Methyl 3,6-di-O-(2-deoxy-2-valeramido-β-D-glucopyranosyloxyethyl)-α-D-mannopyranoside | 146671-96-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 3,6-di-O-(2-deoxy-2-valeramido-β-D-glucopyranosyloxyethyl)-α-D-mannopyranoside
• CAS: 146671-96-7
• 化学式: C₃₃H₆₀N₂O₁₈
• 分子量: 772.842
• InChiKey: PBRIBKNLJHDVNR-KBYUMDHZSA-N

物化性质

• 沸点：
  1051.4±65.0 °C(predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.26
• 重原子数：
  53.0
• 可旋转键数：
  22.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  293.88
• 氢给体数：
  10.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  uridine 5'-diphospho-β-D-galactose 、 Methyl 3,6-di-O-(2-deoxy-2-valeramido-β-D-glucopyranosyloxyethyl)-α-D-mannopyranoside 在 bovine (1->4)-β-D-galactosyltransferase Tris-HCl buffer 、 sodium chloride 、 manganese(ll) chloride 、 Triton X-100 作用下， 以 水 为溶剂， 生成 、 、
  参考文献：
  名称：

  Spacer-modified trisaccharide glycosides that mimic the biantennary Asn-linked oligosaccharide acceptor of (1 → 4)-β-d-galactosyltransferase and can be used as competitive inhibitors and for irreversible deactivation

  摘要：

  The biantennary spacer-modified trisaccharide glycoside methyl 3,6-di-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyloxyethyl)-alpha-D-mannopyranoside (5) was synthesised and used together with several 2-acylamino-2-deoxy-D-glucose derivatives in competition experiments with beta-D-galactosyltransferase. CoMpound 5 was an acceptor substrate (K(M) 0.18 mM) comparable to the biantennary core heptasaccharide of glycoproteins (K(M) 0.13 mM). Replacing the N-acetyl group by other N-acyl groups did not alter the kinetic parameters significantly. When the N-acyl group was iodoacetyl, the compound was an irreversible inhibitor,

  DOI：

  10.1016/s0008-6215(00)90926-1
• 作为产物：
  描述：

  Methyl 2,4-di-O-acetyl-3,6-di-O-hydroxyethyl-α-D-mannopyranoside 在 吡啶 、 2,4,6-三甲基吡啶 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 正丁胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 9.0h， 生成 Methyl 3,6-di-O-(2-deoxy-2-valeramido-β-D-glucopyranosyloxyethyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Spacer-modified trisaccharide glycosides that mimic the biantennary Asn-linked oligosaccharide acceptor of (1 → 4)-β-d-galactosyltransferase and can be used as competitive inhibitors and for irreversible deactivation

  摘要：

  The biantennary spacer-modified trisaccharide glycoside methyl 3,6-di-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyloxyethyl)-alpha-D-mannopyranoside (5) was synthesised and used together with several 2-acylamino-2-deoxy-D-glucose derivatives in competition experiments with beta-D-galactosyltransferase. CoMpound 5 was an acceptor substrate (K(M) 0.18 mM) comparable to the biantennary core heptasaccharide of glycoproteins (K(M) 0.13 mM). Replacing the N-acetyl group by other N-acyl groups did not alter the kinetic parameters significantly. When the N-acyl group was iodoacetyl, the compound was an irreversible inhibitor,

  DOI：

  10.1016/s0008-6215(00)90926-1