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 | 81098-56-8

• 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-β-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-β-D-glucopyranoside；alpha-D-Manp-(1->3)-[alpha-D-Manp-(1->6)]-beta-D-Manp-(1->4)-beta-D-GlcpNAc-(1->4)-beta-D-GlcpNAc；N-[(2R,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: 81098-56-8
• 化学式: C₃₄H₅₈N₂O₂₆
• 分子量: 910.832
• InChiKey: ZTOKCBJDEGPICW-GWPISINRSA-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 palladium on activated charcoal sodium methylate 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 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
  参考文献：
  名称：

  Thermodynamic Analysis of Interactions between N-Linked Sugar Chains and F-Box Protein Fbs1

  摘要：

  Fbs1 is a recently discovered F-box protein that was proposed to recognize high-mannose-type asparagine-linked glycoprotein sugar chains. To reveal the specificity of Fbs1, Man alpha 1 -> 6Man beta 1 -> 4GlcNAc(2), Man alpha 1 -> 3Mar beta -> 4GlcNAc(2), and Man alpha 1 -> 3(Man alpha 1 -> 6)Man beta 1 -> 4GlcNAc(2) were synthesized and their affinities for Fbs1 were evaluated in comparison with previously synthesized Man(9)GlcNAc(2) and Man(8)GlcNAc(2). These analyses revealed that Man(3)GlcNAc(2) had the strongest affinity and the chitobiose and alpha 1 -> 6 linked Man residue are necessary for Fbs1 to recognize a sugar.

  DOI：

  10.1021/jm0489511

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.
• Thermodynamic Analysis of Interactions between N-Linked Sugar Chains and F-Box Protein Fbs1
  作者：Shinya Hagihara、Kiichiro Totani、Ichiro Matsuo、Yukishige Ito

  DOI：10.1021/jm0489511

  日期：2005.5.1

  Fbs1 is a recently discovered F-box protein that was proposed to recognize high-mannose-type asparagine-linked glycoprotein sugar chains. To reveal the specificity of Fbs1, Man alpha 1 -> 6Man beta 1 -> 4GlcNAc(2), Man alpha 1 -> 3Mar beta -> 4GlcNAc(2), and Man alpha 1 -> 3(Man alpha 1 -> 6)Man beta 1 -> 4GlcNAc(2) were synthesized and their affinities for Fbs1 were evaluated in comparison with previously synthesized Man(9)GlcNAc(2) and Man(8)GlcNAc(2). These analyses revealed that Man(3)GlcNAc(2) had the strongest affinity and the chitobiose and alpha 1 -> 6 linked Man residue are necessary for Fbs1 to recognize a sugar.