Fmoc-Met-Thr(ΨMe,Mepro)-OH | 1451181-13-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Fmoc-Met-Thr(ΨMe,Mepro)-OH
• 英文别名: Fmoc-L-Met-L-Thr[PSI(Me,Me)Pro]-OH；(4S,5R)-3-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanylbutanoyl]-2,2,5-trimethyl-1,3-oxazolidine-4-carboxylic acid
• CAS: 1451181-13-7
• 化学式: C₂₇H₃₂N₂O₆S
• 分子量: 512.627
• InChiKey: DFVLCGBCANQGFL-XARZLDAJSA-N

物化性质

• 沸点：
  743.0±60.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  FMOC-L-蛋氨酸五氟苯基酯 在 4-甲基苯磺酸吡啶 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 Fmoc-Met-Thr(ΨMe,Mepro)-OH
  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。
• 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.