Structural Analysis of Crystalline R(+)-α-Lipoic Acid-α-cyclodextrin Complex Based on Microscopic and Spectroscopic Studies
R(+)-α-lipoic acid (RALA) is a naturally-occurring substance, and its protein-bound form plays significant role in the energy metabolism in the mitochondria. RALA is vulnerable to a variety of physical stimuli, including heat and UV light, which prompted us to study the stability of its complexes w...
Ausführliche Beschreibung
Autor*in: |
Naoko Ikuta [verfasserIn] Takatsugu Endo [verfasserIn] Shota Hosomi [verfasserIn] Keita Setou [verfasserIn] Shiori Tanaka [verfasserIn] Noriko Ogawa [verfasserIn] Hiromitsu Yamamoto [verfasserIn] Tomoyuki Mizukami [verfasserIn] Shoji Arai [verfasserIn] Masayuki Okuno [verfasserIn] Kenji Takahashi [verfasserIn] Keiji Terao [verfasserIn] Seiichi Matsugo [verfasserIn] |
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E-Artikel |
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Sprache: |
Englisch |
Erschienen: |
2015 |
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Übergeordnetes Werk: |
In: International Journal of Molecular Sciences - MDPI AG, 2003, 16(2015), 10, Seite 24614-24628 |
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Übergeordnetes Werk: |
volume:16 ; year:2015 ; number:10 ; pages:24614-24628 |
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DOI / URN: |
10.3390/ijms161024614 |
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Katalog-ID: |
DOAJ077850068 |
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520 | |a R(+)-α-lipoic acid (RALA) is a naturally-occurring substance, and its protein-bound form plays significant role in the energy metabolism in the mitochondria. RALA is vulnerable to a variety of physical stimuli, including heat and UV light, which prompted us to study the stability of its complexes with cyclodextrins (CDs). In this study, we have prepared and purified a crystalline RALA-αCD complex and evaluated its properties in the solid state. The results of 1H NMR and PXRD analyses indicated that the crystalline RALA-αCD complex is a channel type complex with a molar ratio of 2:3 (RALA:α-CD). Attenuated total reflection/Fourier transform infrared analysis of the complex showed the shift of the C=O stretching vibration of RALA due to the formation of the RALA-αCD complex. Raman spectroscopic analysis revealed the significant weakness of the S–S and C–S stretching vibrations of RALA in the RALA-αCD complex implying that the dithiolane ring of RALA is almost enclosed in glucose ring of α-CD. Extent of this effect was dependent on the direction of the excitation laser to the hexagonal morphology of the crystal. Solid-state NMR analysis allowed for the chemical shift of the C=O peak to be precisely determined. These results suggested that RALA was positioned in the α-CD cavity with its 1,2-dithiolane ring orientated perpendicular to the plane of the α-CD ring. | ||
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10.3390/ijms161024614 doi (DE-627)DOAJ077850068 (DE-599)DOAJc9e3502a9b8a432f9e0f98c6add4ff9a DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Naoko Ikuta verfasserin aut Structural Analysis of Crystalline R(+)-α-Lipoic Acid-α-cyclodextrin Complex Based on Microscopic and Spectroscopic Studies 2015 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier R(+)-α-lipoic acid (RALA) is a naturally-occurring substance, and its protein-bound form plays significant role in the energy metabolism in the mitochondria. RALA is vulnerable to a variety of physical stimuli, including heat and UV light, which prompted us to study the stability of its complexes with cyclodextrins (CDs). In this study, we have prepared and purified a crystalline RALA-αCD complex and evaluated its properties in the solid state. The results of 1H NMR and PXRD analyses indicated that the crystalline RALA-αCD complex is a channel type complex with a molar ratio of 2:3 (RALA:α-CD). Attenuated total reflection/Fourier transform infrared analysis of the complex showed the shift of the C=O stretching vibration of RALA due to the formation of the RALA-αCD complex. Raman spectroscopic analysis revealed the significant weakness of the S–S and C–S stretching vibrations of RALA in the RALA-αCD complex implying that the dithiolane ring of RALA is almost enclosed in glucose ring of α-CD. Extent of this effect was dependent on the direction of the excitation laser to the hexagonal morphology of the crystal. Solid-state NMR analysis allowed for the chemical shift of the C=O peak to be precisely determined. These results suggested that RALA was positioned in the α-CD cavity with its 1,2-dithiolane ring orientated perpendicular to the plane of the α-CD ring. cyclodextrin lipoic acid ATR/FT-IR microscopic Raman solid-state NMR Biology (General) Chemistry Takatsugu Endo verfasserin aut Shota Hosomi verfasserin aut Keita Setou verfasserin aut Shiori Tanaka verfasserin aut Noriko Ogawa verfasserin aut Hiromitsu Yamamoto verfasserin aut Tomoyuki Mizukami verfasserin aut Shoji Arai verfasserin aut Masayuki Okuno verfasserin aut Kenji Takahashi verfasserin aut Keiji Terao verfasserin aut Seiichi Matsugo verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 16(2015), 10, Seite 24614-24628 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:16 year:2015 number:10 pages:24614-24628 https://doi.org/10.3390/ijms161024614 kostenfrei https://doaj.org/article/c9e3502a9b8a432f9e0f98c6add4ff9a kostenfrei http://www.mdpi.com/1422-0067/16/10/24614 kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 16 2015 10 24614-24628 |
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10.3390/ijms161024614 doi (DE-627)DOAJ077850068 (DE-599)DOAJc9e3502a9b8a432f9e0f98c6add4ff9a DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Naoko Ikuta verfasserin aut Structural Analysis of Crystalline R(+)-α-Lipoic Acid-α-cyclodextrin Complex Based on Microscopic and Spectroscopic Studies 2015 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier R(+)-α-lipoic acid (RALA) is a naturally-occurring substance, and its protein-bound form plays significant role in the energy metabolism in the mitochondria. RALA is vulnerable to a variety of physical stimuli, including heat and UV light, which prompted us to study the stability of its complexes with cyclodextrins (CDs). In this study, we have prepared and purified a crystalline RALA-αCD complex and evaluated its properties in the solid state. The results of 1H NMR and PXRD analyses indicated that the crystalline RALA-αCD complex is a channel type complex with a molar ratio of 2:3 (RALA:α-CD). Attenuated total reflection/Fourier transform infrared analysis of the complex showed the shift of the C=O stretching vibration of RALA due to the formation of the RALA-αCD complex. Raman spectroscopic analysis revealed the significant weakness of the S–S and C–S stretching vibrations of RALA in the RALA-αCD complex implying that the dithiolane ring of RALA is almost enclosed in glucose ring of α-CD. Extent of this effect was dependent on the direction of the excitation laser to the hexagonal morphology of the crystal. Solid-state NMR analysis allowed for the chemical shift of the C=O peak to be precisely determined. These results suggested that RALA was positioned in the α-CD cavity with its 1,2-dithiolane ring orientated perpendicular to the plane of the α-CD ring. cyclodextrin lipoic acid ATR/FT-IR microscopic Raman solid-state NMR Biology (General) Chemistry Takatsugu Endo verfasserin aut Shota Hosomi verfasserin aut Keita Setou verfasserin aut Shiori Tanaka verfasserin aut Noriko Ogawa verfasserin aut Hiromitsu Yamamoto verfasserin aut Tomoyuki Mizukami verfasserin aut Shoji Arai verfasserin aut Masayuki Okuno verfasserin aut Kenji Takahashi verfasserin aut Keiji Terao verfasserin aut Seiichi Matsugo verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 16(2015), 10, Seite 24614-24628 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:16 year:2015 number:10 pages:24614-24628 https://doi.org/10.3390/ijms161024614 kostenfrei https://doaj.org/article/c9e3502a9b8a432f9e0f98c6add4ff9a kostenfrei http://www.mdpi.com/1422-0067/16/10/24614 kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 16 2015 10 24614-24628 |
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10.3390/ijms161024614 doi (DE-627)DOAJ077850068 (DE-599)DOAJc9e3502a9b8a432f9e0f98c6add4ff9a DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Naoko Ikuta verfasserin aut Structural Analysis of Crystalline R(+)-α-Lipoic Acid-α-cyclodextrin Complex Based on Microscopic and Spectroscopic Studies 2015 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier R(+)-α-lipoic acid (RALA) is a naturally-occurring substance, and its protein-bound form plays significant role in the energy metabolism in the mitochondria. RALA is vulnerable to a variety of physical stimuli, including heat and UV light, which prompted us to study the stability of its complexes with cyclodextrins (CDs). In this study, we have prepared and purified a crystalline RALA-αCD complex and evaluated its properties in the solid state. The results of 1H NMR and PXRD analyses indicated that the crystalline RALA-αCD complex is a channel type complex with a molar ratio of 2:3 (RALA:α-CD). Attenuated total reflection/Fourier transform infrared analysis of the complex showed the shift of the C=O stretching vibration of RALA due to the formation of the RALA-αCD complex. Raman spectroscopic analysis revealed the significant weakness of the S–S and C–S stretching vibrations of RALA in the RALA-αCD complex implying that the dithiolane ring of RALA is almost enclosed in glucose ring of α-CD. Extent of this effect was dependent on the direction of the excitation laser to the hexagonal morphology of the crystal. Solid-state NMR analysis allowed for the chemical shift of the C=O peak to be precisely determined. These results suggested that RALA was positioned in the α-CD cavity with its 1,2-dithiolane ring orientated perpendicular to the plane of the α-CD ring. cyclodextrin lipoic acid ATR/FT-IR microscopic Raman solid-state NMR Biology (General) Chemistry Takatsugu Endo verfasserin aut Shota Hosomi verfasserin aut Keita Setou verfasserin aut Shiori Tanaka verfasserin aut Noriko Ogawa verfasserin aut Hiromitsu Yamamoto verfasserin aut Tomoyuki Mizukami verfasserin aut Shoji Arai verfasserin aut Masayuki Okuno verfasserin aut Kenji Takahashi verfasserin aut Keiji Terao verfasserin aut Seiichi Matsugo verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 16(2015), 10, Seite 24614-24628 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:16 year:2015 number:10 pages:24614-24628 https://doi.org/10.3390/ijms161024614 kostenfrei https://doaj.org/article/c9e3502a9b8a432f9e0f98c6add4ff9a kostenfrei http://www.mdpi.com/1422-0067/16/10/24614 kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 16 2015 10 24614-24628 |
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10.3390/ijms161024614 doi (DE-627)DOAJ077850068 (DE-599)DOAJc9e3502a9b8a432f9e0f98c6add4ff9a DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Naoko Ikuta verfasserin aut Structural Analysis of Crystalline R(+)-α-Lipoic Acid-α-cyclodextrin Complex Based on Microscopic and Spectroscopic Studies 2015 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier R(+)-α-lipoic acid (RALA) is a naturally-occurring substance, and its protein-bound form plays significant role in the energy metabolism in the mitochondria. RALA is vulnerable to a variety of physical stimuli, including heat and UV light, which prompted us to study the stability of its complexes with cyclodextrins (CDs). In this study, we have prepared and purified a crystalline RALA-αCD complex and evaluated its properties in the solid state. The results of 1H NMR and PXRD analyses indicated that the crystalline RALA-αCD complex is a channel type complex with a molar ratio of 2:3 (RALA:α-CD). Attenuated total reflection/Fourier transform infrared analysis of the complex showed the shift of the C=O stretching vibration of RALA due to the formation of the RALA-αCD complex. Raman spectroscopic analysis revealed the significant weakness of the S–S and C–S stretching vibrations of RALA in the RALA-αCD complex implying that the dithiolane ring of RALA is almost enclosed in glucose ring of α-CD. Extent of this effect was dependent on the direction of the excitation laser to the hexagonal morphology of the crystal. Solid-state NMR analysis allowed for the chemical shift of the C=O peak to be precisely determined. These results suggested that RALA was positioned in the α-CD cavity with its 1,2-dithiolane ring orientated perpendicular to the plane of the α-CD ring. cyclodextrin lipoic acid ATR/FT-IR microscopic Raman solid-state NMR Biology (General) Chemistry Takatsugu Endo verfasserin aut Shota Hosomi verfasserin aut Keita Setou verfasserin aut Shiori Tanaka verfasserin aut Noriko Ogawa verfasserin aut Hiromitsu Yamamoto verfasserin aut Tomoyuki Mizukami verfasserin aut Shoji Arai verfasserin aut Masayuki Okuno verfasserin aut Kenji Takahashi verfasserin aut Keiji Terao verfasserin aut Seiichi Matsugo verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 16(2015), 10, Seite 24614-24628 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:16 year:2015 number:10 pages:24614-24628 https://doi.org/10.3390/ijms161024614 kostenfrei https://doaj.org/article/c9e3502a9b8a432f9e0f98c6add4ff9a kostenfrei http://www.mdpi.com/1422-0067/16/10/24614 kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 16 2015 10 24614-24628 |
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International Journal of Molecular Sciences |
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Naoko Ikuta Takatsugu Endo Shota Hosomi Keita Setou Shiori Tanaka Noriko Ogawa Hiromitsu Yamamoto Tomoyuki Mizukami Shoji Arai Masayuki Okuno Kenji Takahashi Keiji Terao Seiichi Matsugo |
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Elektronische Aufsätze |
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Naoko Ikuta |
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structural analysis of crystalline r(+)-α-lipoic acid-α-cyclodextrin complex based on microscopic and spectroscopic studies |
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Structural Analysis of Crystalline R(+)-α-Lipoic Acid-α-cyclodextrin Complex Based on Microscopic and Spectroscopic Studies |
abstract |
R(+)-α-lipoic acid (RALA) is a naturally-occurring substance, and its protein-bound form plays significant role in the energy metabolism in the mitochondria. RALA is vulnerable to a variety of physical stimuli, including heat and UV light, which prompted us to study the stability of its complexes with cyclodextrins (CDs). In this study, we have prepared and purified a crystalline RALA-αCD complex and evaluated its properties in the solid state. The results of 1H NMR and PXRD analyses indicated that the crystalline RALA-αCD complex is a channel type complex with a molar ratio of 2:3 (RALA:α-CD). Attenuated total reflection/Fourier transform infrared analysis of the complex showed the shift of the C=O stretching vibration of RALA due to the formation of the RALA-αCD complex. Raman spectroscopic analysis revealed the significant weakness of the S–S and C–S stretching vibrations of RALA in the RALA-αCD complex implying that the dithiolane ring of RALA is almost enclosed in glucose ring of α-CD. Extent of this effect was dependent on the direction of the excitation laser to the hexagonal morphology of the crystal. Solid-state NMR analysis allowed for the chemical shift of the C=O peak to be precisely determined. These results suggested that RALA was positioned in the α-CD cavity with its 1,2-dithiolane ring orientated perpendicular to the plane of the α-CD ring. |
abstractGer |
R(+)-α-lipoic acid (RALA) is a naturally-occurring substance, and its protein-bound form plays significant role in the energy metabolism in the mitochondria. RALA is vulnerable to a variety of physical stimuli, including heat and UV light, which prompted us to study the stability of its complexes with cyclodextrins (CDs). In this study, we have prepared and purified a crystalline RALA-αCD complex and evaluated its properties in the solid state. The results of 1H NMR and PXRD analyses indicated that the crystalline RALA-αCD complex is a channel type complex with a molar ratio of 2:3 (RALA:α-CD). Attenuated total reflection/Fourier transform infrared analysis of the complex showed the shift of the C=O stretching vibration of RALA due to the formation of the RALA-αCD complex. Raman spectroscopic analysis revealed the significant weakness of the S–S and C–S stretching vibrations of RALA in the RALA-αCD complex implying that the dithiolane ring of RALA is almost enclosed in glucose ring of α-CD. Extent of this effect was dependent on the direction of the excitation laser to the hexagonal morphology of the crystal. Solid-state NMR analysis allowed for the chemical shift of the C=O peak to be precisely determined. These results suggested that RALA was positioned in the α-CD cavity with its 1,2-dithiolane ring orientated perpendicular to the plane of the α-CD ring. |
abstract_unstemmed |
R(+)-α-lipoic acid (RALA) is a naturally-occurring substance, and its protein-bound form plays significant role in the energy metabolism in the mitochondria. RALA is vulnerable to a variety of physical stimuli, including heat and UV light, which prompted us to study the stability of its complexes with cyclodextrins (CDs). In this study, we have prepared and purified a crystalline RALA-αCD complex and evaluated its properties in the solid state. The results of 1H NMR and PXRD analyses indicated that the crystalline RALA-αCD complex is a channel type complex with a molar ratio of 2:3 (RALA:α-CD). Attenuated total reflection/Fourier transform infrared analysis of the complex showed the shift of the C=O stretching vibration of RALA due to the formation of the RALA-αCD complex. Raman spectroscopic analysis revealed the significant weakness of the S–S and C–S stretching vibrations of RALA in the RALA-αCD complex implying that the dithiolane ring of RALA is almost enclosed in glucose ring of α-CD. Extent of this effect was dependent on the direction of the excitation laser to the hexagonal morphology of the crystal. Solid-state NMR analysis allowed for the chemical shift of the C=O peak to be precisely determined. These results suggested that RALA was positioned in the α-CD cavity with its 1,2-dithiolane ring orientated perpendicular to the plane of the α-CD ring. |
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title_short |
Structural Analysis of Crystalline R(+)-α-Lipoic Acid-α-cyclodextrin Complex Based on Microscopic and Spectroscopic Studies |
url |
https://doi.org/10.3390/ijms161024614 https://doaj.org/article/c9e3502a9b8a432f9e0f98c6add4ff9a http://www.mdpi.com/1422-0067/16/10/24614 https://doaj.org/toc/1422-0067 |
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Takatsugu Endo Shota Hosomi Keita Setou Shiori Tanaka Noriko Ogawa Hiromitsu Yamamoto Tomoyuki Mizukami Shoji Arai Masayuki Okuno Kenji Takahashi Keiji Terao Seiichi Matsugo |
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Takatsugu Endo Shota Hosomi Keita Setou Shiori Tanaka Noriko Ogawa Hiromitsu Yamamoto Tomoyuki Mizukami Shoji Arai Masayuki Okuno Kenji Takahashi Keiji Terao Seiichi Matsugo |
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