2007 Fiscal Year Final Research Report Summary
Development of the sugar derivatives having anti-pylori activities
| Project/Area Number |
18550160
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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 |
Chemistry related to living body
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| Research Institution | The Noguchi Institute |
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Principal Investigator |
YAMANOI Takashi The Noguchi Institute, 研究部, Chief Researcher (20182595)
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| Co-Investigator(Kenkyū-buntansha) |
FUJITA Masaya The Noguchi Institute, 研究部, Researcher (20321672)
KATSURAYA Kaname Wayo Women's University, 家政学部, Associated Professor (20251465)
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| Project Period (FY) |
2006 – 2007
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| Keywords | antiuylori agent / pylori / αGlcNAc / synthesis / N-acetyl-glucosamine / cluster / glycoside / medicine |
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| Research Abstract |
1. Synthesis of the sugar chain units of gastric mucins involving αGlcNAc residues which are expected to have an antipylori activity.
We investigated the synthesis of partial units of a gastric mucin, GlcNAcαl→4Ga1β1-6 (G1cNAcαl→4Ga1β1→4GalNAcαl→Ser (Thr) by the glycosylation method using the benzyl protected G1cNAcOAc as a donor and Yb (OTf)_3 - cat. BF3- OEt as an activating system. The glycosidation using aryl alcohols successfully afforded the aryl 0-glycosides having an αGlcNAc residue, however the reaction using typical alcohols reduced the α-stereoselectivities. The detailed glycosylation investigation revealed that the reactions using the benzylated GlcNTrocOAc as a donor produced the O-glycosides having an αGlcNAc residue even when the typical alcohols were used. The unit of trioligosaccharide, GlcNAcαl→4Ga1β1→4GalNAc was synthesized by the glycosylation method. In addition, the method was applicable to the synthesis of the derivatives of GalNAcαl→Ser (Thr) by using Ga1NTrocOAc as a donor and Yb (OTf)_3-cat. BF3・OEt as an activating system.
2. Evaluation of the antipylori activities for the synthesized compounds.
We designed and synthesized the trehalosamine derivatives (2 (H_2N)Glc-Glc (NH_2)2) as the analog of GlcNAcα1→4Gal. In vitro tests indicated that the compounds had a significantly strong antipylori activity.
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