1,3,4,6-tetra-O-acetyl-2-[(N-(carbobenzyloxy)-L-phenylalanyl)amino]-2-deoxy-β-D-glucopyranose | 141280-15-1

• 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: 1,3,4,6-tetra-O-acetyl-2-[(N-(carbobenzyloxy)-L-phenylalanyl)amino]-2-deoxy-β-D-glucopyranose
• 英文别名: 2-(N-carbobenzyloxy)-L-phenylalanylamido-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucose
• CAS: 141280-15-1
• 化学式: C₃₁H₃₆N₂O₁₂
• 分子量: 628.633
• InChiKey: USRQILYKDHEMTL-HEBNFACKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  45.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  181.86
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-[(N-(carbobenzyloxy)-L-phenylalanyl)amino]-2-deoxy-β-D-glucopyranose 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 以70%的产率得到2-(N-carbobenzyloxy)-L-phenylalanylamido-2-deoxy-β-D-glucose
  参考文献：
  名称：

  Synthesis and properties of d-glucosamine N-peptidyl derivatives as substrate analog inhibitors of papain and cathepsin B

  摘要：

  N-peptidyl derivatives of D-glucosamine 7c-7n were synthesized and tested as 7c-7n were synthesized and tested as reversible, substrate analog inhibitors of cysteine and serine-proteases. D-Glucosamine itself showed fair inhibiting properties against cysteine-proteases. Derivatives 7c-7i, designed to improve binding at papain active site, displayed reversible inhibition with K(i) ranging from 67-860-mu-M for papain and from 111-2400-mu-M for cathepsin B. Representative serine proteases were unaffected. No inhibitory activity against human leukocyte elastase was observed for derivatives 7m and 7n bearing very effective peptidyl recognizing units for this enzyme.

  DOI：

  10.1016/0223-5234(91)90001-4
• 作为产物：
  描述：

  在 吡啶 、 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 18.0h， 生成 1,3,4,6-tetra-O-acetyl-2-[(N-(carbobenzyloxy)-L-phenylalanyl)amino]-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis and characterisation of glucosamine–NSAID bioconjugates

  摘要：

  合成策略以制备非甾体抗炎药物 - 葡萄糖胺生物结合物。

  DOI：

  10.1039/c4ob01681e

文献信息

• N-Acetyl-l-phenylalanine Racemization during TBTU Amidation: An In-Depth Study for the Synthesis of Anti-Inflammatory 2-(N-Acetyl)-l-phenylalanylamido-2-deoxy-d-glucose (NAPA)
  作者：Elisa Sturabotti、Fabrizio Vetica、Giorgia Toscano、Andrea Calcaterra、Andrea Martinelli、Luisa Maria Migneco、Francesca Leonelli

  DOI：10.3390/molecules28020581

  日期：——

  A thorough study on the amidation conditions of N-acetyl-l-phenylalanine using TBTU and various bases is reported for the synthesis of 2-(N-acetyl)-l-phenylalanylamido-2-deoxy-d-glucose (NAPA), a promising drug for the treatment of joints diseases. TBTU-mediated diastereoselective amidation reaction with 1,3,4,6-tetra-O-acetyl-β-d-glucosamine always gave racemization of N-acetyl-l-phenylalanine. The

  据报道，使用 TBTU 和各种碱对 N-乙酰-l-苯丙氨酸的酰胺化条件进行了全面研究，以合成 2-(N-乙酰基)-l-苯丙氨酰氨基-2-脱氧-d-葡萄糖 (NAPA)，一种用于治疗关节疾病的有前途的药物。TBTU 介导的与 1,3,4,6-四-O-乙酰基-β-d-葡糖胺的非对映选择性酰胺化反应总是产生 N-乙酰基-1-苯丙氨酸的外消旋化。在存在不同碱基的情况下并通过其他对照实验详细研究了酰胺化条件下的立体化学保留，证明了使用吡啶作为碱基减少外消旋化的可能性。