N-乙酰基-D-天冬氨酸 | 128574-89-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 天冬氨酸类衍生物
• 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
• 中文名称: N-乙酰基-D-天冬氨酸
• 英文名称: (R)-N-acetylaspartic acid
• 英文别名: N-acetylaspartic acid；N-Ac-D-Asp；N-acetyl-D-aspartic acid；N-Acetyl-D-asparaginsaeure；N-acetyl-D-aspartic acid；(2R)-2-acetamidobutanedioic acid
• CAS: 128574-89-0
• 化学式: C₆H₉NO₅
• 分子量: 175.141
• InChiKey: OTCCIMWXFLJLIA-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-乙酰基-D-天冬氨酸 、 维生素A 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以50%的产率得到di[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenyl] 2-(acetylamino)succinate
  参考文献：
  名称：

  Efficacy validation of synthesized retinol derivatives In vitro: stability, toxicity, and activity

  摘要：

  Retinol (vitamin A) is used as an antiwrinkle agent in the cosmetics industry. However, its photo-instability makes it unsuitable for use in general cosmetic formulations. To improve the photo-stability of retinol, three derivatives (3, 4, and 5) were synthesized and their biological activities were analyzed. H-1 NMR and HPLC analysis indicated that derivatives 3 and 5 were much more stable than retinol under our sunlight exposure conditions. When human adult fibroblasts were treated, the IC50 of derivative 3 was 96 muM, which is similar to that of retinol, as determined by the MTT assay. Derivatives 4 and 5 were 2.5 and 8 times more toxic than retinol, respectively. At 1 muM treatment, like retinol, derivatives 3 and 4 were specifically active for RARalpha out of six retinoid receptors (RAR/RXRalpha, beta, gamma). Dose-dependent analysis confirmed that derivative 4 was as active as retinol and the other two derivatives were less active for RARalpha. The effect of our derivatives on the expression of collagenase, an indicator of wrinkle formation, was measured using the transient co-expression of c-Jun and RT-PCR in HaCaT cells. Collagenase promoter activity, which is increased by c-Jun expression, was reduced 42% by retinol treatment. The other derivatives inhibited collagenase promoter activity similarly. These results were further confirmed by RT-PCR analysis of the collagenase gene. Taken together, our results suggest that retinol derivative 3 is a promising antiwrinkle agent based on its higher photo-stability, lower RARalpha activity (possibly indicating reduced side effects), and similar effect on collagenase expression. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00334-1
• 作为产物：
  描述：

  D-天门冬氨酸 、 乙酸酐 生成 N-乙酰基-D-天冬氨酸
  参考文献：
  名称：

  Cobalt Ion Activation of Renal Acylase I

  摘要：

  DOI：

  10.1021/ja01599a030

文献信息

• PROCESS FOR THE RESOLUTION OF ZOPICLONE AND INTERMEDIATE COMPOUNDS
  申请人：Bleda David Fernandez

  公开号：US20090036681A1

  公开（公告）日：2009-02-05

  The present invention refers to a process for the resolution into one of its enantiomers of the racemate of compound of formula (I): which comprises separating said one of its enantiomers from a diastereoisomeric salt of formula (II), which is formed by reaction of the racemic mixture with an optically active acetylated amino acid of formula (III). The invention also refers to new intermediates which are useful to carry out the process of the invention.

  本发明涉及一种用于将化合物的外消旋体之一分离出来的方法，该化合物的分子式为（I）：其中包括将所述外消旋体之一与分子式为（II）的非对映异构盐分离，该盐是由外消旋混合物与分子式为（III）的光学活性乙酰化氨基酸反应形成的。该发明还涉及用于执行本发明方法的新中间体。
• Process for the resolution of zopiclone and intermediate compounds
  申请人：ESTEVE QUIMICA, S.A.

  公开号：EP2020403A1

  公开（公告）日：2009-02-04

  The present invention refers to a process for the resolution into one of its enantiomers of the racemate of compound of formula (I): which comprises separating said one of its enantiomers from a diastereoisomeric salt of formula (II), which is formed by reaction of the racemic mixture with an optically active acetylated amino acid of formula (III). The invention also refers to new intermediates which are useful to carry out the process of the invention.

  本发明涉及一种用于将化合物的外消旋体之一分离出来的过程，该化合物的结构式为(I)：其中包括将该外消旋体与结构式(II)的二对映异构盐分离出来，该二对映异构盐是由外消旋混合物与结构式(III)的光学活性乙酰化氨基酸反应形成的。该发明还涉及用于实施该发明过程的新中间体。
• [EN] PROCESS FOR THE RESOLUTION OF ZOPICLONE AND INTERMEDIATE COMPOUNDS<br/>[FR] PROCÉDÉ DE RÉSOLUTION DU ZOPICLONE ET DE COMPOSÉS INTERMÉDIAIRES
  申请人：ESTEVE QUIMICA SA

  公开号：WO2009016251A1

  公开（公告）日：2009-02-05

  The present invention refers to a process for the resolution into one of its enantiomers of the racemate of compound of formula (I): which comprises separating said one of its enantiomers from a diastereoisomeric salt of formula (II), which is formed by reaction of the racemic mixture with an optically active acetylated amino acid of formula (III). The invention also refers to new intermediates which are useful to carry out the process of the invention.

  本发明涉及一种将式(I)化合物的混合物的对映体分离成其中一种对映体的方法，包括从式(II)的非对映异构盐中分离出其中一种对映体，式(II)是由混合物与式(III)的光学活性乙酰化氨基酸反应而形成的。本发明还涉及用于执行本发明方法的新中间体。
• Acyl pseudodipeptides which carry a functionalised auxialiary arm
  申请人：——

  公开号：US20030203852A1

  公开（公告）日：2003-10-30

  The present invention is directed in particular to dipeptide-like compounds derived from functionally substituted amino acids, having fatty acid chains bound thereto through amidification of the amine functional groups of said dipeptide-like compounds, one end portion of which bears an accessory functional side chain spacer, with the other end portion being an acid group either in neutral or charged state. Compounds of the present invention have immunomodulating properties like adjuvants, In addition, compounds of the invention can be grafted on a given antigen in order to modulate or tune the immune response or can be equally grafted on a pharmaceutical carrier to enhance the therapeutic effect or targetting thereof. Accordingly, compounds of the invention find use in human and veterinary medicine both as immunogens and diagnostic tools.

  本发明特别针对从功能性取代的氨基酸衍生的二肽类化合物，其通过酰胺化作用将脂肪酸链结合到所述二肽类化合物的胺基官能团上，其中一端部分带有辅助功能侧链间隔物，另一端部分为酸基，可以是中性或带电状态。本发明化合物具有类似佐剂的免疫调节性质。此外，本发明化合物可以嫁接在给定的抗原上，以调节或调整免疫反应，也可以同样嫁接在药物载体上，以增强其治疗效果或靶向作用。因此，本发明化合物在人类和兽医学中均可用作免疫原和诊断工具。
• Novel acyl-dipeptide-like compounds bearing an accessory functional side chain spacer, a method for preparing the same and pharmaceutical compositions containing such products
  申请人：Bauer Jacques

  公开号：US20050192232A1

  公开（公告）日：2005-09-01

  The present invention is directed in particular to dipeptide-like compounds derived from functionally substituted amino acids, having fatty acid chains bound thereto through amidification of the amine functional groups of said dipeptide-like compounds, one end portion of which bears an accessory functional side chain spacer, with the other end portion being an acid group either in neutral or charged state. Compounds of the present invention have immunomodulating properties like adjuvants, In addition, compounds of the invention can be grafted on a given antigen in order to modulate or tune the immune response or can be equally grafted on a pharmaceutical carrier to enhance the therapeutic effect or targetting thereof. Accordingly, compounds of the invention find use in human and veterinary medicine both as immunogens and diagnostic tools.

  本发明特别涉及从功能取代氨基酸衍生的二肽类化合物，其通过酰胺化二肽类化合物的胺基官能团与脂肪酸链结合，其中一端部分带有辅助功能侧链间隔物，而另一端部分是中性或带电酸基团。本发明化合物具有像佐剂一样的免疫调节性质。此外，本发明化合物可以嫁接到给定的抗原上，以调节或调整免疫反应，或者可以同样嫁接到药物载体上，以增强治疗效果或定位作用。因此，本发明化合物在人类和兽医学中均可用作免疫原和诊断工具。