FMOC-O-三苯甲基-D-苏氨酸 | 682800-84-6

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: FMOC-O-三苯甲基-D-苏氨酸
• 英文名称: Fmoc-D-Thr(Trt)-OH
• 英文别名: Fmoc-D-Thr(OTrt)-OH；(2R,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-trityloxybutanoic acid
• CAS: 682800-84-6
• 化学式: C₃₈H₃₃NO₅
• 分子量: 583.684
• InChiKey: JARBLLDDSTVWSM-OSPAZUARSA-N

物化性质

• 沸点：
  753.0±60.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• WGK Germany：
  2

反应信息

• 作为反应物：
  描述：

  FMOC-O-三苯甲基-D-苏氨酸 、 Fmoc-Thr-OH 在 哌啶 、 2,4,6-三甲基吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 生成 Fmoc-Thr-Pro-Gly-Hex-OH
  参考文献：
  名称：

  Divergent Behavior of Glycosylated Threonine and Serine Derivatives in Solid Phase Peptide Synthesis

  摘要：

  Solid phase peptide coupling of glycosylated threonlne derivatives was systematically evaluated. In contrast to glycosylated serine derivatives which are highly prone to epimerization, glycosylated threonine derivatives produce only negligible amounts of epimerization. Under forcing conditions, glycosylated threonine analogs undergo beta-elimination, rather than epimerization. Mechanistic studies and molecular modeling were used to understand the origin of the differences in reactivity.

  DOI：

  10.1021/ol301723e

文献信息

• Divergent Behavior of Glycosylated Threonine and Serine Derivatives in Solid Phase Peptide Synthesis
  作者：Yalong Zhang、Saddam M. Muthana、Joseph J. Barchi、Jeffrey C. Gildersleeve

  DOI：10.1021/ol301723e

  日期：2012.8.3

  Solid phase peptide coupling of glycosylated threonlne derivatives was systematically evaluated. In contrast to glycosylated serine derivatives which are highly prone to epimerization, glycosylated threonine derivatives produce only negligible amounts of epimerization. Under forcing conditions, glycosylated threonine analogs undergo beta-elimination, rather than epimerization. Mechanistic studies and molecular modeling were used to understand the origin of the differences in reactivity.