N-decanoyl-L-methionine | 51570-51-5

• 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-decanoyl-L-methionine
• 英文别名: N-decanoyl-L-Met；(2S)-2-(decanoylamino)-4-methylsulfanyl-butanoic acid；(2S)-2-(decanoylamino)-4-methylsulfanylbutanoic acid
• CAS: 51570-51-5
• 化学式: C₁₅H₂₉NO₃S
• 分子量: 303.466
• InChiKey: PECAWSDTQIFOPF-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-decanoyl-L-methionine 在 recombinant Streptomyces mobaraensis aminoacylase 、 水 作用下， 生成 L-蛋氨酸
  参考文献：
  名称：

  Purification, Characterization, Molecular Cloning, and Expression of a New Aminoacylase fromStreptomyces mobaraensisThat Can HydrolyzeN-(Middle/Long)-chain-fatty-acyl-L-amino Acids as Well asN-Short-chain-acyl-L-amino acids

  摘要：

  我们在此报告了一种新的氨酰酶的纯化、特征化、分子克隆和表达，该酶最初从放线菌Mobaraensis（Sm-AA）的上清液中分离出来。纯化的野生型Sm-AA被发现是单体蛋白，分子量为55 kDa。克隆的Sm-AA基因包含一个1,383 bp的开放阅读框（ORF），编码460个氨基酸的多肽。BLAST搜索显示，Sm-AA属于肽酶M20家族，与来自Streptomyces pristinaespiralis的假设蛋白、来自Streptomyces avermitilis的假定肽酶、来自Frankia sp.的肽酶M20、来自流感嗜血杆菌的琥珀酰二氨基庚酸去琥珀酰酶，以及来自猪肾的氨酰酶-1的同源性分别为89%、88%、67%、29%和25%。Sm-AA基因被亚克隆入表达载体pSH19，并在Streptomyces lividans TK24中表达。重组Sm-AA在S. lividans细胞中的表达量约为S. mobaraensis上清液中Sm-AA的42倍。Sm-AA对各种N-乙酰-l-氨基酸和N-(中/长)-链脂肪酰-l-氨基酸表现出高水解活性，特别偏好l-Met、l-Ala、l-Cys等的酰基衍生物，其最佳反应pH和温度约为7.5和50°C（在pH 7.5下）。

  DOI：

  10.1271/bbb.90081
• 作为产物：
  描述：

  methyl (2S)-2-(decanoylamino)-4-methylsulfanylbutanoate 在 sodium hydroxide 作用下， 生成 N-decanoyl-L-methionine
  参考文献：
  名称：

  Synthesis and evaluation of anti-tumor activities of N4 fatty acyl amino acid derivatives of 1-β-arabinofuranosylcytosine

  摘要：

  1-beta-D-Arabinofuranosylcytosine (Ara-C, Cytarabine) is one of the drugs used for acute nonlympbocytic leukemia (ANLL). However, the bioavailability of Ara-C is relatively low due to its low lipophilicity. In order to improve the lipophilicity and bioavailability of Ara-C, a series of N-4 derivatives of Ara-C, i.e., (fatty acid)-(amino acid)-Ara-C analogues, were prepared. The 15 derivatives synthesized were characterized by their melting points, optical rotations and partition coefficients. It was found that the Ara-C derivatives synthesized in this study were more lipophilic than Ara-C as determined by their partition coefficients. Their in vitro cytotoxicity and in vivo anti-tumor activity were determined and compared with that of Ara-C. It was found that the derivatives were more active than Ara-C in Hela cells, but not in HL-60 cells. The in vivo results showed that some of the derivatives were more effective than Ara-C in mice bearing S-180 tumor while others showed a decreased activity in comparison with Ara-C. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.02.028

文献信息

• Pharmaceutical formulations for the oral delivery of peptide or protein drugs
  申请人：Cyprumed GmbH

  公开号：EP3006045A1

  公开（公告）日：2016-04-13

  The present invention relates to improved pharmaceutical formulations, uses and methods for the oral delivery of peptide or protein drugs with advantageously high bioavailability, safety and cost-effectiveness. In particular, the invention provides a peptide or protein drug having a molecular weight of equal to or less than about 50 kDa for use as a medicament, wherein said peptide or protein drug is to be administered orally in combination with a pharmaceutically acceptable copper salt/complex and/or a pharmaceutically acceptable zinc salt/complex, and with a pharmaceutically acceptable reducing agent. The invention also provides a pharmaceutical composition comprising: a peptide or protein drug having a molecular weight of equal to or less than about 50 kDa; a pharmaceutically acceptable copper salt/complex and/or a pharmaceutically acceptable zinc salt/complex; and a pharmaceutically acceptable reducing agent.

  本发明涉及肽或蛋白质药物口服给药的改进药物制剂、用途和方法，具有生物利用度高、安全性好和成本效益高等优点。特别是，本发明提供了一种分子量等于或小于约 50 kDa 的多肽或蛋白质药物，可用作药物，其中所述多肽或蛋白质药物将与药学上可接受的铜盐/络合物和/或药学上可接受的锌盐/络合物以及药学上可接受的还原剂一起口服给药。本发明还提供了一种药物组合物，其中包括：分子量等于或小于约 50 kDa 的多肽或蛋白药物；药学上可接受的铜盐/络合物和/或药学上可接受的锌盐/络合物；以及药学上可接受的还原剂。
• Fast-acting plant-based medicinal compounds and nutritional supplements
  申请人：RECEPTOR HOLDINGS, INC.

  公开号：US10588974B2

  公开（公告）日：2020-03-17

  Plant-based medicinal compounds or nutritional supplements in various carrier combinations are described. The carriers can include N-acylated fatty amino acids, penetration enhancers, and/or various other beneficial carriers. The plant-based composition/carrier combinations can create administration benefits.

  本文介绍了各种载体组合中的植物药用化合物或营养补充剂。载体可包括 N-酰化脂肪氨基酸、渗透促进剂和/或其他各种有益载体。植物性组合物/载体组合可带来用药益处。
• Pharmaceutical formulations for the oral delivery of peptide drugs
  申请人：Cyprumed GmbH

  公开号：US10905744B2

  公开（公告）日：2021-02-02

  The present invention relates to improved pharmaceutical formulations, uses and methods for the oral delivery of peptide drugs with advantageously high bioavailability, safety and costeffectiveness. In particular, the invention provides a peptide drug having a molecular weight of equal to or less than 5 kDa for use as a medicament, wherein said peptide drug is to be administered orally in combination with a pharmaceutically acceptable copper salt/complex and/or a pharmaceutically acceptable zinc salt/complex and/or a pharmaceutically acceptable iron salt/complex, and with a pharmaceutically acceptable complexing agent. The invention also provides a pharmaceutical composition comprising: a peptide drug having a molecular weight of equal to or less than 5 kDa; a pharmaceutically acceptable copper salt/complex and/or a pharmaceutically acceptable zinc salt/complex and/or a pharmaceutically acceptable iron salt/complex; and a pharmaceutically acceptable complexing agent.

  本发明涉及肽类药物口服给药的改进药物制剂、用途和方法，具有生物利用度高、安全和成本效益高等优点。特别是，本发明提供了一种分子量等于或小于 5 kDa 的多肽药物，可用作药物，其中所述多肽药物将与药学上可接受的铜盐/络合物和/或药学上可接受的锌盐/络合物和/或药学上可接受的铁盐/络合物以及药学上可接受的络合剂一起口服给药。本发明还提供了一种药物组合物，其中包括：分子量等于或小于 5 kDa 的多肽药物；药学上可接受的铜盐/络合物和/或药学上可接受的锌盐/络合物和/或药学上可接受的铁盐/络合物；以及药学上可接受的络合剂。
• Pharmaceutical compositions for delivery of peptide
  申请人：ANYA BIOPHARM INC.

  公开号：US11389474B2

  公开（公告）日：2022-07-19

  The present invention relates to a pharmaceutical composition including: a pharmaceutically effective amount of at least one peptide; and a pharmaceutically acceptable amount of a combination of: (a) at least one metal in form of any or a combination of a salt thereof and a complex thereof; and (b) at least one reducing agent, wherein, the at least one metal is selected from any or a combination of: vanadium, chromium and manganese, and wherein the combination of (a) at least one metal in form of any or a combination of a salt and a complex and (b) at least one reducing agent affords protection, at least in part, to the at least one peptide from proteolytic degradation upon ingestion thereof.

  本发明涉及一种药物组合物，包括：药学上有效量的至少一种肽；和药学上可接受量的以下物质的组合：(其中，至少一种金属选自钒、铬和锰中的任意一种或其组合，且(a)至少一种盐和络合物中的任意一种或其组合形式的金属和(b)至少一种还原剂的组合至少部分保护至少一种肽在摄入后不被蛋白水解降解。
• FATTY ACID ACYLATED AMINO ACIDS FOR ORAL PEPTIDE DELIVERY
  申请人：Novo Nordisk A/S

  公开号：EP2696847A1

  公开（公告）日：2014-02-19