Regioselective glycosylation of fully unprotected sugars by means of molecular recognition using arylboronic acid
| Project/Area Number |
19590010
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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 | Kitasato University |
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Principal Investigator |
NISHINO Takashi Kitasato University, 薬学部, 講師 (50180625)
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| Co-Investigator(Kenkyū-buntansha) |
KAJI Eisuke 北里大学, 名誉教授 (60050598)
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| Project Period (FY) |
2007 – 2009
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| Project Status |
Completed (Fiscal Year 2009)
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| Budget Amount *help |
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2009: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2008: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2007: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
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| Keywords | 糖鎖 / アリールボロン酸 / 分子認識 / グリコシル化 / 無保護 / 位置選択性 / 合成化学 |
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| Research Abstract |
The methodology is adapted to molecular recognition of sugar structures with arylboronic acids, which from 5-membered boronates from 1,2-cis-dihydroxy groups, or 6-membered boronates from 1,3-dihydroxy groups. As expected glycosylation occurs on the left hydroxy group free from the boronate formation, and then the boronates are removed in situ by aqueous workup to yield various disaccharides in one-pot process.
Various hexoses. eg., D-glucose, D-galactose, D-mannose were glycosylated, after boronate formation, with phenyl per-O-benzoyl-1-thio-β-D-glucopyranoside, -β-D-galactopyranoside and -α-D-mannopyranoside in the presence of promoters (NIS-TMSOTf) to furnish corresponding disaccharides ; glycosyl-β(1→6)-D-glucose, -β(1→6)-D-galactose, -βα(1,1)-D-mannoside in good yields.
This method would be of significance with respect to regio- and stereoselecyive glycosylation, which might contribute to simple, one-pot preparation of various oligosaccharides of biological interest.
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Report
(4 results)
Research Products
(18 results)
