N-Alpha-t-Boc-N-beta-xanthyl-L-asparagine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-Alpha-t-Boc-N-beta-xanthyl-L-asparagine
• 英文别名: 2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-(9H-xanthen-9-ylamino)butanoic acid
• 化学式: C₂₂H₂₄N₂O₆
• 分子量: 412.442
• InChiKey: YMGDQLXBNMRJMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-Alpha-t-Boc-N-beta-xanthyl-L-asparagine 在 lithium aluminium tetrahydride 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 16.83h， 生成 tert-butyl N-[1,4-dioxo-4-(9H-xanthen-9-ylamino)butan-2-yl]carbamate
  参考文献：
  名称：

  A New Approach to Obtaining N α-t-Boc-Amino Acid Aldehydes from Asparagine and Glutamine for Reduced Amide Pseudopeptide Solid-Phase Synthesis

  摘要：

  Reduced amide pseudopeptides have been proposed as structural probes that could be useful as potential malarial vaccine components. However, designing determined pseudopeptide sequences containing isoster peptide bonds, either on an asparagine (Asn) or on a glutamine (Gln) residues, can become difficult because these precursor amino acid aldehydes are obtained in yields lower than 0.5%. This work presents a new strategy for obtaining both Asn and Gln aldehydes based on a controlled side‐chain protection approach as well as a suitable solvent partition procedure. FT‐IR, 1H‐NMR and 13C‐NMR were used for molecule characterization and identification. Amino acid aldehydes were successfully incorporated into a 20‐mer peptide from a malarial‐relevant sequence, and their impact on the molecule’s conformational properties was assessed.

  DOI：

  10.1111/j.1747-0285.2011.01182.x