[α-D-mannopyranosyl-(1→3)]-[[α-D-mannopyranosyl-(1→3)]-[α-D-mannopyranosyl-(1→6)]-α-D-mannopyranosyl-(1→6)]-β-D-mannopyranosyl-(1→4)-2-deoxy-2-N-acetyl-β-D-glucopyranosyl-(1→4)-2-deoxy-2-N-acetyl-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [α-D-mannopyranosyl-(1→3)]-[[α-D-mannopyranosyl-(1→3)]-[α-D-mannopyranosyl-(1→6)]-α-D-mannopyranosyl-(1→6)]-β-D-mannopyranosyl-(1→4)-2-deoxy-2-N-acetyl-β-D-glucopyranosyl-(1→4)-2-deoxy-2-N-acetyl-α-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3S,4S,5R,6R)-6-[[(2S,3S,4S,5R,6R)-3,5-dihydroxy-4-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]-3,5-dihydroxy-4-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₄₆H₇₈N₂O₃₆
• 分子量: 1235.12
• InChiKey: XWWHPWNSSSAMOV-LIEBSNBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -14.4
• 重原子数：
  84
• 可旋转键数：
  21
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  603
• 氢给体数：
  23
• 氢受体数：
  36

反应信息

• 作为反应物：
  描述：

  异烟肼 、 [α-D-mannopyranosyl-(1→3)]-[[α-D-mannopyranosyl-(1→3)]-[α-D-mannopyranosyl-(1→6)]-α-D-mannopyranosyl-(1→6)]-β-D-mannopyranosyl-(1→4)-2-deoxy-2-N-acetyl-β-D-glucopyranosyl-(1→4)-2-deoxy-2-N-acetyl-α-D-glucopyranoside 以 甲醇 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  异烟肼及其生物素化形式衍生的N-聚糖的基质辅助激光解吸/电离串联质谱。

  摘要：

  理据聚糖的成功结构表征通常需要在质谱分析之前进行衍生化。在这里，我们报告了一种用于聚糖的新型衍生试剂，生物素化的异烟酸酰肼，可通过质谱（MS）和生化方法进行聚糖分析。研究了MS中的碎片行为及其在结构阐明中的用途，并将其与其他标记进行了比较。方法用核糖核酸酶B和卵清蛋白释放的聚糖用肼标记（异烟肼（INH），生物素化的异烟酸酰肼（BINH）和生物素氨基丙酰肼（BACH））衍生化。另外，制备了天然对应物和2-氨基苯甲酰胺（2-AB）衍生物。进行了比较基质辅助的激光解吸/电离串联飞行时间（MALDI TOF / TOF）实验，以研究衍生物的碎片模式。最后，探索了BINH衍生物结合凝集素的能力。结果通常，与天然对口相比，衍生化在质谱信号强度方面提供了有益的增强。质谱碎裂随所用标记的种类而异。在BINH衍生物的光谱中观察到最显着的结构揭示离子（交叉环断裂），而主要发现的糖苷断裂是天然形式的聚糖和2-A

  DOI：

  10.1002/rcm.6955
• 作为产物：
  描述：

  在 20% palladium hydroxide-activated charcoal 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 [α-D-mannopyranosyl-(1→3)]-[[α-D-mannopyranosyl-(1→3)]-[α-D-mannopyranosyl-(1→6)]-α-D-mannopyranosyl-(1→6)]-β-D-mannopyranosyl-(1→4)-2-deoxy-2-N-acetyl-β-D-glucopyranosyl-(1→4)-2-deoxy-2-N-acetyl-β-D-glucopyranoside 、 [α-D-mannopyranosyl-(1→3)]-[[α-D-mannopyranosyl-(1→3)]-[α-D-mannopyranosyl-(1→6)]-α-D-mannopyranosyl-(1→6)]-β-D-mannopyranosyl-(1→4)-2-deoxy-2-N-acetyl-β-D-glucopyranosyl-(1→4)-2-deoxy-2-N-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  Chemical Synthesis of Highly Congested gp120 V1V2 N-Glycopeptide Antigens for Potential HIV-1-Directed Vaccines

  摘要：

  Critical to the search for an effective HIV-1 vaccine is the development of immunogens capable of inducing broadly neutralizing antibodies (BnAbs). A key first step in this process is to design immunogens that can be recognized by known BnAbs. The monoclonal antibody PG9 is a BnAb that neutralizes diverse strains of HIV-1 by targeting a conserved carbohydrate protein epitope in the variable 1 and 2 (V1V2) region of the viral envelope. Important for recognition are two closely spaced N-glycans at Asn(160) and Asn(156). Glycopeptides containing this synthetically challenging bis-N-glycosylated motif were prepared by convergent assembly, and were shown to be antigenic for PG9. Synthetic glycopeptides such as these may be useful for the development of HIV-1 vaccines based on the envelope V1V2 BnAb epitope.

  DOI：

  10.1021/ja405990z

文献信息

• Chemical Synthesis of Highly Congested gp120 V1V2 <i>N</i>-Glycopeptide Antigens for Potential HIV-1-Directed Vaccines
  作者：Baptiste Aussedat、Yusuf Vohra、Peter K. Park、Alberto Fernández-Tejada、S. Munir Alam、S. Moses Dennison、Frederick H. Jaeger、Kara Anasti、Shelley Stewart、Julie H. Blinn、Hua-Xin Liao、Joseph G. Sodroski、Barton F. Haynes、Samuel J. Danishefsky

  DOI：10.1021/ja405990z

  日期：2013.9.4

  Critical to the search for an effective HIV-1 vaccine is the development of immunogens capable of inducing broadly neutralizing antibodies (BnAbs). A key first step in this process is to design immunogens that can be recognized by known BnAbs. The monoclonal antibody PG9 is a BnAb that neutralizes diverse strains of HIV-1 by targeting a conserved carbohydrate protein epitope in the variable 1 and 2 (V1V2) region of the viral envelope. Important for recognition are two closely spaced N-glycans at Asn(160) and Asn(156). Glycopeptides containing this synthetically challenging bis-N-glycosylated motif were prepared by convergent assembly, and were shown to be antigenic for PG9. Synthetic glycopeptides such as these may be useful for the development of HIV-1 vaccines based on the envelope V1V2 BnAb epitope.
• Matrix-assisted laser desorption/ionization tandem mass spectrometry of <i>N</i> -glycans derivatized with isonicotinic hydrazide and its biotinylated form
  作者：Stephanie Bank、Eberhard Heller、Elisabeth Memmel、Jürgen Seibel、Ulrike Holzgrabe、Petra Kapková

  DOI：10.1002/rcm.6955

  日期：2014.8.15

  derivatives to bind lectins was explored. RESULTS Generally, derivatization provided beneficial enhancement in the mass spectrometric signal intensity as compared to native counterparts. The mass spectrometric fragmentation varied with the kind of label used. The most significant structure-revealing ions (cross-ring cleavages) were observed in the spectra of BINH derivatives, whereas mainly glycosidic cleavages

  理据聚糖的成功结构表征通常需要在质谱分析之前进行衍生化。在这里，我们报告了一种用于聚糖的新型衍生试剂，生物素化的异烟酸酰肼，可通过质谱（MS）和生化方法进行聚糖分析。研究了MS中的碎片行为及其在结构阐明中的用途，并将其与其他标记进行了比较。方法用核糖核酸酶B和卵清蛋白释放的聚糖用肼标记（异烟肼（INH），生物素化的异烟酸酰肼（BINH）和生物素氨基丙酰肼（BACH））衍生化。另外，制备了天然对应物和2-氨基苯甲酰胺（2-AB）衍生物。进行了比较基质辅助的激光解吸/电离串联飞行时间（MALDI TOF / TOF）实验，以研究衍生物的碎片模式。最后，探索了BINH衍生物结合凝集素的能力。结果通常，与天然对口相比，衍生化在质谱信号强度方面提供了有益的增强。质谱碎裂随所用标记的种类而异。在BINH衍生物的光谱中观察到最显着的结构揭示离子（交叉环断裂），而主要发现的糖苷断裂是天然形式的聚糖和2-A