N-acetyl-nor-muramyl-L-alanyl-D-isoglutamine

• 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: N-acetyl-nor-muramyl-L-alanyl-D-isoglutamine
• 英文别名: (4R)-4-[[(2S)-2-[[2-[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxyacetyl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid
• 化学式: C₁₈H₃₀N₄O₁₁
• 分子量: 478.456
• InChiKey: KCUSRWLYTAYGAU-KQSQHPHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  247
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (4-nitrophenyl)methyl (4R)-4-[[(2S)-2-[[2-[[(4aR,6S,7R,8R,8aS)-7-acetamido-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]acetyl]amino]propanoyl]amino]-5-amino-5-oxopentanoate 生成 N-acetyl-nor-muramyl-L-alanyl-D-isoglutamine
  参考文献：
  名称：

  MISRA, PRAVIN K.;HAQ, WAHAJUL;KATTI, SETURAM B.;MATHUR, KRISHNA B., J. CHEM. RES. (S),(1988) N 11, C. 374-375

  摘要：

  DOI：

文献信息

• HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS
  申请人：Academia Sinica

  公开号：US20160102116A1

  公开（公告）日：2016-04-14

  Glycosphingolipids (GSLs) compositions and methods for iNKT-independent induction of chemokines are disclosed.

  糖脂类脂质（GSLs）的组成和诱导化学因子独立于iNKT的方法被揭示。
• HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS WITH ALTERED GLYCOSYL GROUPS
  申请人：Academia Sinica

  公开号：US20150071960A1

  公开（公告）日：2015-03-12

  Glycosphingolipids (GSLs) bearing α-glucose (α-Glc) that preferentially stimulate human invariant NKT (iNKT) cells are provided. GSLs with α-glucose (α-Glc) that exhibit stronger induction in humans (but weaker in mice) of cytokines and chemokines and expansion and/or activation of immune cells than those with α-galactose (α-Gal) are disclosed. GSLs bearing α-glucose (α-Glc) and derivatives of α-Glc with F at the 4 and/or 6 positions are provided. Methods for iNKT-independent induction of chemokines by the GSL with α-Glc and derivatives thereof are disclosed. Methods for immune stimulation in humans using GSLs with α-Glc and derivatives thereof are provided.

  提供了带有α-葡萄糖（α-Glc）的糖脂类物质（GSLs），这些物质优先刺激人类不变NKT（iNKT）细胞。公开了具有α-葡萄糖（α-Glc）的GSLs在人类（但在小鼠中较弱）中诱导细胞因子和趋化因子以及扩张和/或激活免疫细胞的能力强于具有α-半乳糖（α-Gal）的物质。提供了带有α-葡萄糖（α-Glc）和α-Glc在4和/或6位置带有F衍生物的GSLs。公开了使用带有α-Glc及其衍生物的GSL对趋化因子进行iNKT独立诱导的方法。提供了使用带有α-Glc及其衍生物的GSL在人类中进行免疫刺激的方法。
• [EN] ADJUVANT COMPOSITION AND METHODS FOR ITS USE<br/>[FR] COMPOSITION ADJUVANTE ET METHODES D'UTILISATION CORRESPONDANTES
  申请人：INNATE PHARMA

  公开号：WO2005102385A1

  公开（公告）日：2005-11-03

  The present invention is directed to a vaccine adjuvant which improves the vaccine potency. More specifically, the present invention is directed to the use of a ϜδT lymphocyte activator as vaccine adjuvant to promote and enhance antigen specific immunological responses, as well as a vaccine composition comprising a ϜδT lymphocyte activator.

  本发明涉及一种改善疫苗效力的疫苗佐剂。更具体地说，本发明涉及将ϜδT淋巴细胞激活剂用作疫苗佐剂，以促进和增强特定抗原的免疫反应，以及包含ϜδT淋巴细胞激活剂的疫苗组合物。
• Use of synthetic glycolipids as universal adjuvants for vaccines against cancer and infectious diseases
  申请人：Tsuji Moriya

  公开号：US20050192248A1

  公开（公告）日：2005-09-01

  The present invention relates to methods and compositions for augmenting an immunogenicity of an antigen in a mammal, comprising administering said antigen together with an adjuvant composition that includes a synthetic glycolipid compound of Formula I, as described herein. According to the present invention, the use of a compound of Formula I as an adjuvant is attributed at least in part to the enhancement and/or extension of antigen-specific Th1-type responses, in particular, CD8+ T cell responses. The methods and compositions of the present invention can be useful for prophylaxis and treatment of various infectious and neoplastic diseases.

  本发明涉及一种增强哺乳动物体内抗原免疫原性的方法和组合物，包括将所述抗原与包含本文所述的化学合成糖脂化合物 Formula I 的佐剂组合物一起给予。根据本发明，将 Formula I 化合物用作佐剂，至少部分归因于增强和/或延长特异性 Th1 类型反应，特别是 CD8+ T 细胞反应。本发明的方法和组合物可用于预防和治疗各种传染性和肿瘤性疾病。
• [EN] SAPONIN-BASED VACCINE ADJUVANTS<br/>[FR] ADJUVANTS DE VACCIN À BASE DE SAPONINES
  申请人：UAB RES FOUND

  公开号：WO2019183159A1

  公开（公告）日：2019-09-26

  Provided are variants of saponins that are found in Quillaja saponaria (QS) Molina tree bark that are chemically modified to distinguish them from naturally occurring parent saponins. The modified saponins have increased adjunctive activity compared to the unmodified parent saponins. Defined structures allow for comparisons of the modifying groups with respect to their respective adjunct activity and permit characterized vaccine formulations that have one or more defined saponins.

  提供了在Quillaja saponaria (QS) Molina树皮中发现的皂苷的变种，这些皂苷经过化学修饰，以使它们与自然存在的原始皂苷有所区别。经过修改的皂苷与未经修改的原始皂苷相比具有增强的辅助活性。定义的结构允许对修饰基团进行比较，以确定它们各自的辅助活性，并允许确定具有一个或多个定义的皂苷的疫苗配方。