Abstract
The effects of small amounts of enantiomeric impurities on the vibrational modes of polycrystalline L-histidine (His) were examined using high-frequency-accurate terahertz (THz) spectroscopy. Samples of polycrystalline L-His in its monoclinic form (form B) were grown from an ethanol-rich solvent. D-histidine, ranging from 0.05 to 10.0% in content, was added to the L-His/ethanol-rich solution prior to recrystallization. The crystal forms of all recrystallized samples were first confirmed by high-frequency-accurate THz spectra recorded at 70 K and room-temperature powder X-ray diffraction spectra. A detailed analysis of two spectral features (1.54 and 1.80 THz) measured at 10 K showed that the absorption lines had a narrow linewidth, as well as broad spectral components that could be fitted by Gaussian curves corresponding to defects within the crystals. The shifts in peak frequency with varying amounts of D-His additive in the polycrystalline L-His samples were examined in detail. It was observed that the peak frequency shifted to lower frequencies when small amounts of D-histidine were present and then to higher frequencies when relatively large amounts were present. At low concentrations, D-His molecules are thought to act as impurities that disturb the normal mode vibrations of L-His crystals; however, above certain concentrations, D-His contributes to the formation of a DL racemic crystal. Although the effects of small amounts of D-His molecules in L-His crystals were detectable, quantitative determination of trace amounts of impurity was limited by the complex crystallography of L-His, which includes defects and racemic compounds.
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References
T. Sasaki, T. Sakamoto and M. Otsuka, Anal. Chem., 90 (2018) 1677–1682.
International Conference on Harmonization; "Impurities in New Drug Substances", (1995).
S. Smith, "Chiral toxicology: it’s the same thing...only different". Toxicological Sciences. 110 (2009) 4–30.
M. Yamaguchi, F. Miyamaru, K. Yamamoto, M. Tani, and M. Hangyo, Appl. Phys. Lett. 86 (2005) 053903.
T. Zhou, Y. Wu, J. Cao, L. Zou, J. Yuan, Z. Yao, and G. Xu, Applied Spectroscopy, 71 (2016) 194–202.
S. Zong, G. Ren, S. Li, B. Zhang, J. Zhang, W. Qi, J. Han, H. Zhao, Journal of Molecular Structure, 1157 (2018) 486–491.
R. Rungsawang, Y. Ueno, I. Tomita, K. Ajito, J. Phys. Chem. B 110, (2006) 21259–21263.
G. Dovbeshkoa, L. Berezhinsky, J. Mol. Struct. 450 (1998) 121–128.
J. Nishizawa, T. Sasaki, K. Suto, M. Ito, T. Yoshida and T. Tanabe, Int. J. Infrared and Millimeter Waves, 29 (2008) 291–297.
A. True, K. Schroeck, T. French, C. Schmuttenmaer, J. Infrared Millim. Terahertz Waves 32 (2011) 691–698.
C. Roelands, S. Jiang, M. Kitamura, J. Horst, H. Kramer, and P. Jansens, Crystal Growth & Design 6 (2006) 955–963.
L. Wantha, N. Punmalee, V. Sawaddiphol, A. Flood, J. Crystal Growth 490 (2018) 65–70.
M. Kitamura, H. Furukawa, M. Asaeda, J. Crystal Growth 141 (1994) 193–199.
T. Sasaki, T. Tanabe and J. Nishizawa, Optics and Photonics Journal, 4 (2014) 8–13.
T. Sasaki, T. Tanabe and J. Nishizawa, J. Jpn. Soc. Infrared Science & Technology, 26 (2016) 74–81.
T. Tanabe, K. Suto, J. Nishizawa, T. Kimura and K. Saito, J. Appl. Phys., 93 (2003) 4610–4615.
T. Tanabe, K. Suto, J. Nishizawa, K. Saito and T. Kimura, J. Phys. D: Appl. Phys., 36 (2003) 953–957.
T. Tanabe, K. Suto, J. Nishizawa, K. Saito and T. Kimura, Appl. Phys. Lett., 83 (2003) 237–239.
J. Madden, E. McGandy, N. Seeman, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 28 (1972) 2377.
J. Madden, E. McGandy, N. Seeman, M. Harding, A. Hoy, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 28 (1972) 2382.
P. Coppens, Y. Abramov, M. Carducci, B. Korjov, I. Novozhilova, C. Alhambra, M. Pressprich, J.Am.Chem.Soc. 121 (1999) 2585.
F. Allen, Acta Crystallogr. B. 58 (2002) 380–388.
A. Stoneham, Reviews of Modern Physics, 41 (1969) 82–108.
Funding
This work was partly supported by a research grant from the Japan Agency for Medical Research and Development (AMED) and Grants-in-Aid for Scientific Research (B) (no. 16H03882) from the Japan Society for the Promotion of Science.
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Sasaki, T., Sakamoto, T. & Otsuka, M. Precise Evaluation of the Effects of a Small Amount of D-histidine in L-histidine Crystal Form B Using High-Frequency-Accurate Terahertz Spectroscopy. J Infrared Milli Terahz Waves 41, 529–541 (2020). https://doi.org/10.1007/s10762-020-00675-5
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DOI: https://doi.org/10.1007/s10762-020-00675-5