Hygric acid (I) and stachydrine (II) as their hydrochlorides

Jones, Graham; Naidu, BP; Paleg, L. G.; Tiekink, Edward R. T.

doi:10.1107/s0108270188005372

Cited by 3 publications

(3 citation statements)

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“…The 1,6-dideoxy-a-L-fructofuranose in 2 also has no significant deviations in the mean bond distances (1.523 Å and 1.421 Å correspondingly) from those determined for the b-fructopyranose in 1, the b-fructofuranose in L-rhamnulose-dibenzylamine, [35] and the averaged values for furanose structures. [40,47] In the proline part of both 1 and 2, the N1-C7 bond (Table 3) is about 0.04 Å longer than respective bonds in a number of known proline structures, [41,43,45,48] while the rest of the bond lengths compare well. Differences were observed with respect to the carboxyl-oxygen bond lengths for 1 and 2.…”

Section: Bond Distancesmentioning

confidence: 86%

“…For the comparison, the envelope ring conformations close to that in 1 have been reported for proline residues in some crystalline peptides, [41] while the twisted ring conformation in 2 is closer to those found in crystals of Lproline, [42] DL-proline, [43] and small peptides. [41] In contrast, the pyrrolidine ring in N-methyl-L-proline (hygric acid) monohydrate [44] or hydrochloride [45] accepts rare C 2 -N-endo conformations.…”

Section: Ring Conformationsmentioning

confidence: 90%

“…[39] Torsion angles in the amino acid portions of 1 and 2 do not differ more than 258: the most significant conformational difference between the proline residues is observed around the N1-C7 bond ( Table 3). The carboxylate C11 carbons are in trans configuration relative to the carbohydrate C1 atoms and V. V. Mossine et al are in eclipsed, anti-synclinal conformation around the N1-C7 bond (distorted by 458 and 538 relative to the staggered structure in, correspondingly, 1 and 2); the respective trans configurations were found around N-Ca bonds in crystalline N-methyl-L-proline [44,45] as well.…”

Section: Torsion Anglesmentioning

confidence: 94%

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The Structure of N‐(1‐Deoxy‐β‐D‐fructopyranos‐1‐yl)‐L‐proline Monohydrate (“D‐Fructose‐L‐proline”) and N‐(1,6‐Dideoxy‐α‐L‐fructofuranos‐1‐yl)‐L‐proline (“L‐Rhamnulose‐L‐proline”)

Mossine

Barnes

Mawhinney

2007

Journal of Carbohydrate Chemistry

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D-Fructose-L-proline is an important food-related precursor for thermally generated aromas. We report the crystal structure analysis of N-(1-deoxy-b-D-fructopyranos-1-yl)-L-proline monohydrate (1) and its analog, N-(1,6-dideoxy-a-L-fructofuranos-1-yl)-L-proline ("L-rhamnulose-L-proline") (2). The carbohydrate rings adopt the normal 2 C 5 pyranose chair conformation in 1 and the 5 E furanose envelope conformation in 2. Bond lengths and valence angles in 1 and 2 compare well with the average values from related pyranose and furanose structures. All hydroxyl and carboxyl oxygen atoms, ammonium groups, and the water molecule in 1 are involved in an extensive hydrogen bonding, which forms a system of infinite chains with attached side chains.The hydrogen bonding network in 2 is an infinite three-dimensional network and is represented by separate short finite and infinite chains.

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Section: Bond Distancesmentioning

confidence: 86%

Section: Ring Conformationsmentioning

confidence: 90%

Section: Torsion Anglesmentioning

confidence: 94%

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The Structure of N‐(1‐Deoxy‐β‐D‐fructopyranos‐1‐yl)‐L‐proline Monohydrate (“D‐Fructose‐L‐proline”) and N‐(1,6‐Dideoxy‐α‐L‐fructofuranos‐1‐yl)‐L‐proline (“L‐Rhamnulose‐L‐proline”)

Mossine

Barnes

Mawhinney

2007

Journal of Carbohydrate Chemistry

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Crystal Lattice Energy of Aminoacid Hydrohalides

Rulewski

Skurski

Dokurno

et al. 1996

Molecular Crystals and Liquid Crystals Science and Technology.

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Basic relationships concerning thermodynamics of crystalline phases and the process of their formation, as well as energetics of intermolecular interactions in these, were invoked and discussed from the point of view of their application in studies of stability, features and behaviour of solid systems. Further, electrostatic, dispersive and repulsive contributions to the crystal lattice energy of 25 hydrohalides of aminoacids were calculated assuming that each atom of the basic stoichiometric unit interacts with all atoms from surroundings. Energy of electrostatic interactions was obtained assuming 1+ and 1-charges on cation and anion, respectively, and using atomic partial charges resulting from Mulliken population analysis or fitted so as to reproduce molecular electrostatic potential (MEP) around molecules, determined on ab initio Hartree-Fock (HF) or density functional theory (DFT) levels. Dispersive and repulsive contributions were evaluated by either Lennard-Jones or Buckingham equations using atomic (ionic) parameters for dispersive interactions originating from the London or Slater-Kirkwood theory and those for repulsive interactions resulting from the criterion of minimization of energy on separation of atoms (ions) equal to the s u m of their van der Waals radii. Coulombic energies arising from charges fitted to MEP seem to be the most reliable. These values show a decreasing tendency with an increase of dimensions of ions (volume of basic stoichiometric units).

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