N-(9-fluorenylmethoxycarbonyl)-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl]-(S)-tyrosine | 935458-01-8

• 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: N-(9-fluorenylmethoxycarbonyl)-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl]-(S)-tyrosine
• 英文别名: Nα-(9-fluorenylmethoxycarbonyl)-O-[(2,3,6-tri-O-acetyl)-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl]-L-tyrosine；(2S)-3-[4-[(2S,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyphenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 935458-01-8
• 化学式: C₅₀H₅₅NO₂₂
• 分子量: 1021.98
• InChiKey: DUSUGTFSYKNLKW-FAHRHMCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  73
• 可旋转键数：
  27
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  297
• 氢给体数：
  2
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl]-(S)-tyrosine 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Site-Specific Incorporation of Glycosylated Serine and Tyrosine Derivatives into Proteins

  摘要：

  Glycosylation of proteins can have a dramatic effect on their physical, chemical, and biological properties. Analogues of dihydrofolate reductase and firefly luciferase containing glycosylated amino acids at single, predetermined sites have been elaborated. Misacylated suppressor tRNAs activated with glycosylated serine and tyrosine derivatives were used for suppression of the nonsense codons in a cell-free protein biosynthesizing system, thereby permitting the preparation of the desired glycosylated proteins. In this fashion, it was possible to obtain proteins containing both mono- and diglycosylated amino acids, including glycosylated serine and tyrosine moieties. For the modified firefly luciferases, the effect of these substitutions on the wavelength of the light emitted by firefly luciferase was investigated. The maximum wavelength for mutants containing peracetylated glycosylated serine derivatives at position 284 showed a red shift in the emission spectra. For mutants containing glycosylated tyrosines, the red shift was observed only when the carbohydrate moiety was fully deacetylated.

  DOI：

  10.1021/ja067466n
• 作为产物：
  描述：

  Fmoc-L-酪氨酸 、 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以35%的产率得到N-(9-fluorenylmethoxycarbonyl)-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl]-(S)-tyrosine
  参考文献：
  名称：

  Facile synthesis of glycosylated Fmoc amino acid building blocks assisted by microwave irradiation

  摘要：

  The synthesis of glycosylated Fmoc amino acids by reaction of mono- and disaccharide peracetates with Fmoc amino acids having free carboxyl groups was rapidly promoted by Lewis acids (SnCl4, BF3 center dot Et2O) under microwave irradiation. The products are useful building blocks for the synthesis of glycopeptides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.07.040