3-ketodihydrosphingosine | 16105-69-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-ketodihydrosphingosine
• 英文别名: 3-dehydrosphinganine；(2S)-2-amino-1-hydroxyoctadecan-3-one
• CAS: 16105-69-4
• 化学式: C₁₈H₃₇NO₂
• 分子量: 299.497
• InChiKey: KBUNOSOGGAARKZ-KRWDZBQOSA-N

物化性质

• 沸点：
  438.6±30.0 °C(Predicted)
• 密度：
  0.923±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  3-ketodihydrosphingosine 在 ceramide synthase 、 3-ketodihydrosphingosine reductase 、 sphingolipids hydroxylase 作用下， 生成 Cer (t18:0/16:0)
  参考文献：
  名称：

  Convergent evolution of bacterial ceramide synthesis

  摘要：

  细菌域产生多种类型的神经酰胺，它们具有多种生理功能。在人类微生物组中，共生和致病细菌利用这些脂质来调节宿主的炎症系统。尽管它们的重要性日益增加，但它们的生物合成途径仍未明确，因为几种关键的真核生物神经酰胺合成酶在细菌中没有同源物。我们通过基因组和生化方法识别了六种蛋白质，完整构成了细菌神经酰胺合成的途径。生物信息学分析揭示了细菌神经酰胺合成的广泛潜力，从而使我们发现了一种能产生神经酰胺的革兰氏阳性菌。生化证据表明，细菌途径的运作顺序与真核生物的不同。此外，系统发育分析支持细菌和真核生物神经酰胺途径独立进化的假说。对细菌神经酰胺生物合成途径的阐明表明，它可能独立于真核生物途径进化，因为细菌缺乏许多真核生物酶的同源物，并且反应顺序不同。

  DOI：

  10.1038/s41589-021-00948-7
• 作为产物：
  描述：

  (2S)-2-(N-tert-butoxycarbonyl)amino-1-hydroxyoctadecan-3-one 在 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以19%的产率得到3-ketodihydrosphingosine
  参考文献：
  名称：

  Simplifungin and Valsafungins, Antifungal Antibiotics of Fungal Origin

  摘要：

  The targets of antifungal antibiotics in clinical use are more limited than those of antibacterial antibiotics. Therefore, new antifungal antibiotics with different mechanisms of action are desired. In the course of our screening for antifungal antibiotics of microbial origins, new antifungal antibiotics, simplifungin (1) and valsafungins A (2) and B (3), were isolated from cultures of the fungal strains Simplicillium minatense FKI-4981 and Valsaceae sp. FKH-53, respectively. The structures of 1 to 3 including their absolute stereochemistries were elucidated using various spectral analyses including NMR and collision-induced dissociation (CID)-MS/MS as well as chemical approaches including modifications to the Mosher's method. They were structurally related to myriocin. They inhibited the growth of yeast-like and zygomycetous fungi with MICs ranging between 0.125 and 8.0 mu g/mL. An examination of their mechanisms of action by the newly established assay using LC-MS revealed that 1 and 2 inhibited serine palmitoyltransferase activity, which is involved in sphingolipid biosynthesis, with IC50 values of 224 and 24 nM, respectively.

  DOI：

  10.1021/acs.joc.6b00952

文献信息

• Deoxynojirimycin analogues and their uses as glucosylceramidase inhibitors
  申请人：Academisch Ziekenhuis bij de Universiteit van Amsterdam

  公开号：EP1528056A1

  公开（公告）日：2005-05-04

  The invention provides a new class of deoxynojirimycin analogues, or pharmaceutically acceptable salts thereof which can suitably be used for the treatment of a disease selected from the group consisting of insulin resistance, Gauger disease, inflammatory diseases, hyperpigmentation and/or inflammatory skin conditions, overweight and obesity, lysosomal storage disorders, fungal diseases, melanoma and other tumors, and microbacterial infections. The invention further provides a pharmaceutical composition comprising said deoxynojirimycon analogue, or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

  该发明提供了一类新的脱氧诺吉霉素类似物，或其药学上可接受的盐，可用于治疗从胰岛素抵抗、高格氏病、炎症性疾病、多种病变和/或炎症性皮肤病变、超重和肥胖、溶酶体贮积疾病、真菌病、黑色素瘤和其他肿瘤，以及微生物感染等疾病中选择的疾病。该发明还提供了一种含有所述脱氧诺吉霉素类似物或其药学上可接受的盐以及药学上可接受的载体的药物组合物。
• [EN] GLYCOSPHINGOLIPIDS FOR USE IN MODULATING IMMUNE RESPONSES<br/>[FR] GLYCOSPHINGOLIPIDES UTILES À LA MODULATION DES RÉPONSES IMMUNITAIRES
  申请人：UNIV CALIFORNIA

  公开号：WO2013119857A1

  公开（公告）日：2013-08-15

  Provided herein are sphingolipid compounds that are useful for activating natural killer T cells. Also provided are methods for treating or preventing a disease or disorder that is treatable by activating the immune system by stimulating natural killer T cells. The compounds are therefore useful for treating or reducing the likelihood of occurrence of an immune diseases and disorders, such as autoimmune diseases or disorders. The compounds may also be used for treating or reducing the likelihood of occurrence of a microbial infection or for treating or reducing the likelihood of occurrence of a cancer in a subject by administering the sphingolipid compounds described herein.

  本文提供了可用于激活自然杀伤T细胞的鞘脂化合物。同时，还提供了通过刺激自然杀伤T细胞激活免疫系统来治疗或预防可治疗的疾病或疾病的方法。因此，这些化合物可用于治疗或减少免疫性疾病和疾病的发生可能性，如自身免疫性疾病或疾病。这些化合物也可用于通过给予所述鞘脂化合物来治疗或减少受试者微生物感染的可能性或治疗或减少受试者癌症发生的可能性。
• Compounds and methods for treating insulin resistance and cardiomyopathy
  申请人：Nestor John

  公开号：US20060079542A1

  公开（公告）日：2006-04-13

  Novel compounds, compositions comprising compounds, and methods for methods for preparing and using compounds are described herein. Methods of treating or ameliorating various conditions, including insulin resistance, pancreatic beta cell apoptosis, obesity, pro-thrombotic conditions, myocardial infarction, hypertension, dyslipidemia, manifestations of Syndrome X, congestive heart failure, inflammatory disease of the cardiovascular system, atherosclerosis, sepsis, type 1 diabetes, liver damage, and cachexia, by administering compounds described herein. Compounds presented herein may be used to modulate serine palmitoyl transferase activity.

  本文描述了新的化合物、包含这些化合物的组合物以及制备和使用这些化合物的方法。本文还描述了通过给予这些化合物治疗或改善各种病症的方法，包括胰岛素抵抗、胰岛β细胞凋亡、肥胖症、促凝血状态、心肌梗死、高血压、血脂异常、X综合征表现、充血性心力衰竭、心血管系统炎症性疾病、动脉粥样硬化、败血症、1型糖尿病、肝损伤和消瘦症。本文所述的化合物可以用于调节丝氨酸棕榈酰转移酶活性。
• [EN] DEOXYNOJIRIMYCIN ANALOGUES AND THEIR USES AS GLUCOSYLCERAMIDASE INHIBITORS<br/>[FR] ANALOGUES DE LA DESOXYNOJIRIMYCINE ET LEURS UTILISATIONS COMME INHIBITEURS DE LA GLUCOSYLCERAMIDASE
  申请人：AZ UNIV AMSTERDAM

  公开号：WO2005040118A1

  公开（公告）日：2005-05-06

  The invention provides a new class of deoxynojirimycin analogues, or pharmaceutically acceptable salts thereof which can suitably be used for the treatment of a disease selected from the group consisting of insulin resistance, Gauger disease, inflammatory diseases, hyperpigmentation and/or inflammatory skin conditions, overweight and obesity, lysosomal storage disorders, fungal diseases, melanoma and other tumors, and microbacterial infections. The invention further provides a pharmaceutical composition comprising said deoxynojirimycon analogue, or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

  本发明提供了一类新型的脱氧诺吉霉素类似物，或其药学上可接受的盐，可适用于治疗选自胰岛素抵抗、高加病、炎症性疾病、色素沉着和/或炎症性皮肤状况、超重和肥胖、溶酶体贮积症、真菌病、黑色素瘤和其他肿瘤、微生物感染的疾病。本发明还提供了一种包含所述脱氧诺吉霉素类似物或其药学上可接受的盐以及药学上可接受的载体的制药组合物。
• COMPOUNDS FOR AND METHODS OF TREATING INSULIN RESISTANCE AND INFLAMMATION
  申请人：Nestor John

  公开号：US20080096799A1

  公开（公告）日：2008-04-24

  Novel compounds, compositions comprising compounds, and methods for preparing and using compounds are described herein. Methods of treating or ameliorating various conditions, including insulin resistance, pancreatic beta cell apoptosis, obesity, pro-thrombotic conditions, myocardial infarction, hypertension, dyslipidemia, manifestations of Syndrome X, congestive heart failure, inflammatory disease of the cardiovascular system, atherosclerosis, restenosis, sepsis, type 1 diabetes, liver damage, COPD, emphysema and cachexia, by administering compounds described herein. Compounds presented herein may be used to modulate serine palmitoyl transferase activity.

  本文描述了新型化合物、包含化合物的组合物以及制备和使用化合物的方法。本文介绍了治疗或改善各种病症的方法，包括胰岛素抵抗、胰岛β细胞凋亡、肥胖症、促凝血状态、心肌梗死、高血压、血脂异常、X综合征表现、充血性心力衰竭、心血管系统炎症性疾病、动脉粥样硬化、再狭窄、败血症、1型糖尿病、肝损伤、慢性阻塞性肺疾病、肺气肿和消瘦，通过给予本文描述的化合物进行治疗。本文介绍的化合物可用于调节丝氨酸棕榈酰基转移酶活性。