4-methylumbelliferyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-methylumbelliferyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside
• 英文别名: 4-methylumbelliferyl 2-acetamido-2-deoxy-3-(β-D-galactopyranosyl)-α-D-galactopyranoside；4-methylumbelliferyl α-T-antigen；Galβ1-3GalNAc-α-(4-MU)；4(MU) α-T-antigen；4-MU α-T-antigen；4-Methylumbelliferyl 2-acetamido-3-O-(b-D-galactopyranosyl)-a-D-galactopyranoside；N-[(2R,3R,4R,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-(4-methyl-2-oxochromen-7-yl)oxy-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• 化学式: C₂₄H₃₁NO₁₃
• 分子量: 541.509
• InChiKey: VSWQTQWBDDXHMJ-IJHJDGDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  214
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  4-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以100%的产率得到4-methylumbelliferyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Di-tert-butylsilylene-Directed α-Selective Synthesis of 4-Methylumbelliferyl T-Antigen

  摘要：

  We have succeeded in the facile synthesis of 4-methylumbelliferyl T-antigen as a substrate for endo-alpha-N-acetylgalactosaminidase by exploiting the combination of the di-tert-butylsilylene effect and the Mitsunobu reaction.

  DOI：

  10.1021/ol051592z

文献信息

• A novel fluorescent assay for T-synthase activity
  作者：T. Ju、B. Xia、R. P. Aryal、W. Wang、Y. Wang、X. Ding、R. Mi、M. He、R. D. Cummings

  DOI：10.1093/glycob/cwq168

  日期：2011.3.1

  Loss of T-synthase (uridine diphosphate galactose:N-acetylgalactosaminyl-α1-Ser/Thr β3galactosyltransferase), a key enzyme required for the formation of mucin-type core 1 O-glycans, is observed in several human diseases, including cancer, Tn syndrome and IgA nephropathy, but current methods to assay the enzyme use radioactive substrates and complicated isolation of the product. Here we report the development of a novel fluorescent assay to measure its activity in a variety of tumor cell lines. Deficiencies in T-synthase activity correlate with mutations in the gene encoding the molecular chaperone Cosmc that is required for folding the T-synthase. This new high-throughput assay allows for facile screening of tumor specimens and other biological material for T-synthase activity and could be used diagnostically.

  T-合成酶（尿苷二磷酸半乳糖: N-乙酰半乳糖胺基-α1-丝氨酸/苏氨酸 β3-半乳糖转移酶）是形成粘蛋白类型核心1 O-糖苷的关键酶，在多种人类疾病中被观察到其缺失，包括癌症、Tn综合症和IgA肾病，但目前检测该酶的方法使用放射性底物并需要复杂的产物分离。在此，我们报告了一种新型荧光检测方法，可以在多种肿瘤细胞系中测量其活性。T-合成酶活性的缺乏与编码分子伴侣Cosmc的基因突变相关，Cosmc对于T-合成酶的折叠至关重要。这种新的高通量检测方法能够方便地筛选肿瘤标本和其他生物材料中的T-合成酶活性，并可用于诊断。
• A straightforward α-selective aromatic glycosylation and its application for stereospecific synthesis of 4-methylumbelliferyl α-T-antigen
  作者：Shih-Sheng Chang、Chun-Cheng Lin、Yaw-Kuen Li、Kwok-Kong Tony Mong

  DOI：10.1016/j.carres.2008.12.013

  日期：2009.3

  A practical and efficient alpha-selective aromatic glycosylation with simple per-O-acetyl glycopyranosyl trichloroacetimidates is reported. The method is particularly effective for L-fucosyl and 2-azido-2-deoxy-D-galatosaminyl imidates, with which exclusive alpha-selectivity was achieved. The synthetic utility of this method was demonstrated in the stereoselective synthesis of 4-methylumbelliferyl alpha-T-antigen. (C) 2008 Elsevier Ltd. All rights reserved.
• Di-<i>tert</i>-butylsilylene-Directed α-Selective Synthesis of 4-Methylumbelliferyl T-Antigen
  作者：Akihiro Imamura、Hiromune Ando、Hideharu Ishida、Makoto Kiso

  DOI：10.1021/ol051592z

  日期：2005.9.1

  We have succeeded in the facile synthesis of 4-methylumbelliferyl T-antigen as a substrate for endo-alpha-N-acetylgalactosaminidase by exploiting the combination of the di-tert-butylsilylene effect and the Mitsunobu reaction.