Fmoc-Asn(Glc-β-Glc)-OH | 135962-95-7

• 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-β-Glc)-OH
• 英文别名: (2S)-4-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid
• CAS: 135962-95-7
• 化学式: C₃₁H₃₈N₂O₁₅
• 分子量: 678.647
• InChiKey: FIBQIVOEBGBQLD-DGCQLYBQSA-N

物化性质

• 熔点：
  180-182 °C
• 沸点：
  1055.1±65.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  274
• 氢给体数：
  10
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Fmoc-L-苯丙氨酸 、 Fmoc-Asn(Glc-β-Glc)-OH 、 Fmoc-O-三苯甲基-L-丝氨酸 生成 、
  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-β-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

文献信息

• An Efficient Synthetic Route to Glycoamino Acid Building Blocks for Glycopeptide Synthesis
  作者：Mallesham Bejugam、Sabine L. Flitsch

  DOI：10.1021/ol048342n

  日期：2004.10.1

  requires access to gram quantities of glycosylated amino acid building blocks. Hence, the efficiency of synthesis of such building blocks is of great importance. Here, we report a fast and highly efficient synthetic route to Fmoc-protected asparaginyl glycosides from unprotected sugars in three steps with high yields. The glycosylated amino acids were successfully incorporated into target glycopeptides

  [反应：见正文]化学糖肽合成需要获得克量的糖基化氨基酸构件。因此，这种结构单元的合成效率非常重要。在这里，我们报告了一种快速高效的合成路线，可分三步以高收率从未保护的糖中合成Fmoc保护的天冬酰胺基糖苷。通过标准的Fmoc固相肽合成，将糖基化的氨基酸成功地掺入靶糖肽7和8中。