Crystal structures of three halide salts of <scp>L</scp>-asparagine: an isostructural series

Moraes, Lygia Silva de; Kennedy, Alan R.; Logan, Charlie R.

doi:10.1107/s2056989018014603

Cited by 2 publications

(3 citation statements)

References 18 publications

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“…However, the crystal structures of the triacetate bromide salt ( 4 ) and its thioamide derivative 5 are non-isostructural. The fact that chloride and bromide salts can form isostructural crystal structures is quite well-known, see, e.g., refs and for two examples. The question remains: why does the substitution of the carbonyl oxygen with a sulfur atom to yield a thioamide give rise to an isostructural structure in the case of salt 3 but not for 5 ?…”

Section: Resultsmentioning

confidence: 99%

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Nicotinamide Riboside Derivatives: Single Crystal Growth and Determination of X-ray Structures

Álvarez

Schabert²,

Soydemir³

et al. 2019

Crystal Growth & Design

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For the first time, the X-ray structure of nicotinamide riboside could be determined. Five nicotinamide riboside (NR) derivatives in their native, thioamide and triacetyl protected form could be crystallized as their chloride and bromide salts. The single crystals were obtained with the help of the vapor diffusion technique. The use of the much slower layering technique for crystallization led to the decomposition of the nicotinamide ribosides yielding the corresponding nicotinamide salts. The torsion angles of the five nicotinamide riboside derivatives were compared with those obtained from the two nicotinamide adenine dinucleotide crystal and the three protein nicotinamide riboside cocrystal structures.

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Section: Resultsmentioning

confidence: 99%

“…The fact that chloride and bromide salts can form isostructural crystal structures is quite well known, see e.g. references 16,17 for two examples. It remains the question, why the substitution of the carbonyl oxygen with a sulfur atom to yield a thioamide gives raise to an isostructural structure in the case of salt 3 but not for 5?…”

Section: Isostructuralitymentioning

confidence: 99%

Nicotinamide Riboside Derivatives: Single Crystal Growth and Determination of X-ray Structures

Álvarez

Schabert²,

Soydemir³

et al. 2019

Crystal Growth & Design

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“…The effect of halogen substitution on the resulting crystal structure has been explored previously. Three halide salts of lasparagine monohydrate C 4 H 9 N 2 O 3 + ÁX À ÁH 2 O, where X = Cl, Br, and I, have also been determined (CSD refcodes LIRLUW, LIRMAD, and LIRMEH; de Moraes et al, 2018), representing a similar organic small-molecule halide series. However, all three of the halide salts were determined to be isostructural, in contrast to our results.…”

Section: Database Surveymentioning

confidence: 99%

Crystal structures of three β-halolactic acids: hydrogen bonding resulting in differing Z′

Gordon¹,

Liu²,

Shafei³

et al. 2022

Acta Crystallogr C Struct Chem

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The crystal structures of three β-halolactic acids have been determined, namely, β-chlorolactic acid (systematic name: 3-chloro-2-hydroxypropanoic acid, C3H5ClO3) (I), β-bromolactic acid (systematic name: 3-bromo-2-hydroxypropanoic acid, C3H5BrO3) (II), and β-iodolactic acid (systematic name: 2-hydroxy-3-iodopropanoic acid, C3H5IO3) (III). The number of molecules in the asymmetric unit of each crystal structure (Z′) was found to be two for I and II, and one for III, making I and II isostructural and III unique. The difference between the molecules in the asymmetric units of I and II is due to the direction of the hydrogen bond of the alcohol group to a neighboring molecule. Molecular packing shows that each structure has alternating layers of intermolecular hydrogen bonding and halogen–halogen interactions. Hirshfeld surfaces and two-dimensional fingerprint plots were analyzed to further explore the intermolecular interactions of these structures. In I and II, energy minimization is achieved by lowering of the symmetry to adopt two independent molecular conformations in the asymmetric unit.

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Crystal structures of three halide salts of L-asparagine: an isostructural series

Abstract: The monohydrated chloride, bromide and iodide salt forms of the amino acid l-asparagine form an isostructural series.

Cited by 2 publications

References 18 publications

Nicotinamide Riboside Derivatives: Single Crystal Growth and Determination of X-ray Structures

Nicotinamide Riboside Derivatives: Single Crystal Growth and Determination of X-ray Structures

Crystal structures of three β-halolactic acids: hydrogen bonding resulting in differing Z′

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