2010 Fiscal Year Final Research Report
Development of Novel Glycosylation Reaction Using Odorless Benzenethiols
| Project/Area Number |
20590022
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | Suzuka University of Medical Science |
|---|
Principal Investigator |
KAJIMOTO Tetsuya Suzuka University of Medical Science, 薬学部, 教授(特任) (80185777)
|
|---|
| Project Period (FY) |
2008 – 2010
|
| 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 |
|---|
| 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.
|
Research Products
(15 results)
-
[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
-
Journal Title
Bioorg.Med.Chem. (in press)
-
-
-
-
-
-
-
-
-
-
-
-
-
-
[Remarks] ホームページ等
