Man9GlcNAc2Asn | 78836-79-0

• 分子结构分类: 有机化合物 - 有机聚合物 - 多糖
• 英文名称: Man9GlcNAc2Asn
• CAS: 78836-79-0
• 化学式: C₇₄H₁₂₄N₄O₅₈
• 分子量: 1997.79
• InChiKey: PIQSHKTYEDGGGJ-OMGNWVTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -25.77
• 重原子数：
  136.0
• 可旋转键数：
  37.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  991.81
• 氢给体数：
  37.0
• 氢受体数：
  58.0

反应信息

• 作为反应物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 Man9GlcNAc2Asn 在 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以40 mg的产率得到
  参考文献：
  名称：

  Efficient synthesis of glycopeptide-α-thioesters with a high-mannose type oligosaccharide by means of tert-Boc-solid phase peptide synthesis

  摘要：

  High-mannose type oligosaccharides consist of nine mannose and two N-acetylglucosamine residues (Man(9)GlcNAc(2):M9) and play an important role in protein folding processes in the endoplasmic reticulum. A highly efficient preparation method of this asparaginyl-M9-oligosaccharide from hen egg yolk was established by a two-step proteolysis with commercially available proteases and subsequent purification using high performance liquid chromatography (HPLC). To avoid the hydrolysis of the desired M9-oligosaccharide during the proteolysis steps, several commercially available proteases were screened for their contamination with mannosidases. The alpha-amino group of the resultant H2N-Asn-(M9-oligosaccharide)OH was protected with 9-fluorenylmethyloxycarbonyl (Fmoc) group for convenient separation by HPLC. The structure of Fmoc-Asn-(M9-oligosaccharide)-OH thus obtained was confirmed by ESI-MS spectrometry and several NMR experiments. Using this Fmoc-Asn-(M9-oligosaccharide)-OH, the synthesis of the M9-glycopeptide-alpha-thioester was demonstrated by means of tert-Boc-solid phase peptide synthesis. These tert-Boc conditions afforded the M9-glycopeptide-alpha-thioester in moderate yield. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.10.011

文献信息

• Chemoenzymatic synthesis of a high-mannose-type N-glycopeptide analog with C-glycosidic linkage
  作者：Wang Lai-Xi、Fan Jian-Qiang、Yuan C Lee

  DOI：10.1016/0040-4039(96)00261-4

  日期：1996.3

  A synthesis of the title compound by chemical synthesis of a GlcNAcCH2Asn containing peptide and enzymatic transfer of a Man9GlcNAc group to it was described.

  标题化合物通过GlcNAcCH的化学合成的合成2含有肽和曼的酶促转移Asn 9进行了说明的GlcNAc组给它。
• Systematic Synthesis and Binding Study of HIV V3 Glycopeptides Reveal the Fine Epitopes of Several Broadly Neutralizing Antibodies
  作者：Jared Orwenyo、Hui Cai、John Giddens、Mohammed N. Amin、Christian Toonstra、Lai-Xi Wang

  DOI：10.1021/acschembio.7b00319

  日期：2017.6.16

  both the nature and site of glycosylation in the context of the V3 domain were critical for high-affinity binding. It was found that antibody PGT128 exhibited specificity for high-mannose N-glycan with glycosylation site promiscuity, PGT121 showed binding specificity for glycopeptide carrying a sialylated N-glycan at N301 site, and 10–1074 was specific for glycopeptide carrying a high-mannose N-glycan

  最近发现了一类新的以多糖为反应性的聚糖反应性中和抗体，以PGT121、10–1074和PGT128为代表，它们靶向特定的N聚糖和V3域周围的肽区域。然而，这些bNAb的聚糖特异性和精细表位仍有待进一步定义。我们在这里报告了系统化的化学酶促合成的均质V3糖肽，其衍生自HIV-1 JR-FL株，在N332，N301和N295位携带有定义的N-聚糖。抗体结合研究表明，V3结构域中糖基化的性质和位点对于高亲和力结合至关重要。发现抗体PGT128对具有糖基化位点混杂的高甘露糖N-聚糖表现出特异性，PGT121对在N301位点携带唾液酸化的N-聚糖的糖肽具有结合特异性，10–1074特异于在N332位点带有高甘露糖N-聚糖的糖肽。合成和结合研究允许在抗体-抗原识别的背景下，对聚糖的特异性和对肽的需求进行详细的评估。鉴定出的糖肽可用作HIV疫苗设计的潜在模板。