1-dodecyl β-D-glucuronic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-dodecyl β-D-glucuronic acid
• 英文别名: (2S,3S,4S,5R,6R)-6-dodecoxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₁₈H₃₄O₇
• 分子量: 362.464
• InChiKey: HBVSTUNXDQLMAH-RNGZQALNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 sodium hypochlorite 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 三氟化硼乙醚 、 sodium methylate 、 碳酸氢钠 、 potassium bromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 1-dodecyl β-D-glucuronic acid
  参考文献：
  名称：

  Thermotropic and lyotropic properties of long chain alkyl glycopyranosides

  摘要：

  As part of a series of papers, the influence of carbohydrate headgroups and aliphatic chains on the mesogenic properties of glycolipids was investigated. Alkyl glycosides with different types of aliphatic chains were synthesised. Neutral glycolipids were oxidized to their uronic acid derivatives, using the well established TEMPO-oxidation. For comparison a 6-deoxy-6-amino alkylglucopyranoside was synthesised. In addition, the thermotropic and lyotropic phase behaviour of the synthesised compounds were investigated. The thermotropism was characterised by polarising microscopy, the lyotropism by the contact preparation method. (C) 2003 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2003.09.007

文献信息

• PEPTIDE PHARMACEUTICALS FOR INSULIN RESISTANCE
  申请人：NESTOR John J.

  公开号：US20140349928A1

  公开（公告）日：2014-11-27

  Described herein are methods of syntheses and therapeutic uses of covalently modified peptides and/or proteins. The covalently modified peptides and/or proteins allow for improved pharmaceutical properties of peptide and protein-based therapeutics.

  本文描述了共价修饰肽和/或蛋白质的合成方法和治疗用途。共价修饰的肽和/或蛋白质可以提高基于肽和蛋白质的治疗药物的药理特性。
• IMPROVED PEPTIDE PHARMACEUTICALS
  申请人：EUMEDERIS PHARMACEUTICALS, INC.

  公开号：US20150307550A1

  公开（公告）日：2015-10-29

  Described herein are methods of syntheses and therapeutic uses of covalently modified peptides and/or proteins. The covalently modified peptides and/or proteins allow for improved pharmaceutical properties of peptide and protein-based therapeutics.

  本文描述了共价修饰肽和/或蛋白质的合成方法和治疗用途。共价修饰的肽和/或蛋白质可以改善基于肽和蛋白质的治疗药物的药理特性。
• [EN] IMPROVED PEPTIDE PHARMACEUTICALS FOR TREATMENT OF NASH AND OTHER DISORDERS<br/>[FR] COMPOSÉS PHARMACEUTIQUES PEPTIDIQUES AMÉLIORÉS UTILISÉS POUR LE TRAITEMENT D'UNE STÉATOHÉPATITE NON ALCOOLIQUE ET D'AUTRES TROUBLES
  申请人：SPITFIRE PHARMA INC

  公开号：WO2019136158A1

  公开（公告）日：2019-07-11

  The disclosure provides peptide products comprising a peptide covalently attached to a surfactant moiety which have improved properties, including increased duration of action and bioavailability. The peptide products are useful for treating insulin resistance, diabetes, obesity, metabolic syndrome and cardiovascular diseases, and conditions associated therewith, such as NASH and PCOS.

  该披露提供了包括肽共价连接到表面活性剂基团的肽产品，具有改善的特性，包括增加作用持续时间和生物利用度。这些肽产品可用于治疗胰岛素抵抗、糖尿病、肥胖、代谢综合征和心血管疾病，以及相关的疾病，如NASH和PCOS。
• [EN] IMPROVED PEPTIDE PHARMACEUTICALS FOR INSULIN RESISTANCE<br/>[FR] PRODUITS PHARMACEUTIQUES PEPTIDIQUES AMÉLIORÉS CONTRE L'INSULINORÉSISTANCE
  申请人：MEDERIS DIABETES LLC

  公开号：WO2015184177A1

  公开（公告）日：2015-12-03

  Described herein are methods of syntheses and therapeutic uses of covalently modified peptides and/or proteins. The covalently modified peptides and/or proteins allow for improved pharmaceutical properties of peptide and protein-based therapeutics.

  本文描述了合成和治疗用途的共价修饰肽和/或蛋白质的方法。这些共价修饰的肽和/或蛋白质可以改善基于肽和蛋白质的治疗药物的药理特性。
• Surfactant‐modified parathyroid hormone fragments with high potency and prolonged action: Structure‐informed design using glycolipid surfactant conjugation
  作者：John J. Nestor、Wei Wang

  DOI：10.1002/pep2.24225

  日期：2021.9

  illustrates ease of synthesis and conjugation, range of modulation of pharmacokinetic/pharmacodynamic behavior and acceptability in vivo of this approach. Proof of concept used parathyroid hormone and showed that an N-terminal fragment can be modified, informed by the parathyroid hormone receptor x-ray structure, to produce high potency, enhanced intrinsic efficacy and prolonged action in vivo. This suggests

  肽的药物特性（高效能和特异性低毒性）使它们成为一种有吸引力的治疗类别，但通常作用时间短和生物利用度低会限制它们的用途。在这里，我们开始评估一类新的肽修饰，糖脂表面活性剂缀合，旨在延长肽疗法的半衰期。这项工作说明了这种方法的合成和结合的容易性、药代动力学/药效学行为的调节范围和体内可接受性。概念证明使用甲状旁腺激素，并表明可以根据甲状旁腺激素受体 X 射线结构对 N 末端片段进行修饰，以产生高效力、增强内在功效和延长体内作用. 这表明每天（甲状旁腺功能减退症）或每周（骨质疏松症）给药，并在整个星期内产生生物后遗症（干细胞成熟为成骨细胞）。选择化合物7进行高级研究。正在探索糖脂表面活性剂修饰肽的物理特性和开发潜力，并使用其他肽疗法。