2-((2R,3R,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)pyrrolidin-1-yl)acetic acid

• 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: 2-((2R,3R,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)pyrrolidin-1-yl)acetic acid
• 英文别名: N-carboxymethyl-2,5-dideoxy-2,5-imino-D-mannitol；2-[(2R,3R,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)pyrrolidin-1-yl]acetic acid
• 化学式: C₈H₁₅NO₆
• 分子量: 221.21
• InChiKey: SUEPCGFHWYZVMX-SJNFNFGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  122
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  草酸醛 、 Alpha-葡萄糖苷酶 在 水 作用下， 以100%的产率得到2-((2R,3R,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)pyrrolidin-1-yl)acetic acid
  参考文献：
  名称：

  从甜叶菊甜叶菊中分离出一种新型亚氨基糖氨基酸DMDP乙酸：甘氨酸和β-丙氨酸吡咯烷氨基酸的合成和糖苷酶抑制谱。

  摘要：

  DMDP乙酸Ñ -carboxymethyl -2,5-二脱氧-2,5-亚氨基- d -mannitol] 5从甜叶菊是从亚氨基糖轴承的导出的第一分离的天然氨基酸ñ -烷基侧链; 从GCMS研究中可以清楚地看出，这种带有乙酸和丙酸的衍生物在包括桑,、Baphia和英国风铃草在内的多种植物中都很常见，但是它们很难纯化。未保护的吡咯烷亚氨基糖与乙二醛水溶液反应以非常高的产率得到相应的N-乙酸。既吡咯烷和哌啶亚氨基糖Michael加成和多羟基脯氨酸至叔丙烯酸丁酯给出相应的N-丙酸，其中β-丙氨酸的氨基被掺入杂环中。这些简单的合成方法可以鉴定植物提取物中的这类新氨基酸，并提供用于生物学评估的纯净样品。DMDP N-乙酸和丙酸是有效的α-半乳糖苷酶抑制剂，与之相比，DMDP可以有效抑制β-半乳糖苷酶。

  DOI：

  10.1007/s00726-019-02730-5

文献信息

• Treatment of energy utilization disease
  申请人：Vida Pharma Limited

  公开号：US10842784B2

  公开（公告）日：2020-11-24

  Described are compositions comprising imino sugar acids for the treatment of energy utilization disease (e.g. metabolic syndrome, including any disease or disorder associated therewith, for example central obesity, elevated levels of triglycerides and diabetes, including type 1 diabetes, type 2 diabetes and insulin resistance), processes for producing said compositions from various plant sources, together with various products, compounds, compositions, medical uses and methods based thereon.

  所描述的是包含亚氨基糖酸的组合物，用于治疗能量利用疾病（例如代谢综合征，包括与之相关的任何疾病或紊乱，例如中心性肥胖、甘油三酯水平升高和糖尿病，包括 1 型糖尿病、2 型糖尿病和胰岛素抵抗）；从各种植物来源生产所述组合物的工艺，以及基于此的各种产品、化合物、组合物、医疗用途和方法。
• TREATMENT OF ENERGY UTILIZATION DISEASE
  申请人：Summit Corporation Plc

  公开号：EP2257286B1

  公开（公告）日：2016-12-28
• Treatment of Energy Utilization Disease
  申请人：Nash Robert James

  公开号：US20110015226A1

  公开（公告）日：2011-01-20

  Described are compositions comprising imino sugar acids for the treatment of energy utilization disease (e.g. metabolic syndrome, including any disease or disorder associated therewith, for example central obesity, elevated levels of triglycerides and diabetes, including type 1 diabetes, type 2 diabetes and insulin resistance), processes for producing said compositions from various plant sources, together with various products, compounds, compositions, medical uses and methods based thereon.
• [EN] TREATMENT OF ENERGY UTILIZATION DISEASE<br/>[FR] TRAITEMENT D'UNE MALADIE DE L'UTILISATION D'ÉNERGIE
  申请人：SUMMIT CORP PLC

  公开号：WO2009103953A1

  公开（公告）日：2009-08-27

  Described are compositions comprising imino sugar acids for the treatment of energy utilization disease (e.g. metabolic syndrome, including any disease or disorder associated therewith, for example central obesity, elevated levels of triglycerides and diabetes, including type 1 diabetes, type 2 diabetes and insulin resistance), processes for producing said compositions from various plant sources, together with various products, compounds, compositions, medical uses and methods based thereon.
• Isolation from Stevia rebaudiana of DMDP acetic acid, a novel iminosugar amino acid: synthesis and glycosidase inhibition profile of glycine and β-alanine pyrrolidine amino acids
  作者：R. Fernando Martínez、Sarah F. Jenkinson、Shinpei Nakagawa、Atsushi Kato、Mark R. Wormald、George W. J. Fleet、Jackie Hollinshead、Robert J. Nash

  DOI：10.1007/s00726-019-02730-5

  日期：2019.7

  the corresponding N-acetic acids in very high yield; Michael addition of both pyrrolidine and piperidine iminosugars and that of polyhydroxylated prolines to tert-butyl acrylate give the corresponding N-propionic acids in which the amino group of β-alanine is incorporated into the heterocyclic ring. These easy syntheses allow the identification of this new class of amino acid in plant extracts and provide

  DMDP乙酸Ñ -carboxymethyl -2,5-二脱氧-2,5-亚氨基- d -mannitol] 5从甜叶菊是从亚氨基糖轴承的导出的第一分离的天然氨基酸ñ -烷基侧链; 从GCMS研究中可以清楚地看出，这种带有乙酸和丙酸的衍生物在包括桑,、Baphia和英国风铃草在内的多种植物中都很常见，但是它们很难纯化。未保护的吡咯烷亚氨基糖与乙二醛水溶液反应以非常高的产率得到相应的N-乙酸。既吡咯烷和哌啶亚氨基糖Michael加成和多羟基脯氨酸至叔丙烯酸丁酯给出相应的N-丙酸，其中β-丙氨酸的氨基被掺入杂环中。这些简单的合成方法可以鉴定植物提取物中的这类新氨基酸，并提供用于生物学评估的纯净样品。DMDP N-乙酸和丙酸是有效的α-半乳糖苷酶抑制剂，与之相比，DMDP可以有效抑制β-半乳糖苷酶。