Molecular Complex of Lumiflavin and 2-Aminobenzoic Acid : Crystal Structure, Crystal Spectra, and Solution Properties

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1981
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Shieh, Huey-Sheng
Hanson, Louise Karle
Ludwig, Martha L.
Nordman, Christer E.
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The molecular complex lumiflavin-2-aminobenzoic acid monohydrate (C13H12N402●C7H7N02●H2O)crystallizes from aqueous solution as red triclinic prisms. The space group is P1 with cell dimensions a = 9.660 A, b = 14.866 Å, c = 7.045 Å, α = 95.44°, β = 95.86°, and γ = 105.66°. The crystal structure was solved by direct methods and refined by block-diagonal least-squares procedures to an R value of 0.050 on the basis of 1338 observed reflections. The structure is composed of stacks of alternating lumiflavin and un-ionized (neutral) 2-aminobenzoic acid molecules. Two different modes of stacking interaction are observed. In one, 2-aminobenzoic acid overlaps all three of the isoalloxazine rings, at a mean distance of 3.36 Å; in the other, 2-aminobenzoic acid interacts with the pyrazine and dimethylbenzene moieties, at a distance of 3.42 Å. Perpendicular to the stacking direction, the molecules form a continuous sheet. Each flavin is hydrogen bonded via O(2) and NH(3) to two symmetrically related aminobenzoates; the water of crystallization forms three hydrogen bonds, bridging two flavins, via O(4) and N(5), and one aminobenzoic acid. The red color of the crystals results from a charge-transfer transition involving stacked flavin and 2-aminobenzoic acid molecules. Measurements of the polarized optical absorption spectra of crystals show that the transition moment direction for the long wavelength absorbance (beyond 530 nm) contains an out-of-plane component which can only arise from a charge-transfer interaction. Since the amino N does not make exceptionally close interactions with isoalloxazine atoms in either stacking mode (minimum interatomic distance 3.52 Å), the charge transfer is presumed to involve Pi orbitals of the 2-aminobenzoic acid donor.

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ISO 690SHIEH, Huey-Sheng, Sandro GHISLA, Louise Karle HANSON, Martha L. LUDWIG, Christer E. NORDMAN, 1981. Molecular Complex of Lumiflavin and 2-Aminobenzoic Acid : Crystal Structure, Crystal Spectra, and Solution Properties. In: Biochemistry. 1981, 20(16), pp. 4766-4774. ISSN 0006-2960. eISSN 1520-4995. Available under: doi: 10.1021/bi00519a037
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@article{Shieh1981Molec-6876,
  year={1981},
  doi={10.1021/bi00519a037},
  title={Molecular Complex of Lumiflavin and 2-Aminobenzoic Acid : Crystal Structure, Crystal Spectra, and Solution Properties},
  number={16},
  volume={20},
  issn={0006-2960},
  journal={Biochemistry},
  pages={4766--4774},
  author={Shieh, Huey-Sheng and Ghisla, Sandro and Hanson, Louise Karle and Ludwig, Martha L. and Nordman, Christer E.}
}
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