(2S,3R,4E)-2-(4-carboxymethyl-2-nitrobenzyloxycarbonylamino)-1-hydroxy-3-[4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy]-4-octadecene | 212124-65-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3R,4E)-2-(4-carboxymethyl-2-nitrobenzyloxycarbonylamino)-1-hydroxy-3-[4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy]-4-octadecene
• CAS: 212124-65-7
• 化学式: C₅₄H₇₈N₂O₂₅
• 分子量: 1155.21
• InChiKey: VXCVYAWOULSVEI-FFKLRAPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  81.0
• 可旋转键数：
  33.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  349.02
• 氢给体数：
  2.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-2-(4-carboxymethyl-2-nitrobenzyloxycarbonylamino)-1-hydroxy-3-[4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy]-4-octadecene 在 calf intestinal alkaline phosphatase 、 甲醇 、 Galβ-1,4GlcNAcα-2,3-(N)-sialyltransferase 、 sodium methylate 、 sodium cacodylate 、 Triton X-100 、 α-lactalbumin 作用下， 以 二氯甲烷 为溶剂， 反应 72.42h， 生成 (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2-3)-β-D-galactopyranosyl-(1-4)-β-D-glucopyranosyloxy-(1-3)-(2S,3R,4E)-2-(4-carboxymethyl-2-nitrobenzyloxycarbonylamino)-1-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：

  2,2',3,3',4',6,6'-七-O-乙酰基-alpha-D-乳糖基溴化物 、 (2S,3R,4E)-2-(4-carboxymethyl-2-nitrobenzyloxycarbonylamino)-1,3-dihydroxy-octadecene 在 氰化汞 作用下， 以 硝基甲烷 、 苯 为溶剂， 以4%的产率得到(2S,3R,4E)-2-(4-carboxymethyl-2-nitrobenzyloxycarbonylamino)-1-hydroxy-3-[4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy]-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