methyl {methyl 3-[(methyl 3'-azido-2',3'-dideoxy-α-D-ribo-hexopyranosid)-uronamido]-2,3-dideoxy-α-D-ribo-hexopyranosid}uronate | 1033110-33-6

• 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: methyl {methyl 3-[(methyl 3'-azido-2',3'-dideoxy-α-D-ribo-hexopyranosid)-uronamido]-2,3-dideoxy-α-D-ribo-hexopyranosid}uronate
• 英文别名: methyl (2S,3S,4S,6S)-4-[[(2S,3S,4S,6S)-4-azido-3-hydroxy-6-methoxyoxane-2-carbonyl]amino]-3-hydroxy-6-methoxyoxane-2-carboxylate
• CAS: 1033110-33-6
• 化学式: C₁₅H₂₄N₄O₉
• 分子量: 404.377
• InChiKey: UYINVBOSGUKZIX-RHZLNYERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl {methyl 3-[(methyl 3'-azido-2',3'-dideoxy-α-D-ribo-hexopyranosid)-uronamido]-2,3-dideoxy-α-D-ribo-hexopyranosid}uronate 在 N-羟基-7-氮杂苯并三氮唑 、 palladium 10% on activated carbon 、 氢气 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成
  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 (methyl 3-amino-2,3-dideoxy-α-D-ribo-hexopyranosid)uronate 、 methyl 3-azido-2,3-dideoxy-α-D-ribo-hexopyranosiduronic acid 在 N-羟基-7-氮杂苯并三氮唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以53%的产率得到methyl {methyl 3-[(methyl 3'-azido-2',3'-dideoxy-α-D-ribo-hexopyranosid)-uronamido]-2,3-dideoxy-α-D-ribo-hexopyranosid}uronate
  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

文献信息

• Oligomers and peptidomimetics consisting of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids
  作者：Emilia Sikorska、Dorota Tuwalska、Przemysław Karpowicz、Elżbieta Jankowska、Andrzej Nowacki、Beata Liberek

  DOI：10.1016/j.tet.2015.02.009

  日期：2015.4

  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.
• Synthesis and conformational analysis of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids, new sugar amino acids, and their diglycotides
  作者：Dorota Tuwalska、Joanna Sienkiewicz、Beata Liberek

  DOI：10.1016/j.carres.2008.02.018

  日期：2008.5

  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.