O-α-D-mannopyranosyl-(1->3)-6)>-O-β-D-mannopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-α-D-glucopyranose | 92733-54-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-α-D-mannopyranosyl-(1->3)-6)>-O-β-D-mannopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-α-D-glucopyranose
• 英文别名: [α-D-mannopyranosyl-(1→3)]-[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；Man(a1-3)[Man(a1-6)]Man(b1-4)GlcNAc(b1-4)a-GlcNAc；N-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(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]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 92733-54-5
• 化学式: C₃₄H₅₈N₂O₂₆
• 分子量: 910.832
• InChiKey: ZTOKCBJDEGPICW-KGZZHXLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.6
• 重原子数：
  62
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  445
• 氢给体数：
  17
• 氢受体数：
  26

反应信息

• 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 O-α-D-mannopyranosyl-(1->3)-6)>-O-β-D-mannopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranose 、 O-α-D-mannopyranosyl-(1->3)-6)>-O-β-D-mannopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-α-D-glucopyranose
  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

• Synthese der invarianten pentasaccharid-core-region der kohlenhydrat-ketten der N-glycoproteine
  作者：Hans Paulsen、Rolf Lebuhn

  DOI：10.1016/0008-6215(84)85272-6

  日期：1984.7

  linkage gave a trisaccharide that was deblocked to yield O -β- d -mannopyranosyl-(1→4)- O -(2-acetamido-2-deoxy-β- d -glucopyranosyl)-(1→4)-2-acetamido-2-deoxy- d -glucopyranose. Condensation of benzyl O -(2,4-di- O -benzyl-β- d -mannopyranosyl)-(1→4)- O -(6- O -acetyl-3- O -benzyl-2-deoxy-2-phthalimido-β- d -glucopyranosyl)-(1 →4)-2-acetamido-3,6-di- O -benzyl-2-deoxy-α- d -glucopyranoside with an excess

  摘要6-O-乙酰基-3-O-苄基-2-脱氧-4-O-（3,6-二-O-烯丙基-2,4-二-O-苄基-β-d-甘露吡喃糖基）-2由1,6-脱水-2-叠氮基-3-O-苄基-2-脱氧-4-O-（6-O）经五步反应合成了邻苯二甲酰亚胺-β-d-吡喃葡萄糖基氯（9）。 -乙酰基-3-O-烯丙基-2，4-二-O-苄基-β-d-甘露吡喃糖基）-β-d-葡糖吡喃糖。9与苄基2-乙酰氨基-3,6-二-O-苄基-2-脱氧-α-d-吡喃葡萄糖苷的嵌段合成形成β-d-糖苷键得到三糖，该三糖被解封以生成O-β- d-甘露吡喃糖基-（1→4）-O-（2-乙酰氨基-2-脱氧-β-d-吡喃吡喃糖基）-（1→4）-2-乙酰胺基-2-脱氧-d-吡喃葡萄糖。苄基O-（2,4-二-O-苄基-β-d-甘露吡喃糖基）-（1→4）-O-（6-O-乙酰基-3-O-苄基-2-脱氧-2-基的缩合邻苯二甲酰亚胺基-β-d-吡喃葡萄糖基）-（1→4）-2-乙酰氨基-3，
• 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.