N^α-(fluoren-9-ylmethoxycarbonyl)-O-(β-D-glucopyranosyl)-L-serine | 149704-78-9

• 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: N^α-(fluoren-9-ylmethoxycarbonyl)-O-(β-D-glucopyranosyl)-L-serine
• 英文别名: N-(9-fluorenylmethoxycarbonyl)-O-(β-D-glucopyranosyl)-L-serine；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropanoic acid
• CAS: 149704-78-9
• 化学式: C₂₄H₂₇NO₁₀
• 分子量: 489.479
• InChiKey: DVPDMCGZSFOYKN-LLPMHQGWSA-N

物化性质

• 沸点：
  797.4±60.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  175
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N^α-(fluoren-9-ylmethoxycarbonyl)-O-(β-D-glucopyranosyl)-L-serine 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 51, Cys⁵⁶-O-(β-D-glucopyranosyl)-Ser⁵³>HBX-IX (51-56)
  参考文献：
  名称：

  Reimer, Kerry B.; Meldal, Morten; Kusumoto, Shoichi, Journal of the Chemical Society. Perkin transactions I, 1993, # 8, p. 925 - 932

  摘要：

  DOI：
• 作为产物：
  描述：

  葡萄糖丝氨酸 在 sodium methylate 、 sodium carbonate 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 3.0h， 生成 N^α-(fluoren-9-ylmethoxycarbonyl)-O-(β-D-glucopyranosyl)-L-serine
  参考文献：
  名称：

  Application of Fmoc-amino acid carrying an unmasked carbohydrate to the synthesis of the epidermal growth factor-like domain of bovine blood coagulation factor IXElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/ob/b3/b312413d/

  摘要：

  使用 9-芴甲氧羰基（Fmoc）氨基酸，通过固相法合成了在 Ser53 处携带葡萄糖的牛血凝因子 IX（45-87）的表皮生长因子（EGF）样结构域。丝氨酸 53 的导入是通过 Fmoc-丝氨酸的苯并三唑酯进行的，该酯携带一个未掩蔽的葡萄糖。其余序列也是用苯并三唑酯导入的。对粗肽的 HPLC 分析表明，葡萄糖游离羟基的酰化作用并不明显，这表明携带未掩蔽碳水化合物的氨基酸是固相合成的有用构件。

  DOI：

  10.1039/b312413d

文献信息

• Structural Requirements for CNS Active Opioid Glycopeptides
  作者：Mark Lefever、Yingxue Li、Bobbi Anglin、Dhanasekaran Muthu、Denise Giuvelis、John J. Lowery、Brian I. Knapp、Jean M. Bidlack、Edward J. Bilsky、Robin Polt

  DOI：10.1021/acs.jmedchem.5b00014

  日期：2015.8.13

  Glycopeptides related to fl-endorphin penetrate the blood brain barrier (BBB) of mice to produce antinociception. Two series of glycopeptides were assessed for opioid receptor binding affinity. Attempts to alter the mu-selectivity of [DA1a2,N-MePhe4,Gly-ol5]enkephalin (DAIVIG0)-related glycopeptides by altering the charged residues of the amphipathic helical address were unsuccessful. A series of panagonists was evaluated for antinociceptive activity (55 degrees C tail flick) in mice. A flexible linker was required to maintain antinociceptive activity. Circular dichroism (CD) in H2O, trifluoroethanol (TFE), and SDS micelles confirmed the importance of the amphipathic helices (11s -> 11sG -> 11) for antinociception. The glycosylated analogues showed only nascent helices and random coil conformations in H20. Chemical shift indices (CSI) and nuclear Overhauser effects (NOE) with 600 MHz NMR and CD confirmed helical structures in micelles, which were rationalized by molecular dynamics calculations. Antinociceptive studies with mice confirm that these glycosylated endorphin analogues are potential drug candidates that penetrate the BBB to produce potent central effects.
• Reimer, Kerry B.; Meldal, Morten; Kusumoto, Shoichi, Journal of the Chemical Society. Perkin transactions I, 1993, # 8, p. 925 - 932
  作者：Reimer, Kerry B.、Meldal, Morten、Kusumoto, Shoichi、Fukase, Koichi、Bock, Klaus

  DOI：——

  日期：——
• Application of Fmoc-amino acid carrying an unmasked carbohydrate to the synthesis of the epidermal growth factor-like domain of bovine blood coagulation factor IXElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/ob/b3/b312413d/
  作者：Toshio Takemura、Hironobu Hojo、Yoshiaki Nakahara、Takeshi Ishimizu、Sumihiro Hase

  DOI：10.1039/b312413d

  日期：——

  The epidermal growth factor (EGF)-like domain of the bovine blood coagulation factor IX (45–87) carrying glucose at Ser53 was synthesized by a solid-phase method using 9-fluorenylmethoxycarbonyl (Fmoc)-amino acids. The introduction of Ser53 was carried out using the benzotriazolyl ester of Fmoc-serine carrying an unmasked glucose. The remaining sequence was also introduced using the benzotriazolyl ester. HPLC analysis of the crude peptide shows that acylation of the free hydroxyl group of the glucose was not significant, demonstrating that the amino acid carrying an unmasked carbohydrate is a useful building block for solid-phase synthesis.

  使用 9-芴甲氧羰基（Fmoc）氨基酸，通过固相法合成了在 Ser53 处携带葡萄糖的牛血凝因子 IX（45-87）的表皮生长因子（EGF）样结构域。丝氨酸 53 的导入是通过 Fmoc-丝氨酸的苯并三唑酯进行的，该酯携带一个未掩蔽的葡萄糖。其余序列也是用苯并三唑酯导入的。对粗肽的 HPLC 分析表明，葡萄糖游离羟基的酰化作用并不明显，这表明携带未掩蔽碳水化合物的氨基酸是固相合成的有用构件。