Development of Novel Glycosylation Reaction Using Odorless Benzenethiols
| Project/Area Number |
20590022
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Suzuka University of Medical Science |
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Principal Investigator |
KAJIMOTO Tetsuya Suzuka University of Medical Science, 薬学部, 教授(特任) (80185777)
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| Co-Investigator(Kenkyū-buntansha) |
野出 學 京都薬科大学, 薬学部, 教授 (60027076)
小関 稔 京都薬科大学, 薬学部, 助教 (40465597)
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| Project Period (FY) |
2008 – 2010
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| Project Status |
Completed (Fiscal Year 2010)
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| Budget Amount *help |
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2010: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2009: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2008: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
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| Keywords | p-オクチルオキシベンゼンチオール / 無臭ベンゼンチオール / グリコシル化反応 / 1-チオ-D-グルコサミニド / N-アセチルグルコサミン転移酵素V / NIS / TfOH / PPh3 / CCl4 / CH3CN試薬系 / 非還元末端からの糖鎖合成 / p-ドデシルベンゼンチオール / NIS/TsOH / PPh_3/CCl_4/CH_3CN試薬系 / p-ドデシルフェニルスルホキシル基 / TsOH / PPh_3 / CCl_4 / CH_3CN試薬系 / チオグリコシド / N-アセチルグルコサミン転移酵素-V / セラミド類似体 / アグリコン / ο-ニトロベンジル基 |
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| Research Abstract |
p-Octyloxybenzenethiol (1) was first synthesized as a new odorless benzenethiol. Using 1, 1-(p-octyloxy)phenyl-thio-glycosides (2) were prepared as a new type of glycosyl donors in the glycosylation reaction. After trying the glycosylation reactions under several conditions, it was found that 2 were excellent glycosyl donors in glycosylation reaction activated with N-iodosuccinimide and triflic acid. All the procedure from the preparation of 2 to the glycosylation reaction could be attained completely under conditions where no malodorous stench was generated.
Next, another glycosylation reaction was performed using a combination of 2 and 1-(p-octyloxy)phenyl glycosyl sulfoxides (3), which were prepared by the oxidation of 2, as a glycosyl donor and an acceptor, respectively. Promising results were obtained when p-octyloxylphenyl N-phthalimido-D-thio-glucosaminide derivative was activated with NIS and TfOH for the glycosylation of 3 carrying a free hydroxyl group, especially, at the C-6 position. Successive reduction of the resulting disaccharyl sulfoxides with Ph_3P/CBr_4/CH_3CN provided the corresponding thio-glycosides, which could be used as the glycosyl donors in a following glycosylation reaction to afford trisaccharides in good yield. Using the present method, 4-iodo-phenylalkyl ss-D-N-acetylglucosaminyl-(1-2)-ss-D- mannopyranosyl(1-6)-α-D-glucopyranoside (4), which was designed as a monitoring glycoconjugate for the activity of malignant tumor specific N-acetyl-D-glucosaminyltransferase-V.
Finally, it is noteworthy that the glycosylation reaction using a combination of 2 and 3, which was developed in the present study, provided a novel and useful synthetic method of oligosaccharides, i. e., the glycosylation reaction from the non-reducing ends.
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Report
(4 results)
Research Products
(32 results)
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[Journal Article] Synthesis and Evaluation of a Radioiodinated Trisaccharide Derivative as a Synthetic Substrate for Sensitive N-Acetylglucosaminyltransferase V Radioassay2011
Author(s)
T.Mukai, M.Hagimori, K.Arimitsu, T.Katoh, M.Ukon, T.Kajimoto, H.Kimura, Y.Magata, E.Miyoshi, N.Taniguchi, M.Node, H.Saji
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Journal Title
Bioorg.Med.Chem. (in press)
NAID
Related Report
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[Journal Article] Synthesis and evaluation of a radioiodinated trisaccharide deriv-ative as a synthetic substrate for sensitive N-acetylglucosaminyl-transferase Vradiossay2011
Author(s)
T.Mukai, M.Hagimori, K.Ari-mistsu, T.Katoh, M.Ukon, Y.Magata, E.Miyoshi, N.Tanigu-chi, M.Node, T.Kajimoto, H.Saji
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Journal Title
Bioorg.Med.Chem.
Volume: (In press)
Related Report
Peer Reviewed
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[Journal Article] Efficient total synthesis of (+)-negamycin, a potential chemotherapeutic agent for genetic diseases2008
Author(s)
Y. Hayashi, T. Regnier, S. Ni-shiguchi, M. O. Sydnes, D. Ha-shimoto, J. Hasegawa, T. Katoh, T. Kajimoto, M. Shiozuka, R. Matsuda, M. Node, Y. Kiso
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Journal Title
J. Chem. Soc., Chem. Commun 2008
Pages: 2379-2381
Related Report
Peer Reviewed
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