Nα-<2-Acrylamidoethyl 3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-glucopyranosiduronoyl>-Nε-(tert-butyloxycarbonyl)-L-lysine tert-butyl ester | 141520-92-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Nα-<2-Acrylamidoethyl 3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-glucopyranosiduronoyl>-Nε-(tert-butyloxycarbonyl)-L-lysine tert-butyl ester
• 英文别名: N^α-<2-Acrylamidoethyl 3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-glucopyranosiduronoyl>-N^ε-(tert-butyloxycarbonyl)-L-lysine tert-butyl ester；N^α-[2-Acrylamidoethyl 3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-glucopyranosiduronoyl]-N^ε-(tert-butyloxycarbonyl)-L-lysine tert-butyl ester
• CAS: 141520-92-5
• 化学式: C₃₄H₅₈N₄O₁₆
• 分子量: 778.852
• InChiKey: DVYKPRARZTVUKE-YOOYGKELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  54.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  290.0
• 氢给体数：
  9.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  Nα-<2-Acrylamidoethyl 3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-glucopyranosiduronoyl>-Nε-(tert-butyloxycarbonyl)-L-lysine tert-butyl ester 、 三氟乙酸 反应 0.75h， 以97%的产率得到N^α-<2-Acrylamidoethyl 3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-glucopyranosiduronoyl>-L-lysine (trifluoroacetate)
  参考文献：
  名称：

  Synthesis of lysine-containing fragments of the Proteus mirabilis O27 O-specific polysaccharide and neoglyco- conjugates therefrom

  摘要：

  Amide-linked lysine mono- and di-uronic acid fragments of the O-specific polysaccharide from P. mirabilis O27 have been synthesised. N(epsilon)-Boc-L-lysine tert-butyl ester was condensed with 2-azidoethyl glycosides of glucuronic acid and beta-D-GlcpNAc-(1 --> 3)-beta-D-GlcpA. Transformation of the products into 2-acrylamidoethyl glycosides, followed by deprotection using trifluoroacetic acid, gave the target monomers that were converted into high-molecular-weight copolymer-type neoglycoconjugates.

  DOI：

  10.1016/s0008-6215(00)90501-9
• 作为产物：
  描述：

  N^α-<2-Azidoethyl 3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-glucopyranosiduronoyl>-N^ε-(tert-butyloxycarbonyl)-L-lysine tert-butyl ester 在 palladium on activated charcoal 2,6-二叔丁基-4-甲基苯酚 、 Dowex 1-X₈ (hco3^-) resin 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 21.5h， 生成 Nα-<2-Acrylamidoethyl 3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-glucopyranosiduronoyl>-Nε-(tert-butyloxycarbonyl)-L-lysine tert-butyl ester
  参考文献：
  名称：

  Synthesis of lysine-containing fragments of the Proteus mirabilis O27 O-specific polysaccharide and neoglyco- conjugates therefrom

  摘要：

  Amide-linked lysine mono- and di-uronic acid fragments of the O-specific polysaccharide from P. mirabilis O27 have been synthesised. N(epsilon)-Boc-L-lysine tert-butyl ester was condensed with 2-azidoethyl glycosides of glucuronic acid and beta-D-GlcpNAc-(1 --> 3)-beta-D-GlcpA. Transformation of the products into 2-acrylamidoethyl glycosides, followed by deprotection using trifluoroacetic acid, gave the target monomers that were converted into high-molecular-weight copolymer-type neoglycoconjugates.

  DOI：

  10.1016/s0008-6215(00)90501-9