2-acetamido-3,4,6-tri-O-acetyl-1-N-[α-(carbobenzyloxy)-β-aspartyl]-2-deoxy-β-D-glucopyranosylamine | 38877-33-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-acetamido-3,4,6-tri-O-acetyl-1-N-[α-(carbobenzyloxy)-β-aspartyl]-2-deoxy-β-D-glucopyranosylamine
• 英文别名: (2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]amino]-4-oxo-2-(phenylmethoxycarbonylamino)butanoic acid
• CAS: 38877-33-7
• 化学式: C₂₆H₃₃N₃O₁₃
• 分子量: 595.56
• InChiKey: RGTDYWCYMHIIFH-FNMCVODLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  222
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-1-N-[α-(carbobenzyloxy)-β-aspartyl]-2-deoxy-β-D-glucopyranosylamine 在 palladium on activated charcoal 水 、 氢气 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 30.5h， 生成 2-acetamido-3,4,6-tri-O-acetyl-1-N-<(aspartylleucylthreoninamid)-4.1-yl>-2-deoxy-β-D-glucopyranosylamine
  参考文献：
  名称：

  Yeast oligosaccharyltransferase: glycosylation of peptide substrates and chemical characterization of the glycopeptide product

  摘要：

  The product of the reaction catalyzed by yeast oligosaccharyltransferase was examined in order to determine the nature of the chemical linkage between the sugar and peptide. Biosynthetic donor lipid [H-3]oligosaccharide was prepared and used as a substrate for yeast oligosaccharyltransferase together with a chemically synthesized peptide acceptor, N-benzoyl-Asn-Leu-Thr-NH2. the glycosylated peptide product of the in vitro reaction was isolated and hydrolyzed with endo-beta-N-acetylglucosaminidase-H to yield a large oligosaccharide and the glycotripeptide, N-benzoyl-Asn(GlcNAc)-Leu-Thr-Nh2. This glycopeptide was purified using gel filtration, affinity binding, and reverse-phase high-performance liquid chromatography. The biosynthetic glycopeptide was compared with chemically synthesized glycopeptides in which a 1-amino-GlcNAc moiety was linked to either the alpha- or beta-carboxyl of aspartate. It was determined that the sole biosynthetic product has the structure in which the carbohydrate is linked to the peptide through the beta-carbonyl of asparagine, i.e., a normal alpha-peptide. These experiments provide an unambiguous structural proof of the protein-carbohydrate linkage in the glycoprotein product of the oligosaccharyltransferase-catalyzed reaction.

  DOI：

  10.1021/jo00313a013
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-Β-D-吡喃葡萄糖酰基叠氮化物 在 ammonium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 2-acetamido-3,4,6-tri-O-acetyl-1-N-[α-(carbobenzyloxy)-β-aspartyl]-2-deoxy-β-D-glucopyranosylamine
  参考文献：
  名称：

  Yeast oligosaccharyltransferase: glycosylation of peptide substrates and chemical characterization of the glycopeptide product

  摘要：

  The product of the reaction catalyzed by yeast oligosaccharyltransferase was examined in order to determine the nature of the chemical linkage between the sugar and peptide. Biosynthetic donor lipid [H-3]oligosaccharide was prepared and used as a substrate for yeast oligosaccharyltransferase together with a chemically synthesized peptide acceptor, N-benzoyl-Asn-Leu-Thr-NH2. the glycosylated peptide product of the in vitro reaction was isolated and hydrolyzed with endo-beta-N-acetylglucosaminidase-H to yield a large oligosaccharide and the glycotripeptide, N-benzoyl-Asn(GlcNAc)-Leu-Thr-Nh2. This glycopeptide was purified using gel filtration, affinity binding, and reverse-phase high-performance liquid chromatography. The biosynthetic glycopeptide was compared with chemically synthesized glycopeptides in which a 1-amino-GlcNAc moiety was linked to either the alpha- or beta-carboxyl of aspartate. It was determined that the sole biosynthetic product has the structure in which the carbohydrate is linked to the peptide through the beta-carbonyl of asparagine, i.e., a normal alpha-peptide. These experiments provide an unambiguous structural proof of the protein-carbohydrate linkage in the glycoprotein product of the oligosaccharyltransferase-catalyzed reaction.

  DOI：

  10.1021/jo00313a013

文献信息

• Comparative Lipase-Catalyzed Hydrolysis of Ethylene Glycol Derived Esters. The 2-Methoxyethyl Ester as a Protective Group in Peptide and Glycopeptide Synthesis
  作者：Markus Gewehr、Horst Kunz

  DOI：10.1055/s-1997-1374

  日期：1997.12

  Comparison of the lipase-catalyzed cleavage of polar esters derived from ethylene glycol proved 2-methoxyethyl (ME) esters most favorable protecting groups for the carboxylic function of peptides and glycopeptides. They combine high substrate acceptance and high yields of hydrolysis with favorable physiochemical properties and advantageous solubility. The application of this polar ester as protecting group was extended to N-glycosylated amino acids and N-glycopeptides. The selective removal of ME esters by lipases was achieved under mild conditions (pH 7.0 and 37°C), leaving all other linkages including peptide bonds and other ester protecting groups unaffected.

  乙二醇衍生的极性酯在脂肪酶催化下的水解比较表明，2-甲氧乙基（ME）酯是肽和糖肽的羧基功能基团最有利的保护基。它们结合了高底物接受性和高水解产率，同时具有良好的物理化学特性和优越的溶解性。该极性酯作为保护基的应用扩展到N-糖基化氨基酸和N-糖肽。在温和条件下（pH 7.0和37°C），有效地选择性去除ME酯，而不影响其他连接，包括肽键和其他酯保护基。
• Synthesis of glycopeptides containing the amino acid sequence 17-23 of bovine pancreatic deoyxribonuclease
  作者：Hari G. Garg、Roger W. Jeanloz

  DOI：10.1016/s0008-6215(00)84581-4

  日期：1980.11

  6-tri-O-acetyl-1-N-[N-benzyloxycarbonyl)-L-aspart-1-oyl-(L-alan yl-L-threonyl-L-leucyl-L-alanyl-L-serine p-nitrobenzyl ester)-4-oyl]-2-deoxy-beta-D-glucopyranosylamine (7), which span the amino acid sequence 17-23 of bovine pancreatic deoxyribonuclease A and contain a 2-acetamido-2-deoxy-D-glucose residue, were synthesized. On treatment with lithium hydroxide, the blocked glycohexapeptide 7 gave 2-acetamido-1-N-[N

  2-乙酰氨基-3,4,6-三-O-乙酰基-1-N- [N-（苄氧羰基-L-丝氨酰）-L-天冬氨酸-1-基-（对硝基苄基酯）-4-基] -2-脱氧-β-D-吡喃葡萄糖胺，2-乙酰氨基-3,4,6-三-O-乙酰基-1-N- [N-（苄氧羰基-L-丝氨酰）-L-天冬氨酸-1-oyl -（L-丙氨酸甲酯）-4-酰基] -2-脱氧-β-D-吡喃葡萄糖胺和2-乙酰氨基-3,4,6-三-O-乙酰基-1-N- [N-苄氧基羰基） -L-天门冬氨酰基-（L-丙氨酰基-L-苏氨酰基-L-亮氨酸-L-丙氨酰基-L-丝氨酸对硝基苄基酯）-4-Oyl] -2-脱氧-β-D-吡喃葡萄糖胺合成了（7），其跨越牛胰腺脱氧核糖核酸酶A的氨基酸序列17-23，并且包含2-乙酰氨基-2-脱氧-D-葡萄糖残基。用氢氧化锂处理后