ArticleBioorganic & medicinal chemistry2010
Synthesis of C-glycoside analogues of beta-galactosamine-(1-->4)-3-O-methyl-D-chiro-inositol and assay as activator of protein phosphatases PDHP and PP2Calpha.
Article in Bioorganic & medicinal chemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 17 citations in OpenAlex.
- Design and synthesis of conformationally constrained Tn antigen mimics.Tetrahedron letters · 2026Article
- Synthesis ofTetrahedron letters · 2021Article
- D-chiro-inositol glycan stimulates insulin secretion in pancreatic β cells.Molecular and cellular endocrinology · 2014Article
- The phosphatase Ptc7 induces coenzyme Q biosynthesis by activating the hydroxylase Coq7 in yeast.The Journal of biological chemistry · 2013Article
- Synthesis of the C-glycoside of α-(D)-mannose-(1 → 6)-(D)-myo-inositol.Organic & biomolecular chemistry · 2013Article
- Inositol, glycogen, insulin, and six nobelists.The Journal of biological chemistry · 2013Article
- D-chiro-inositol glycans in insulin signaling and insulin resistance.Molecular medicine (Cambridge, Mass.)Review
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Authors and funding
10 authors at 6 institutions in 2 countries.
Funding
Abstract
The glycan beta-galactosamine-(1-4)-3-O-methyl-D-chiro-inositol, called INS-2, was previously isolated from liver as a putative second messenger-modulator for insulin. Synthetic INS-2 injected intravenously in rats is both insulin-mimetic and insulin-sensitizing. This bioactivity is attributed to allosteric activation of pyruvate dehydrogenase phosphatase (PDHP) and protein phosphatase 2Calpha (PP2Calpha). Towards identification of potentially metabolically stable analogues of INS-2 and illumination of the mechanism of enzymatic activation, C-INS-2, the exact C-glycoside of INS-2, and C-INS-2-OH the deaminated analog of C-INS-2, were synthesized and their activity against these two enzymes evaluated. C-INS-2 activates PDHP comparable to INS-2, but failed to activate PP2Calpha. C-INS-2-OH was inactive against both phosphatases. These results and modeling of INS-2, C-INS-2 and C-INS-2-OH into the 3D structure of PDHP and PP2Calpha, suggest that INS-2 binds to distinctive sites on the two different phosphatases to activate insulin signaling. Thus the carbon analog could selectively favor glucose disposal via oxidative pathways.
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