3-C-[(N-benzyloxycarbonylglycyl)aminomethyl]-3-[(carboxymethyl)amino]-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose | 1012796-20-1

• 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: 3-C-[(N-benzyloxycarbonylglycyl)aminomethyl]-3-[(carboxymethyl)amino]-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
• 英文别名: 2-[[(3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-[[[2-(phenylmethoxycarbonylamino)acetyl]amino]methyl]-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-yl]amino]acetic acid
• CAS: 1012796-20-1
• 化学式: C₂₅H₃₅N₃O₁₀
• 分子量: 537.567
• InChiKey: RDAZHVIKPLOYDH-XOFWXVISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  163
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3-C-[(N-benzyloxycarbonylglycyl)aminomethyl]-3-[(carboxymethyl)amino]-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 、 3-酞酰亚胺基丙酸甲酯 在 N-羟基丁二酰亚胺 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.0h， 以67%的产率得到3-C-[(N-benzyloxycarbonylglycyl)aminomethyl]-3-deoxy-1,2:5,6-di-O-isopropylidene-3-[({[(S)-1-(methoxycarbonyl)ethyl]amino}carbonyl)methylamino]-α-D-allofuranose
  参考文献：
  名称：

  Novel glycine like amino acids from glyco-α-aminonitriles as building blocks for peptide synthesis

  摘要：

  Our interest in the glycoaminocyanation reaction led us to apply this methodology to introduce amino acids on a monosaccharide using the N-terminal position. The GAAs described in this paper are characterized by having the amino and carboxylic acid functionalities on a disubstituted position of the saccharide backbone leading to alpha,alpha-disubstituted glycines. These new sugar amino acids showed a restricted conformation involving a spontaneous intramolecular cyclization between the C- and N-terminal positions during hydrolysis or hydrogenolysis to give the corresponding oxopiperazine. Tripeptide mimics were obtained by the introduction of an additional amino acid using one-pot conditions starting from these cyclic by-products under basic media. We demonstrated that these pseudo tripeptides are good candidates for extension of the peptidic scaffold and cyclization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.038
• 作为产物：
  描述：

  N-苄氧羰基甘氨酸-4-硝基苯酯 、 (3R)-1,2:5,6-di-O-isopropylidene-spiro[3-deoxy-α-D-ribohexofuranose-3,5'-piperazine]-2'-one 在 sodium hydroxide 、 水 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 以56%的产率得到3-C-[(N-benzyloxycarbonylglycyl)aminomethyl]-3-[(carboxymethyl)amino]-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
  参考文献：
  名称：

  Novel glycine like amino acids from glyco-α-aminonitriles as building blocks for peptide synthesis

  摘要：

  Our interest in the glycoaminocyanation reaction led us to apply this methodology to introduce amino acids on a monosaccharide using the N-terminal position. The GAAs described in this paper are characterized by having the amino and carboxylic acid functionalities on a disubstituted position of the saccharide backbone leading to alpha,alpha-disubstituted glycines. These new sugar amino acids showed a restricted conformation involving a spontaneous intramolecular cyclization between the C- and N-terminal positions during hydrolysis or hydrogenolysis to give the corresponding oxopiperazine. Tripeptide mimics were obtained by the introduction of an additional amino acid using one-pot conditions starting from these cyclic by-products under basic media. We demonstrated that these pseudo tripeptides are good candidates for extension of the peptidic scaffold and cyclization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.038

文献信息

• Novel glycine like amino acids from glyco-α-aminonitriles as building blocks for peptide synthesis
  作者：Hélène Ducatel、Albert Nguyen Van Nhien、Denis Postel

  DOI：10.1016/j.tetasy.2007.11.038

  日期：2008.1

  Our interest in the glycoaminocyanation reaction led us to apply this methodology to introduce amino acids on a monosaccharide using the N-terminal position. The GAAs described in this paper are characterized by having the amino and carboxylic acid functionalities on a disubstituted position of the saccharide backbone leading to alpha,alpha-disubstituted glycines. These new sugar amino acids showed a restricted conformation involving a spontaneous intramolecular cyclization between the C- and N-terminal positions during hydrolysis or hydrogenolysis to give the corresponding oxopiperazine. Tripeptide mimics were obtained by the introduction of an additional amino acid using one-pot conditions starting from these cyclic by-products under basic media. We demonstrated that these pseudo tripeptides are good candidates for extension of the peptidic scaffold and cyclization. (c) 2007 Elsevier Ltd. All rights reserved.