Nα-(2-Acrylamidoethyl β-D-glucopyranosiduronoyl)-Nε-(tert-butyloxycarbonyl)-L-lysine methyl ester | 141520-87-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Nα-(2-Acrylamidoethyl β-D-glucopyranosiduronoyl)-Nε-(tert-butyloxycarbonyl)-L-lysine methyl ester
• 英文别名: N^α-(2-Acrylamidoethyl β-D-glucopyranosiduronoyl)-N^ε-(tert-butyloxycarbonyl)-L-lysine methyl ester
• CAS: 141520-87-8
• 化学式: C₂₃H₃₉N₃O₁₁
• 分子量: 533.576
• InChiKey: KUSJEEKZORFDPH-WPAYCCBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.53
• 重原子数：
  37.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  201.98
• 氢给体数：
  6.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Nα-(2-Acrylamidoethyl β-D-glucopyranosiduronoyl)-Nε-(tert-butyloxycarbonyl)-L-lysine methyl ester 在 sodium hydroxide 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 Nα-(2-Acrylamidoethyl β-D-glucopyranosiduronoyl)-L-lysine
  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：

  S-2-(苄氧羰基氨基)-6-(叔丁氧羰基氨基)己酸甲酯 在 palladium on activated charcoal 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 49.5h， 生成 Nα-(2-Acrylamidoethyl β-D-glucopyranosiduronoyl)-Nε-(tert-butyloxycarbonyl)-L-lysine methyl 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