Fmoc-Asn(Glc)-OH | 135962-94-6

• 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: Fmoc-Asn(Glc)-OH
• 英文别名: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]butanoic acid
• CAS: 135962-94-6
• 化学式: C₂₅H₂₈N₂O₁₀
• 分子量: 516.505
• InChiKey: WTRCVJXQENBNRW-MZXGMOTRSA-N

物化性质

• 沸点：
  893.4±65.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.72
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  194.88
• 氢给体数：
  7.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Fmoc-L-苯丙氨酸 、 Fmoc-Asn(Glc)-OH 、 Fmoc-O-三苯甲基-L-丝氨酸 生成 (S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-propionylamino]-3-phenyl-propionic acid 、 (S)-2-{(S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-propionylamino]-3-phenyl-propionylamino}-3-hydroxy-propionic acid
  参考文献：
  名称：

  Synthesis of N-linked glycopeptides on solid support and their evaluation as protease substrates

  摘要：

  A range of glycopeptides containing protease cleavage sites were synthesized on solid support using, Fmoc-based solid phase glycopeptide synthesis. The immobilized peptides were studied as substrates for the proteases chymotrypsin and thermolysin. For chymotrypsin, N-glycosylation of an Asn residue at the P-2 site appears to reduce hydrolysis whereas glycosylation of the P-2, site does not appear to affect peptide hydrolysis by thermolysin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.031
• 作为产物：
  描述：

  Nα-fluorenylmethoxycarbonyl-L-aspartic acid α-tert-butyl-β-pentafluorophenyl ester 在 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 Fmoc-Asn(Glc)-OH
  参考文献：
  名称：

  Solid-phase synthesis of glycopeptides: synthesis of Nα-Flourenylmethoxycarbonyl L-asparagine Nβ-glycosides

  摘要：

  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.

  DOI：

  10.1016/0040-4039(91)80802-d