Man(a1-3)[Man(a1-6)]Man(b1-4)GlcNAc(b1-4)b-GlcNAc1N | 312967-43-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Man(a1-3)[Man(a1-6)]Man(b1-4)GlcNAc(b1-4)b-GlcNAc1N
• 英文别名: 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-amino-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 312967-43-4
• 化学式: C₃₄H₅₉N₃O₂₅
• 分子量: 909.848
• InChiKey: VNQRWJQFEIGBJC-GWPISINRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.9
• 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：
  451
• 氢给体数：
  17
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  Man(a1-3)[Man(a1-6)]Man(b1-4)GlcNAc(b1-4)b-GlcNAc1N 在 哌啶 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Tight binding ligand approach to oligosaccharide-grafted protein

  摘要：

  A novel type of artificial glycoprotein was developed, by using dihydrofolate reductase (DHFR) and methotrexate (MTX) as a protein-ligand pair. Various oligosaccharides linked to MTX were shown to bind tightly with DHFR and afforded oligosaccharide-grafted protein, which could be isolated easily by lectin beads. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.106
• 作为产物：
  描述：

  α-D-mannopyranosyl-(1<*>6)-<α-D-mannopyranosyl-(1<*>3)>-β-D-mannopyranosyl-(1<*>4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1<*>4)-2-acetamido-2-deoxy-D-glucopyranose 在 碳酸氢铵 作用下， 以 水 为溶剂， 以100%的产率得到Man(a1-3)[Man(a1-6)]Man(b1-4)GlcNAc(b1-4)b-GlcNAc1N
  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

• Toward Fully Synthetic Glycoproteins by Ultimately Convergent Routes:  A Solution to a Long-Standing Problem
  作者：J. David Warren、Justin S. Miller、Stacy J. Keding、Samuel J. Danishefsky

  DOI：10.1021/ja0491836

  日期：2004.6.1

  A method is disclosed for the convergent synthesis of multiply glycosylated peptides. The approach centers on a convergent technique for generating masked, complex glycopeptide-containing C-terminal acyl donors. Activation of the latent donor in situ and use directly in segment coupling with a second peptide bearing a complex carbohydrate produces a completely unprotected, bifunctional glycopeptide

  公开了一种用于多重糖基化肽的会聚合成的方法。该方法的中心是用于生成掩蔽的、复杂的含糖肽的 C 端酰基供体的收敛技术。原位激活潜在供体并直接用于与带有复杂碳水化合物的第二个肽偶联的片段，产生完全不受保护的双功能糖肽。该系统在完全收敛的片段偶联过程中，在酰基供体的 C 端氨基酸残基处显示出最低水平的水解和差向异构化，因此是合成糖蛋白的有力工具。
• A highly convergent synthesis of an N-linked glycopeptide presenting the H-type 2 human blood group determinant
  作者：Zhi-Guang Wang、J. David Warren、Vadim Y. Dudkin、Xufang Zhang、Ulrich Iserloh、Michael Visser、Matthias Eckhardt、Peter H. Seeberger、Samuel J. Danishefsky

  DOI：10.1016/j.tet.2006.02.080

  日期：2006.5

  The total synthesis of an H-type blood group determinant in a model biological setting is described. The construct is comprised of a high mannose core structure with projecting lactose spacers, culminating in a two-copy presentation of the H-type blood group determinant itself. Key reactions that were used in this construction include sulfonamidohydroxylation (see 15 -> 18) and benzoate-directed glycosylation via an activated thiophenyl donor (see 34 -> 36). Another key strategic element involved the epimerization of an interior core glucoside to reach the P-mannoside (see 37 -> 38) required in the ring C sugar of the high mannose core. (c) 2006 Elsevier Ltd. All rights reserved.
• From Glycals to Glycopeptides: A Convergent and Stereoselective Total Synthesis of a High Mannose N-Linked Glycopeptide
  作者：Zhi-Guang Wang、XuFang Zhang、David Live、Samuel J. Danishefsky

  DOI：10.1002/1521-3773(20001016)39:20<3652::aid-anie3652>3.0.co;2-b

  日期：2000.10.16
• Reiterative cysteine-based coupling leading to complex, homogeneous glycopeptides
  作者：Bin Wu、J. David Warren、Jiehao Chen、Gong Chen、Zihao Hua、Samuel J. Danishefsky

  DOI：10.1016/j.tetlet.2006.04.132

  日期：2006.7

  Reiterative approaches in the fashioning of erythropoietin-directed, polyglycosylated polypeptides are disclosed. (c) 2006 Elsevier Ltd. All rights reserved.
• A Strategy for Probing the Autonomy of Cross-Domain Stereochemical Communication in Glycoconjugates
  作者：David H. Live、Zhi-Guang Wang、Ulrich Iserloh、Samuel J. Danishefsky

  DOI：10.1021/ol0070233

  日期：2001.3.1

  [GRAPHICS]Glycoproteins contain carbohydrate and peptide sectors. As a model for studying whether there exists stereochemical "communication" between the two domains, we prepared two glycopeptides differing only in the absolute stereochemistry of the peptide domain (L-peptide vs D-peptide), High-field NMR spectroscopy revealed that there are distinct and measurable differences, indicating that the two domains are at some level interactive.