al. 2016

IUCrJ

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Section: Introductionmentioning

confidence: 99%

An exceptional series of phase transitions in hydrophobic amino acids with linear side chains

Görbitz

Karen

Dušek

et al. 2016

IUCrJ

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“…Our attention is called to the isomers of the α aminobutyric acid. Four structural modifications are described for the DLa amino-n-butyric acid Akimoto et al, 1972;Voogd et al, 1980;Nakata et al, 1980). One structural modification is pointed out for the α-amino-isobutyric acid (Hirokawa et al, 1952).…”

Section: Introductionmentioning

confidence: 99%

Syntheses and crystal structures of α methyl alaninium dihydrogen monophosphate and Lβ methyl alaninium dihydrogen monophosphate. An approach for the design and preparation of polar organic-inorganic materials

Masse¹,

Durif²

1990

Zeitschrift Für Kristallographie - Crystalline Materials

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The two following salts have been prepared [(CH 3 ) 2 C(NH 3 )-COOH] + · H 2 P04 (aMADP) and [CH 3 CH 2 CH(NH 3 )COOH] + · H 2 PC>4 (L0MADP). The crystal parameters are: a = 10.060(2), b = 7.634(2), c = 5.852(2) Ä, α = 97.32°(5), β = 107.50°(5), y = 81.16°(5); Z=2; Pi for aMADP and a = 7.164(2), b = 6.533(2), c = 9.458(2) Α; β = 105.48°(7); Ζ = 2; P2i for L/?MADP. Crystal structures were solved by direct methods and refined to a final R value 0.026 with 2889 independent data for aMADP and to R = 0.033 with 2027 reflexions for L/JMADP. Hydrogen atoms located by difference-Fourier syntheses were refined. The layer structure of aMADP and the chain structure of L/?MADP emphasize the importance of H2PO4 polymeric anion and its possible use in the design of polar inorganic materials. The effect of chirality on the anion-aggregation, through the hydrogen bonds, clearly indicated by the L/JMADP structure and some others already described, may be easily transposed to individual, cylic, chain or layer inorganic oxoanions.

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“…The racemate, dl-Abu, has a tetragonal polymorph (B) with hydrophobic columns (Voogd & Hulscher, 1980) as well as three known monoclinic polymorphs A, Fig. 1(c) (Voogd & Derissen, 1980), C (Akimoto & Iitaka, 1972) and D (Nakata et al, 1980) that are all divided into layers. The hydrophobic layers in these structures are among the thinnest found for amino acid structures.…”

Section: Introductionmentioning

confidence: 99%

L-2-Aminobutyric acid: two fully ordered polymorphs withZ′ = 4

Görbitz

2010

Acta Crystallogr Sect B

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The crystal structure of L-2-aminobutyric acid, an L-alanine analogue with an ethyl rather than a methyl side chain, has proved elusive owing to problems growing diffraction quality crystals. Good diffraction data have now been obtained for two polymorphs, in space groups P2(1) and I2, revealing surprisingly complex, yet fully ordered crystalline arrangements with Z' = 4. The closely related structures are divided into hydrophilic and hydrophobic layers, the latter being the thinnest ever found for an amino acid (other than alpha-glycine). The hydrophobic layers furthermore contain conspicuous pseudo-centers-of-symmetry, leading to overall centrosymmetric intensity statistics. Uniquely, the four molecules in the asymmetric unit can be divided into two pairs that each forms an independent hydrogen-bond network.

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Structure of the D form of DL-α-amino-n-butyric acid

Cited by 23 publications

References 1 publication

An exceptional series of phase transitions in hydrophobic amino acids with linear side chains

An exceptional series of phase transitions in hydrophobic amino acids with linear side chains

Syntheses and crystal structures of α methyl alaninium dihydrogen monophosphate and Lβ methyl alaninium dihydrogen monophosphate. An approach for the design and preparation of polar organic-inorganic materials

L-2-Aminobutyric acid: two fully ordered polymorphs withZ′ = 4

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