p-tolyl 3,4,6-tri-O-benzyl-(2,5-difluorobenzoyl)-1-thio-α-D-mannopyranoside | 1451180-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 3,4,6-tri-O-benzyl-(2,5-difluorobenzoyl)-1-thio-α-D-mannopyranoside
• 英文别名: thioglycoside 22
• CAS: 1451180-98-5
• 化学式: C₄₁H₃₈F₂O₆S
• 分子量: 696.812
• InChiKey: GTLROHWKXJHSGS-HZOWMXINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  50.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  p-tolyl 3,4,6-tri-O-benzyl-(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 6.0h， 以94%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→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：

  2,5-二氟苯甲酰氯 、 p-tolyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 以88%的产率得到p-tolyl 3,4,6-tri-O-benzyl-(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

• V3 IMMUNOGENS
  申请人：DUKE UNIVERSITY

  公开号：US20160106827A1

  公开（公告）日：2016-04-21

  The present invention relates, in general, to human immunodeficiency virus (HIV), and, in particular, to a vaccine for HIV-1, comprising synthetic V3 glycopeptides, and to methods of making and using same.

  本发明涉及人类免疫缺陷病毒（HIV），特别是涉及一种HIV-1疫苗，包括合成的V3糖肽，并涉及其制备和使用方法。