2007 Fiscal Year Final Research Report Summary
Application studies on vibrational circular dichroism as the chiroptical tool
| Project/Area Number |
16310144
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Living organism molecular science
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| Research Institution | Hokkaido University |
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Principal Investigator |
MONDE Kenji Hokkaido University, Faculty of Advanced Life Science, Dr. Associate Professor (40210207)
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| Co-Investigator(Kenkyū-buntansha) |
MIURA Nobuaki okkaido University, Faculty of Advanced Life Science, Dr. Research Associate Professor (80372267)
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| Project Period (FY) |
2004 – 2007
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| Keywords | VCD / vibrational circular dichroism / glycoside bond / stereochemistry / enzymatic reaction monitoring / conformational analysis / absolute configuration / DFT calculation |
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| Research Abstract |
Structural studies of carbohydrates have required development of analytical tools. VCD spectroscopy has been of potential use, but its application to carbohydrates has been limited compared to proteins and nucleic acids partly due to the difficulties in the interpretation of the spectra. Through the systematical carbohydrate measurements, we have found an intense VCD peak appeared around 1145 cm^<-1> characteristic for axial glycosidic sugars i.e. the glycoside band. Isotope substitution indicated the profound participation of the anomeric moiety in the vibration of this band. To predict its vibrational mode by means of density functional theory (DFT) calculation, properly designed model compounds were prepared and their calculated spectra were compared with the observed ones. In this study, for the first time, carbohydrate VCD spectra were reliably predicted. Furthermore, the sign of the glycoside band was found to reflect not only the anomeric configuration but also the pyranose conf
… More
ormation. The isotropic and theoretical studies characterized its vibrational mode as the C1-H1 deformation coupled with C1-O1 stretching, which indicated the applicability to more complicated glycoconjugates. Finally, VCD technique was first applied to glycopeptides, and demonstrated the simultaneous analysis on both the carbohydrate and aglycan parts.
Systematic VCD studies of N-acetylneuraminic acid (Neu5Ac), a recognition related unique carbohydrate, were performed for the first time. Two pairs of anomeric isomers regarding a quaternary C2 asymmetric carbon of Neu5Ac derivatives were synthesized. VCD spectral patterns around the ester carbonyl region, as well as other Mid-IR regions would be practical markers to distinguish the C2 stereochemistry.
Other applications of the VCD technique were also applied to biologically active compounds such as chiral cruciferous phytoalexins and the antidote like compound against snake venom ((+)-alternamin), leading to successful assignments of their stereochemistries in solution station with the aids of their DFT theoretical calculations. Less
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Research Products
(54 results)
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[Journal Article] A structure and an absolute configuration of (+)-alternamin, a new coumarin from Murraya alternans having antidote activity against snake venom2007
Author(s)
Min, H. M., Aye, M., Taniguchi, T., Miura, N., Monde, K., Ohzawa, K., Nikai, T., Niwa, M., Takaya, Y.
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Journal Title
Tetrahedron Lett. 48
Pages: 6155-6158
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] (R)-(+)-[VCD(+)945]-4-Ethyl-4-methyloctane, the Simplest Chiral Saturated Hydrocarbon with a Quaternary Stereogenic Center2007
Author(s)
Fujita, T., Obata, K., Kuwahara, S., Miura, N., Nakahashi, A., Monde, K., Decatur, J., Harada, N.
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Journal Title
Tetrahedron Lett. 48
Pages: 4219-4222
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] Rewinding of Helical Systems by Use of Cr(III) Complex as a Photoresponsive Chiral Dopant2006
Author(s)
Taniguchi, T., Sato, H., Monde, K., Nishimura, S. -I., Yoshida, J., Yamagishi, A.
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Journal Title
Mol. Cryst. Liq. Cryst. 460
Pages: 107-116
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] High Throughput Protein Glycomics: Combined Use of Chemoselective Glycoblotting and MALDI-TOF/TOF Mass Spectrometry2005
Author(s)
Nishimura, S. -I., Niikura, K., Kurogochi, M., Matsushita, T., Fumoto, M. Hinou, H., Kamitani, R., Deguchi, K., Miura, N., Monde, K., Kondo, H.
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Journal Title
Angew. Chem., Int. Ed. 44
Pages: 91-96
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] Sequential Glycoproteins: Practical Feasibility of chitosan-based hyaluronic acid hybrid biomaterial for a novel scaffold in cartilage tissue engineering2005
Author(s)
Yamane, S., Iwasaki, N., Majima, T., Funakoshi, T., Masuko, T., Harada, K., Minami, A., Monde, K., Nishimura, S. -I.
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Journal Title
Biomaterials 26
Pages: 611-619
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] Chiral Cruciferous Phytoalexins: Preparation, Absolute Configuration, and Biological Activity2005
Author(s)
Monde, K., Taniguchi, T., Miura, N., Kutschy, P., Curillova, Z., Pilatova, M., Mojzis, J.
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Journal Title
Bioorg. Med. Chem. 13
Pages: 5206-5212
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] Assignment and quantification of 2-aminopyridine derivatized oligosaccharide isomers coeluted on reverse-phase HPLC/MS by MS^n spectral library2004
Author(s)
Takegawa, Y., Deguchi, K., Ito, S., Yoshioka, S., Sano, A., Yoshinari, K., Kobayashi, K., Nakagawa, H., Monde, K., Nishimura, S. -I.
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Journal Title
Anal. Chem. 76
Pages: 7294-7303
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] Glyco-Insulins: Dendritic sialyloligosaccharide-displaying insulins showing a prolonged blood-sugar lowering activity2004
Author(s)
Sato, M., Furuike, T., Sadamoto, R., Fujitani, N., Nakahara, T., Niikura, K., Monde, K., Kondo, H., Nishimura, S. -I.
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Journal Title
J. Am. Chem. Soc. 126
Pages: 14013-14022
Description
「研究成果報告書概要(欧文)」より
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[Book] 化学と生物2007
Author(s)
門出 健次
Total Pages
455-458
Publisher
日本農芸化学会
Description
「研究成果報告書概要(和文)」より
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[Book] 高分子2006
Author(s)
門出 健次
Total Pages
4
Publisher
高分子学会
Description
「研究成果報告書概要(和文)」より
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