8-methoxycarbonyloctyl 3,4,6-tri-O-benzyl-2-O-(methylthio)thiocarbonyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 180336-13-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-methoxycarbonyloctyl 3,4,6-tri-O-benzyl-2-O-(methylthio)thiocarbonyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• CAS: 180336-13-4
• 化学式: C₅₄H₆₇NO₁₃S₂
• 分子量: 1002.26
• InChiKey: DYEIMVFXQNTZKU-APVUBYPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.78
• 重原子数：
  70.0
• 可旋转键数：
  25.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  147.7
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  8-methoxycarbonyloctyl 3,4,6-tri-O-benzyl-2-O-(methylthio)thiocarbonyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以75%的产率得到8-methoxycarbonyloctyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-lyxo-hexopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Recognition of β-d-Gal p-(1 → 3)-β-d-Glc pNAc-OR acceptor analogues by the Lewis α-(1 → 34)-fucosyltransferase from human milk

  摘要：

  The Lewis alpha-(1 --> 3/4)-frucosyltransferase (E.C. 2.4.1.65) transfers L-fucose from GDP-fucose to OH-4 of the Glc pNAc residue in the disaccharide beta-D-Gal p-(1 --> 3)-beta-D-Glc pNAc-OR [R = (CH2)(8)COOMe] (1) to give the Lewis-A blood group determinant beta-D-Gal p-(1 --> 3)-[alpha-L-Fuc p-(1 --> 4)]-beta-D-Glc pNAc-OR. Five deoxy analogues of 1, as well as its N-propionyl derivative, were chemically synthesized and kinetically evaluated as both substrates and inhibitors for the enzyme from human milk. The unmodified acceptor 1 had K-m = 640 mu M with V-max set arbitrarily to 100. The 6-deoxy (K-m = 400 mu M, V-max = 90) and N-propionyl compounds (K-m = 330 mu M, V-max = 170) remained excellent substrates while the 4-deoxy compound was a very weak competitive inhibitor with K-i = 9 mM. Deoxygenation of OH-2' and OH-4' (of the Gal residue) in 1 had little effect on the activity. The OH-6 group of the Gal residue proved to be critical for recognition by the enzyme since substitution of this group with hydrogen led to an inactive compound. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0008-6215(96)00047-x
• 作为产物：
  描述：

  8-methoxycarbonyloctyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 咪唑 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 8-methoxycarbonyloctyl 3,4,6-tri-O-benzyl-2-O-(methylthio)thiocarbonyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Recognition of β-d-Gal p-(1 → 3)-β-d-Glc pNAc-OR acceptor analogues by the Lewis α-(1 → 34)-fucosyltransferase from human milk

  摘要：

  The Lewis alpha-(1 --> 3/4)-frucosyltransferase (E.C. 2.4.1.65) transfers L-fucose from GDP-fucose to OH-4 of the Glc pNAc residue in the disaccharide beta-D-Gal p-(1 --> 3)-beta-D-Glc pNAc-OR [R = (CH2)(8)COOMe] (1) to give the Lewis-A blood group determinant beta-D-Gal p-(1 --> 3)-[alpha-L-Fuc p-(1 --> 4)]-beta-D-Glc pNAc-OR. Five deoxy analogues of 1, as well as its N-propionyl derivative, were chemically synthesized and kinetically evaluated as both substrates and inhibitors for the enzyme from human milk. The unmodified acceptor 1 had K-m = 640 mu M with V-max set arbitrarily to 100. The 6-deoxy (K-m = 400 mu M, V-max = 90) and N-propionyl compounds (K-m = 330 mu M, V-max = 170) remained excellent substrates while the 4-deoxy compound was a very weak competitive inhibitor with K-i = 9 mM. Deoxygenation of OH-2' and OH-4' (of the Gal residue) in 1 had little effect on the activity. The OH-6 group of the Gal residue proved to be critical for recognition by the enzyme since substitution of this group with hydrogen led to an inactive compound. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0008-6215(96)00047-x