β-D-fucosylamine | 146387-58-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-fucosylamine
• 英文别名: L-fucosylamine；β-L-Fucosylamin；(2R,3R,4S,5R,6R)-2-amino-6-methyloxane-3,4,5-triol
• CAS: 146387-58-8
• 化学式: C₆H₁₃NO₄
• 分子量: 163.174
• InChiKey: UTVXFQMLZSPQLB-FPRJBGLDSA-N

物化性质

• 沸点：
  331.5±42.0 °C(Predicted)
• 密度：
  1.406±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  95.9
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  β-D-fucosylamine 在 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 N^α-fluorenylmethoxycarbonyl-N^β-β-D-fucopyranosyl-L-aspargine
  参考文献：
  名称：

  Fmoc-protected, glycosylated asparagines potentially useful as reagents in the solid-phase synthesis of N-glycopeptides

  摘要：

  I-Amino 1-deoxy derivatives of unprotected O-beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-glucopyranose, 2-acetamido-2-deoxy-D-galactose, D-galactose, lactose, D-fucose, D-mannose, and 2-deoxy-D-arabino-hexose were prepared and acylated with N-fluorenylmethoxycarbonylaspartic acid alpha-tert-butyl ester. The anomeric configuration of the N-glycosyl bond (including that of the mannose derivative) in each of the purified compounds was shown to be beta. The probable stability of the N-glycosyl and glycosidic bonds during the conditions of solid-phase peptide synthesis was investigated by treatment of the glycosylated asparagine derivatives with different concentrations of trifluoroacetic acid. Based on their stability, we found that Fmoc-Asn(sugar)-OH derivatives are excellent candidates for automated synthesis of biologically active glycopeptides.

  DOI：

  10.1016/0008-6215(92)80080-k
• 作为产物：
  描述：

  D-Fucose 在 碳酸氢铵 作用下， 以 水 为溶剂， 反应 168.0h， 以80%的产率得到β-D-fucosylamine
  参考文献：
  名称：

  Fmoc-protected, glycosylated asparagines potentially useful as reagents in the solid-phase synthesis of N-glycopeptides

  摘要：

  I-Amino 1-deoxy derivatives of unprotected O-beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-glucopyranose, 2-acetamido-2-deoxy-D-galactose, D-galactose, lactose, D-fucose, D-mannose, and 2-deoxy-D-arabino-hexose were prepared and acylated with N-fluorenylmethoxycarbonylaspartic acid alpha-tert-butyl ester. The anomeric configuration of the N-glycosyl bond (including that of the mannose derivative) in each of the purified compounds was shown to be beta. The probable stability of the N-glycosyl and glycosidic bonds during the conditions of solid-phase peptide synthesis was investigated by treatment of the glycosylated asparagine derivatives with different concentrations of trifluoroacetic acid. Based on their stability, we found that Fmoc-Asn(sugar)-OH derivatives are excellent candidates for automated synthesis of biologically active glycopeptides.

  DOI：

  10.1016/0008-6215(92)80080-k

文献信息

• ANTIBODY-DRUG CONJUGATE (ADC) AND METHOD FOR FORMING THE SAME
  申请人：Industrial Technology Research Institute

  公开号：US20170119902A1

  公开（公告）日：2017-05-04

  An antibody-drug conjugate (ADC) of formula (I) or a pharmaceutically acceptable salt or solvate thereof is provided. In formula (I), p is an integer ranging from 1 to 26, A is an antibody, and -(L-D) is a linker-drug unit. L is a linker unit having a glycopeptide, and D is a drug unit. The antibody is conjugated to the linker unit through a cysteine residue of the antibody. A method for forming an antibody-drug conjugate (ADC) is also provided. A-(L-D) p (I)

  提供了公式（I）的抗体药物结合物（ADC）或其药学上可接受的盐或溶剂。在公式（I）中，p是1到26的整数，A是抗体，而-（L-D）是连接-药物单元。L是具有糖肽的连接单元，D是药物单元。通过抗体的半胱氨酸残基将抗体与连接单元结合。还提供了一种形成抗体药物结合物（ADC）的方法。A-（L-D）p（I）
• COMPOUNDS, LINKER-DRUGS AND LIGAND-DRUG CONJUGATES
  申请人：Industrial Technology Research Institute

  公开号：US20180016300A1

  公开（公告）日：2018-01-18

  A compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof is provided. In formula (I), R1, R2 and R3 are each, independently, hydrogen, amino, nitro, halogen, hydroxyl, C1-C6 alkoxy, carboxylic acid, C1-C6 alkoxycarbonyl, C1-C6 amino, C1-C6 aminocarbonyl, C1-C6 alkyl, branched C1-C6 alkyl, C1-C6 cycloalkyl, C1-C6 heterocyclic, aryl or heteroaryl, provided at least one of R1 and R3 is an amino group. A linker-drug and a ligand-drug conjugate including the compound are also provided.
• Fmoc-protected, glycosylated asparagines potentially useful as reagents in the solid-phase synthesis of N-glycopeptides
  作者：Laszlo Urge、Laszlo Otvos、Emma Lang、Krzysztof Wroblewski、Ilona Laczko、Miklos Hollosi

  DOI：10.1016/0008-6215(92)80080-k

  日期：1992.11

  I-Amino 1-deoxy derivatives of unprotected O-beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-glucopyranose, 2-acetamido-2-deoxy-D-galactose, D-galactose, lactose, D-fucose, D-mannose, and 2-deoxy-D-arabino-hexose were prepared and acylated with N-fluorenylmethoxycarbonylaspartic acid alpha-tert-butyl ester. The anomeric configuration of the N-glycosyl bond (including that of the mannose derivative) in each of the purified compounds was shown to be beta. The probable stability of the N-glycosyl and glycosidic bonds during the conditions of solid-phase peptide synthesis was investigated by treatment of the glycosylated asparagine derivatives with different concentrations of trifluoroacetic acid. Based on their stability, we found that Fmoc-Asn(sugar)-OH derivatives are excellent candidates for automated synthesis of biologically active glycopeptides.