CAS: 125455-64-3; N-((2R,3R,4R,5R,6R)-4-(((2R,3R,4R,5S,6R)-3-Acetamido-4,5-Dihydroxy-6-(Hydroxymethyl)Tetrahydro-2H-Pyran-2-yl)Oxy)-5-Hydroxy-6-(Hydroxymethyl)-2-(4-Nitrophenoxy)Tetrahydro-2H-Pyran-3-yl)Acetamide

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参考标题:Specificity Of β1,4-Galactosyltransferase Inhibition By 2-Naphthyl 2-Butanamido-2-Deoxy-1-Thio-β-D-Glucopyranoside
作者:Yin Gao,Carmen Lazar,Walter A. Szarek,Inka Brockhausen |发布日期:2010.10
摘要:Inhibitors Of Galactosyltransferase (Galt) Have The Potential Of Reducing The Amounts Of Adhesive Carbohydrates On Secreted And Cell Surface-Bound Glycoproteins. We Recently Found A Potent Inhibitor Of β4Galt, 2-Naphthyl 2-Butanamido-2-Deoxy-1-Thio-β-D-Glucopyranoside (Compound 612). In This Work, We Have Tested Compound 612 For The Specificity Of Its Inhibition And Examined Its Effect On Galt, And On Glcnac- And Galnac-Transferases In Homogenates Of Different Cell Lines, As Well As On Recombinant Glycosyltransferases. Compound 612 Was Found To Be A Specific Inhibitor Of β4Galt. The Specificity Of Recombinant Human β3Galt5 That Also Acts On Glcnac-R Substrates, Revealed Similarities To Bovine Milk β4Galt. However, 612 Was A Poor Substrate And Not An Inhibitor For β3Galt5. To Further Determine The Specific Structures Responsible For The Inhibitory Property Of 612, We Synthesized (2-Naphthyl)-2-Butanamido-2-Deoxy-β-D-Glucopyranosylamine (Compound 629) Containing Nitrogen In The Glycosidic Linkage, And Compared It To Other Naphthyl And Quinolinyl Derivatives Of Glcnac As Substrates And Inhibitors. Compound 629 Was A Substrate For Both β4Galt And β3Galt5. This Suggests That Properties Of 612 Other Than The Presence Of The Naphthyl Ring Alone Were Responsible For Its Inhibitory Action. The Results Suggest A Usefulness Of 612 In Specifically Blocking The Synthesis Of Type 2 Chains And Thus Epitopes Attached To Type 2 Chains. In Addition, 612 Potently Inhibits β4Galt In Cell Homogenates And Thus Allows Assaying β3Galt Activity In The Presence Of β4Galt.

合成参考文献

参考DOI号:10.1016/j.carres.2011.03.036