(2S,3R,4E)-2-(4-carboxymethyl-2-nitrobenzyloxycarbonylamino)-1-[4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxy]-3-hydroxy-4-octadecene | 132363-81-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4E)-2-(4-carboxymethyl-2-nitrobenzyloxycarbonylamino)-1-[4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxy]-3-hydroxy-4-octadecene
• CAS: 132363-81-6
• 化学式: C₄₀H₆₄N₂O₁₈
• 分子量: 860.951
• InChiKey: GWXWDIHGXOXPQV-JWELAYIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  60.0
• 可旋转键数：
  26.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  306.53
• 氢给体数：
  9.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  胞苷-5'-单磷酸-N-乙酰神经氨酸 、 (2S,3R,4E)-2-(4-carboxymethyl-2-nitrobenzyloxycarbonylamino)-1-[4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxy]-3-hydroxy-4-octadecene 在 calf intestinal alkaline phosphatase 、 Galβ-1,4GlcNAcα-2,3-(N)-sialyltransferase 、 sodium cacodylate 、 Triton X-100 、 α-lactalbumin 作用下， 反应 72.0h， 以67.1%的产率得到(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2-3)-β-D-galactopyranosyl-(1-4)-β-D-glucopyranosyloxy-(1-1)-(2S,3R,4E)-2-(4-carboxymethyl-2-nitrobenzyloxycarbonylamino)-3-hydroxy-4-octadecene
  参考文献：
  名称：

  Chemoenzymic synthesis of potentially caged glycoshingolipids (GSLs): potentially caged lyso-GM3 and its analogue

  摘要：

  In a previous work, a number of potentially caged sphingolipids and glycosphingolipids were chemically synthesized (Zehavi, 1997. Chem. Phys. Lipids 90, 55-61). The effects of G(M3) and to a lesser extent, of lyso-G(M3), are being studied. Considering that biologically inert, caged lyso-G(M3) could be photolysed in the cell to release lyso-G(M3), thus creating an attractive opportunity to study the subsequent sequence of events in the cell, the chemoenzymic synthesis of the potentially caged lyso-G(M3), (5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid)-(2-3)-beta-D-galactopyranosyl-(1-4)-beta-D-glucopyranosyloxy(1-1)-(2S,3R,4E)-2-(4-carboxymethyl-2-nitrobenzyloxycarbonyl- amino)-3-hydroxy-4-octadecene and of a potentially caged G(M3) analogue, (5-acetamido-3,5-dideoxy-D- glycero-alpha-D-galacto-2-nonulopyranosylonic acid)-(2-3)-beta-D-galactopyranosyl-(1-4)-beta-D-glucopyranosyloxy-(1-3)-(2S, 3R, 4E)-2-(4-carboxymethyl-2-nitro-benzyloxycarbonylamino) -1-hydroxy-4-octadecene was undertaken. Both compounds, being 2-nitrobezyloxycarbonyl derivatives, are light-sensitive and could be efficiently photolysed to the biologically active, corresponding lyso-GSLs. (C) 1998 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(98)00008-5
• 作为产物：
  描述：

  (2S,3R,4E)-2-(4-carboxymethyl-2-nitrobenzyloxycarbonylamino)-3-hydroxy-1-[4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy]-4-octadecene 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以96%的产率得到(2S,3R,4E)-2-(4-carboxymethyl-2-nitrobenzyloxycarbonylamino)-1-[4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxy]-3-hydroxy-4-octadecene
  参考文献：
  名称：

  Chemoenzymic synthesis of potentially caged glycoshingolipids (GSLs): potentially caged lyso-GM3 and its analogue

  摘要：

  In a previous work, a number of potentially caged sphingolipids and glycosphingolipids were chemically synthesized (Zehavi, 1997. Chem. Phys. Lipids 90, 55-61). The effects of G(M3) and to a lesser extent, of lyso-G(M3), are being studied. Considering that biologically inert, caged lyso-G(M3) could be photolysed in the cell to release lyso-G(M3), thus creating an attractive opportunity to study the subsequent sequence of events in the cell, the chemoenzymic synthesis of the potentially caged lyso-G(M3), (5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid)-(2-3)-beta-D-galactopyranosyl-(1-4)-beta-D-glucopyranosyloxy(1-1)-(2S,3R,4E)-2-(4-carboxymethyl-2-nitrobenzyloxycarbonyl- amino)-3-hydroxy-4-octadecene and of a potentially caged G(M3) analogue, (5-acetamido-3,5-dideoxy-D- glycero-alpha-D-galacto-2-nonulopyranosylonic acid)-(2-3)-beta-D-galactopyranosyl-(1-4)-beta-D-glucopyranosyloxy-(1-3)-(2S, 3R, 4E)-2-(4-carboxymethyl-2-nitro-benzyloxycarbonylamino) -1-hydroxy-4-octadecene was undertaken. Both compounds, being 2-nitrobezyloxycarbonyl derivatives, are light-sensitive and could be efficiently photolysed to the biologically active, corresponding lyso-GSLs. (C) 1998 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(98)00008-5