2-acetamido-2-deoxy-6-O-octanoyl-α-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-2-deoxy-6-O-octanoyl-α-D-glucopyranose
• 英文别名: 2-acetamide-2-deoxy-6-O-octanoyl-α-D-glucopyranose；2-acetamido-2-deoxy-6-O-octanoyl-alpha-D-glucopyranose；[(2R,3S,4R,5R,6S)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methyl octanoate
• 化学式: C₁₆H₂₉NO₇
• 分子量: 347.409
• InChiKey: NBIOTOPSRGCMBM-BTAUDXDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-octanoyl-α-D-glucopyranose 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 2-acetamido-2-deoxy-6-O-octanoyl-α-D-glucopyranose
  参考文献：
  名称：

  Synthesis and Properties of Surfactants derived fromN‐Acetyl‐D‐Glucosamine

  摘要：

  The synthesis of 2-acetamido-2-deoxy-6-O-octanoyl-D-glucono-1,5-lactone 9 and 2-acetamido-2-deoxy-6-O-octanoyl-alpha-D-glueopyranose 7 from 2-acetamido-2-deoxy-alpha-D-glucopyranose is reported. For both targets, the key intermediate was allyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-octanoyl-alpha-D-glucopyranoside 5. Surface tension measurements (critical micellar concentration of 22.3 mM and 5 mM for 9 and 7, respectively) showed up the surface activity of both compounds, while enzyme inhibition assays indicated that 9 could inhibit bovine beta-N-acetylglucosaminidase (K-i = 6.5 mu M) but not Serratia marcescens chitobiase nor hen egg-white lysozyme. Moreover, 7 was shown to induce chitinase production of S. marcescens and to be readily metabolized by these bacteria.[GRAPHICS]

  DOI：

  10.1080/07328300701634804

文献信息

• One-step synthesis of carbohydrate esters as antibacterial and antifungal agents
  作者：Madher N. AlFindee、Qian Zhang、Yagya Prasad Subedi、Jaya P. Shrestha、Yukie Kawasaki、Michelle Grilley、Jon Y. Takemoto、Cheng-Wei Tom Chang

  DOI：10.1016/j.bmc.2017.12.038

  日期：2018.2

  compounds were active against a panel of bacteria and fungi, including Staphylococcus aureus, methicillin-resistant S. aureus (MRSA), Candida albicans, Cryptococcus neoformans, Aspergillus flavus and Fusarium graminearum. Unlike prior studies on carbohydrate esters that focus only on antibacterial applications, our compounds are found to be active against both bacteria and fungi. Furthermore, the synthetic

  碳水化合物酯是可生物降解的，降解的加合物是天然存在的碳水化合物和脂肪酸，对环境无害，对人体无毒。已经开发出单碳水化合物的简单的一步区域选择性酰化，其导致了多种碳水化合物酯的合成。这些酰化碳水化合物的筛选表明，几种化合物对一组细菌和真菌具有活性，包括金黄色葡萄球菌，耐甲氧西林金黄色葡萄球菌（MRSA），白色念珠菌，新型隐球菌，黄曲霉和禾谷镰刀菌。。与先前对仅专注于抗菌应用的碳水化合物酯的研究不同，我们的化合物被发现对细菌和真菌均具有活性。此外，合成方法学适合于扩大各种酰化碳水化合物的生产。鉴定出的先导化合物MAN014可以在食品加工和防腐等应用中用作抗菌剂，并用于治疗动植物的细菌和真菌疾病。
• N-acetylglucosamine derivatives and use thereof
  申请人：Miura Kyoko

  公开号：US20060020127A1

  公开（公告）日：2006-01-26

  The present invention relates to An N-acetylglucosamine derivative represented by the following formula (1), and a hyaluronic acid production promoting agent containing the same and a skin external preparation containing the same: wherein R 1 is a hydrogen atom or an alkyl group having 2 to 18 carbon atoms; R 2 , R 3 , and R 4 are hydrogen atoms or acyl groups having 2 to 18 carbon atoms and may be all the same or different from others; the steric structure at position 1 may be α or β; provided that R 1 , R 2 , R 3 , and R 4 must not be all hydrogen atoms. It is intended to provide an easily available hyaluronic acid production promoting agent and a skin external preparation whereby the production of hyaluronic acid can be promoted in the skin and thus the skin can be maintained in a vital and moist state so that it is expected that the human skin can be prevented from age.

  本发明涉及一种由以下式（1）表示的N-乙酰葡萄糖氨衍生物，以及含有该衍生物的透明质酸生产促进剂和皮肤外用制剂：其中R1是氢原子或具有2到18个碳原子的烷基；R2、R3和R4是氢原子或具有2到18个碳原子的酰基，可以全部相同或不同；位置1处的立体结构可以是α或β；前提是R1、R2、R3和R4不能全部是氢原子。本发明旨在提供一种容易获得的透明质酸生产促进剂和皮肤外用制剂，从而可以促进皮肤中透明质酸的产生，使皮肤保持活力和湿润状态，从而预防人类皮肤老化。
• N-ACETYGLUCOSAMINE DERIVATIVES AND USE THEREOF
  申请人：MIURA Kyoko

  公开号：US20080293673A1

  公开（公告）日：2008-11-27

  The present invention relates to An N-acetylglucosamine derivative represented by the following formula (1), and a hyaluronic acid production promoting agent containing the same and a skin external preparation containing the same: wherein R 1 is a hydrogen atom or an alkyl group having 2 to 18 carbon atoms; R 2 , R 3 , and R 4 are hydrogen atoms or acyl groups having 2 to 18 carbon atoms and may be all the same or different from others; the steric structure at position 1 may be α or β; provided that R 1 , R 2 , R 3 , and R 4 must not be all hydrogen atoms. It is intended to provide an easily available hyaluronic acid production promoting agent and a skin external preparation whereby the production of hyaluronic acid can be promoted in the skin and thus the skin can be maintained in a vital and moist state so that it is expected that the human skin can be prevented from age.

  本发明涉及以下式（1）所表示的N-乙酰葡萄糖氨衍生物，以及含有该衍生物的透明质酸生产促进剂和皮肤外用制剂：其中，R1是氢原子或具有2至18个碳原子的烷基；R2、R3和R4是氢原子或具有2至18个碳原子的酰基，可以全部相同或不同；位置1的立体结构可以是α或β；前提是R1、R2、R3和R4不能全部是氢原子。旨在提供一种易于获得的透明质酸生产促进剂和皮肤外用制剂，通过促进皮肤中透明质酸的产生，从而使皮肤保持活力和湿润状态，预防人体皮肤老化。
• N-ACETYLGLUCOSAMINE DERIVATIVES AND USE THEREOF
  申请人：KAO CORPORATION

  公开号：EP1553101B1

  公开（公告）日：2016-11-30
• EP1712219
  申请人：——

  公开号：——

  公开（公告）日：——