Fmoc-Asn(Glc-α-Glc)-OH | 136031-21-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Fmoc-Asn(Glc-α-Glc)-OH
• 英文别名: Fmoc-Asn(Glc2)OH
• CAS: 136031-21-5
• 化学式: C₃₁H₃₈N₂O₁₅
• 分子量: 678.647
• InChiKey: FIBQIVOEBGBQLD-XLSKMWQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.89
• 重原子数：
  48.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  274.03
• 氢给体数：
  10.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Fmoc-Asn(Glc-α-Glc)-OH 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 N^β-maltobiosyl-L-asparagine
  参考文献：
  名称：

  Synthesis and conformational analysis of N-glycopeptides that contain extended sugar chains

  摘要：

  Maltooligosaccharides with 2-7 sugar moieties were converted into beta-1-amino-1-deoxy derivatives and were coupled to N-alpha-fluorenylmethoxycarbonyl-L-aspartic acid alpha-tert-butyl beta-pentafluorophenyl ester. After trifluoroacetic acid deprotection, the resulting glycosylated asparagines were used as building blocks for the solid-phase synthesis of T-cell epitopic glycopeptide analogues. The coupling efficiencies of the glycoamino acid synthons and the acid and base stability of the resulting glycopeptides indicate the applicability of this solid-phase synthetic protocol for the incorporation of sugars that are comparable in size with that of the natural carbohydrate antennae of N-glycoproteins. The sugars placed into N-terminal position did not affect the strong alpha-helical structure of the peptides, but inhibited the disulfide-bridge formation of proximal cysteine residues in a carbohydrate length-dependent manner.

  DOI：

  10.1016/s0040-4020(01)86956-8
• 作为产物：
  描述：

  芴甲氧羰基-L-天冬氨酸-1-叔丁酯 在 三氟乙酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.83h， 生成 Fmoc-Asn(Glc-α-Glc)-OH
  参考文献：
  名称：

  Synthesis and conformational analysis of N-glycopeptides that contain extended sugar chains

  摘要：

  Maltooligosaccharides with 2-7 sugar moieties were converted into beta-1-amino-1-deoxy derivatives and were coupled to N-alpha-fluorenylmethoxycarbonyl-L-aspartic acid alpha-tert-butyl beta-pentafluorophenyl ester. After trifluoroacetic acid deprotection, the resulting glycosylated asparagines were used as building blocks for the solid-phase synthesis of T-cell epitopic glycopeptide analogues. The coupling efficiencies of the glycoamino acid synthons and the acid and base stability of the resulting glycopeptides indicate the applicability of this solid-phase synthetic protocol for the incorporation of sugars that are comparable in size with that of the natural carbohydrate antennae of N-glycoproteins. The sugars placed into N-terminal position did not affect the strong alpha-helical structure of the peptides, but inhibited the disulfide-bridge formation of proximal cysteine residues in a carbohydrate length-dependent manner.

  DOI：

  10.1016/s0040-4020(01)86956-8

文献信息

• Solid-phase synthesis of glycopeptides: synthesis of Nα-Flourenylmethoxycarbonyl L-asparagine Nβ-glycosides
  作者：Laszlo Urge、Emma Kollat、Miklos Hollosi、Ilona Laczko、Krzysztof Wroblewski、Jan Thurin、Laszlo Otvos

  DOI：10.1016/0040-4039(91)80802-d

  日期：1991.7

  It was found that crude 1-glycosylamines, prepared with saturated aqueous NH4HCO3 from reducing sugars, can be coupled with Fmoc-Asp(OPfp)-O(t)Bu in N,N-dimethylformamide-water mixtures. Purification and removal of the (t)Bu group results in N-beta-glycosides of Fmoc-Asn-OH which can be used for the solid phase synthesis of glycopeptides.