苄基2-O-[2-(乙酰氨基)-2-脱氧-beta-D-吡喃葡萄糖基]-alpha-D-吡喃甘露糖苷 | 436853-00-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 苄基2-O-[2-(乙酰氨基)-2-脱氧-beta-D-吡喃葡萄糖基]-alpha-D-吡喃甘露糖苷
• 中文别名: 苄基2-O-[2-（乙酰氨基）-2-脱氧-β-D-吡喃葡萄糖基]-α-D-甘露吡喃糖苷
• 英文名称: Benzyl 2-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-alpha-D-mannopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylmethoxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 436853-00-8
• 化学式: C₂₁H₃₁NO₁₁
• 分子量: 473.477
• InChiKey: DMMHDVIDPISODO-DUDXSYDCSA-N

物化性质

• 沸点：
  802.9±65.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  187
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 、 尿苷5'-(2-乙酰氨基-2-脱氧-ALPHA-D-葡糖基焦磷酸酯) 在 D-GlcNAc 、 recombinant human protein O-linked mannose β1,2-N-acetylgucosaminyltransferase 1 (Ser66-Thr660) 、 AMP 、 manganese(ll) chloride 作用下， 以 甘油 为溶剂， 反应 1.0h， 生成 苄基2-O-[2-(乙酰氨基)-2-脱氧-beta-D-吡喃葡萄糖基]-alpha-D-吡喃甘露糖苷
  参考文献：
  名称：

  Effects of length and amino acid sequence of O-mannosyl peptides on substrate specificity of protein O-linked mannose β1,2-N-acetylglucosaminyltransferase 1 (POMGnT1)

  摘要：

  Protein O-linked mannose beta 1,2-N-acetylglucosaminyltransferase 1 (POMGnT1) catalyzes the transfer of G1cNAc to O-mannose of glycoproteins. Mutations in the POMGnT1 gene cause muscle-eye-brain disease (MEB). POMGnT1 is a typical type 11 membrane protein, which is localized in the Golgi apparatus. However, details of the catalytic and reaction mechanism of POMGnT1 are not understood. To develop a better understanding of POMGnT1, we examined the substrate specificity of POMGnT1 using a series of synthetic O-mannosyl peptides based on the human alpha-dystroglycan (alpha-DG) sequence as substrates. O-Mannosyl peptides consisting of three to 20 amino acids are recognized as substrates. Enzyme kinetics improved with increasing peptide length up to a length of 8 amino acids but the kinetics of peptides longer than 8 amino acids were similar to those of octapeptides. Our results also show that the amino acid sequence affects POMGnT1 activity. These data suggest that both length and amino acid sequence of mannosyl peptides are determinants of POMGnT1 substrate specificity. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bbrc.2011.06.042

文献信息

• Effects of length and amino acid sequence of O-mannosyl peptides on substrate specificity of protein O-linked mannose β1,2-N-acetylglucosaminyltransferase 1 (POMGnT1)
  作者：Keiko Akasaka-Manya、Hiroshi Manya、Mamoru Mizuno、Toshiyuki Inazu、Tamao Endo

  DOI：10.1016/j.bbrc.2011.06.042

  日期：2011.7

  Protein O-linked mannose beta 1,2-N-acetylglucosaminyltransferase 1 (POMGnT1) catalyzes the transfer of G1cNAc to O-mannose of glycoproteins. Mutations in the POMGnT1 gene cause muscle-eye-brain disease (MEB). POMGnT1 is a typical type 11 membrane protein, which is localized in the Golgi apparatus. However, details of the catalytic and reaction mechanism of POMGnT1 are not understood. To develop a better understanding of POMGnT1, we examined the substrate specificity of POMGnT1 using a series of synthetic O-mannosyl peptides based on the human alpha-dystroglycan (alpha-DG) sequence as substrates. O-Mannosyl peptides consisting of three to 20 amino acids are recognized as substrates. Enzyme kinetics improved with increasing peptide length up to a length of 8 amino acids but the kinetics of peptides longer than 8 amino acids were similar to those of octapeptides. Our results also show that the amino acid sequence affects POMGnT1 activity. These data suggest that both length and amino acid sequence of mannosyl peptides are determinants of POMGnT1 substrate specificity. (C) 2011 Elsevier Inc. All rights reserved.