methyl 1-N-acetamido-2,3,4-tri-O-acetyl-β-D-galacturonate | 1467116-15-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 1-N-acetamido-2,3,4-tri-O-acetyl-β-D-galacturonate
• CAS: 1467116-15-9
• 化学式: C₁₅H₂₁NO₁₀
• 分子量: 375.332
• InChiKey: BHWWPCKSSTVNQR-MQLXINIDSA-N

反应信息

• 作为反应物：
  描述：

  methyl 1-N-acetamido-2,3,4-tri-O-acetyl-β-D-galacturonate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以21%的产率得到N-(β-D-galacturonopyranosyl)acetamide
  参考文献：
  名称：

  Synthesis of N-(β-d-glycuronopyranosyl)alkanamides and 1-(β-d-glycuronopyranosyl)-4-phenyl-[1,2,3]-triazoles as N-glycoprotein linkage region analogs: examination of the effect of C5 substituent on the N-glycosidic torsion (ΦN) based on X-ray crystallography

  摘要：

  The torsion angle around the N-glycoprotein linkage region (GlcNAc-Asn) is an important factor for presenting sugar on the cell surface which is crucial for many biological processes. Earlier studies using model and analogs showed that this important torsion angle is greatly influenced by substitutions in the sugar part. In the present work, uronic acid alkanamides and triazole derivatives have been designed and synthesized as newer analogs of N-glycoprotein linkage region to understand the influence of the carboxylic group on linkage region torsion as well as on molecular packing. Crystal structure of N-(beta-D-galacturonopyranosyl)acetamide is solved with the space group of P22(1)2(1). Comparison of the torsion angle and molecular packing of this compound with N-(beta-D-galactopyranosyl)acetamide showed that changing the C6-hydoxymethyl group to the carboxylic acid group has minimum influence on the N-glycosidic torsion angle, Phi(N) and significant influence on the molecular packing. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.06.023
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-galactopyranuronate 在 吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 methyl 1-N-acetamido-2,3,4-tri-O-acetyl-β-D-galacturonate
  参考文献：
  名称：

  Synthesis of N-(β-d-glycuronopyranosyl)alkanamides and 1-(β-d-glycuronopyranosyl)-4-phenyl-[1,2,3]-triazoles as N-glycoprotein linkage region analogs: examination of the effect of C5 substituent on the N-glycosidic torsion (ΦN) based on X-ray crystallography

  摘要：

  The torsion angle around the N-glycoprotein linkage region (GlcNAc-Asn) is an important factor for presenting sugar on the cell surface which is crucial for many biological processes. Earlier studies using model and analogs showed that this important torsion angle is greatly influenced by substitutions in the sugar part. In the present work, uronic acid alkanamides and triazole derivatives have been designed and synthesized as newer analogs of N-glycoprotein linkage region to understand the influence of the carboxylic group on linkage region torsion as well as on molecular packing. Crystal structure of N-(beta-D-galacturonopyranosyl)acetamide is solved with the space group of P22(1)2(1). Comparison of the torsion angle and molecular packing of this compound with N-(beta-D-galactopyranosyl)acetamide showed that changing the C6-hydoxymethyl group to the carboxylic acid group has minimum influence on the N-glycosidic torsion angle, Phi(N) and significant influence on the molecular packing. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.06.023