ethyl 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→3)-[3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→6)]-4-O-benzyl-2-O-(2,5-difluorobenzoyl)-1-thio-α-D-mannopyranoside | 1451181-05-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→3)-[3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→6)]-4-O-benzyl-2-O-(2,5-difluorobenzoyl)-1-thio-α-D-mannopyranoside
• 英文别名: Ethyl 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-alpha-D-mannopyranosyl-(1->3)-[3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-alpha-D-mannopyranosyl-(1->6)]-4-O-benzyl-2-O-(2,5-difluorobenzoyl)-1-thio-alpha-D-mannopyranoside；[(2S,3S,4S,5R,6R)-2-[[(2R,3R,4S,5S,6R)-5-(2,5-difluorobenzoyl)oxy-4-[(2R,3S,4S,5R,6R)-3-(2,5-difluorobenzoyl)oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-ethylsulfanyl-3-phenylmethoxyoxan-2-yl]methoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] 2,5-difluorobenzoate
• CAS: 1451181-05-7
• 化学式: C₉₀H₈₄F₆O₁₈S
• 分子量: 1599.7
• InChiKey: HSIWHDYWXVBEGR-PDLUUFHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.8
• 重原子数：
  115
• 可旋转键数：
  39
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  215
• 氢给体数：
  0
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  ethyl 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→3)-[3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→6)]-4-O-benzyl-2-O-(2,5-difluorobenzoyl)-1-thio-α-D-mannopyranoside 、 benzyl [3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→3)]-2-O-benzyl-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以75%的产率得到benzyl [3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→3)]-[[3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→3)]-[3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→6)]-4-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→6)]-2-O-benzyl-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-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
• 作为产物：
  描述：

  ethyl 4-O-benzyl-2-O-(2,5-difluorobenzoyl)-1-thio-α-D-mannopyranoside 、 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 以75%的产率得到ethyl 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→3)-[3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→6)]-4-O-benzyl-2-O-(2,5-difluorobenzoyl)-1-thio-α-D-mannopyranoside
  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

• SYNTHETIC ENV PROTEINS
  申请人：DUKE UNIVERSITY

  公开号：US20150283227A1

  公开（公告）日：2015-10-08

  The present invention relates, in general, to human immunodeficiency virus-1 (HIV-1), and, in particular to a vaccine for HIV-1 and to methods of making and using same. The present invention provides synthetic glycosylated HIV-1 peptides, method for their preparation and use.

  本发明涉及人类免疫缺陷病毒-1（HIV-1），特别涉及HIV-1疫苗及其制备和使用方法。本发明提供了人工合成的糖基化HIV-1肽，其制备和使用方法。