methyl 3-amino-2,3-dideoxy-α-D-arabino-hexopyranosiduronic acid | 1033110-21-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-amino-2,3-dideoxy-α-D-arabino-hexopyranosiduronic acid
• 英文别名: (2S,3S,4R,6S)-4-amino-3-hydroxy-6-methoxyoxane-2-carboxylic acid
• CAS: 1033110-21-2
• 化学式: C₇H₁₃NO₅
• 分子量: 191.184
• InChiKey: QTABLOPHDOQHLT-VANKVMQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.48
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  102.01
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 3-amino-2,3-dideoxy-α-D-arabino-hexopyranosiduronic acid 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以58%的产率得到methyl N-Fmoc-3-amino-2,3-dideoxy-α-D-arabino-hexopyranosiduronic acid
  参考文献：
  名称：

  Oligomers and peptidomimetics consisting of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids

  摘要：

  In search of new foldamers, the synthesis of homo and heterooligomeric tetramers, consisting of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids, from the respective dimers, is presented. Both the dimers and tetramers were subjected to molecular dynamics simulations, based on NOE interactions. These show the preferred conformations of presented sugar amino acids (SAAs) oligomers. The CD spectra of these oligomers depend on the configuration of the C3 carbon atom bearing the amide chromophore. Next, the syntheses of two peptidomimetics with SAA incorporated into a peptide chain, are presented. A Leu-enkephalin mimetic was subjected to molecular dynamics simulations, which show how a SAA influences the geometry of a peptidomimetic. A Tat1 protein mimetic is demonstrated to display an inhibitory influence on the activity of a proteasome. Its structure is studied on a basis of the CD and FTIR spectra. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.02.009
• 作为产物：
  描述：

  methyl (2S,3S,4R,6S)-4-amino-3-hydroxy-6-methoxyoxane-2-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以76%的产率得到methyl 3-amino-2,3-dideoxy-α-D-arabino-hexopyranosiduronic acid
  参考文献：
  名称：

  Synthesis and conformational analysis of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids, new sugar amino acids, and their diglycotides

  摘要：

  The synthesis of methyl 3-azido- and 3-amino-2,3-dideoxyhexopyranosiduronic acids and their methyl esters with the -alpha,beta-D-arabino-, -alpha,beta-D-ribo, and -alpha,beta-L-lyxo configurations is presented. The conformations of the synthesized sugar amino acids and their precursors are discussed on the basis of H-1 NMR data. The influence of the 5-carboxyl group on the pyranose ring conformation is assessed, and the bonding of the monosugar amino acids into dimeric glycotides, using conventional solution-phase peptide syntheses, is reported. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.02.018