2,5-dideoxy-2,5-imino-D-mannonic acid | 1225455-72-0

• 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: 2,5-dideoxy-2,5-imino-D-mannonic acid
• 英文别名: (3S)-3-hydroxy-bulgecinine；(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-L-proline；(3R)-3-hydroxy-L-bulgecinine；[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)proline]；(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-1-ium-2-carboxylate
• CAS: 1225455-72-0
• 化学式: C₆H₁₁NO₅
• 分子量: 177.157
• InChiKey: OGDAGJPNPKUXMD-KKQCNMDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-dideoxy-2,5-imino-D-mannonic acid 在 三乙胺 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 96.0h， 生成 N-(2-carboxyethyl)-2,5-dideoxy-2,5-imino-D-mannonic 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
• 作为产物：
  描述：

  (1R,4S,6R,7R)-7-phenylmethoxy-6-(phenylmethoxymethyl)-2-oxa-5-azabicyclo[2.2.1]heptan-3-one 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 ammonium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 16.0h， 以119 mg的产率得到2,5-dideoxy-2,5-imino-D-mannonic acid
  参考文献：
  名称：

  Looking glass inhibitors: scalable syntheses of DNJ, DMDP, and (3R)-3-hydroxy-l-bulgecinine from d-glucuronolactone and of l-DNJ, l-DMDP, and (3S)-3-hydroxy-d-bulgecinine from l-glucuronolactone. DMDP inhibits β-glucosidases and β-galactosidases whereas l-DMDP is a potent and specific inhibitor of α-glucosidases

  摘要：

  A convenient large-scale synthesis of 1-deoxynojirimyin (DNJ) from D-glucuronolactone involves introduction of azide at C-5 with retention of configuration to give 5-azido-5-deoxy-1,2-O-isopropylidene-alpha-D-glucofuranose as a key intermediate in an overall yield of up to 72%; the same intermediate can be transformed into DMDP (2R,3R,4R,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol] and (3R)-3-hydroxy-L-bulgecinine [(2S,3R,4R,5R)-3,4-dihydroxy-5-hydroxymethyl-L-proline]. L-Glucuronolactone, a readily available L-sugar chiron, may similarly be used to access the enantiomers L-DNJ, L-DMDP, and (3S)-3-hydroxy-D-bulgecinine. A comparison of glycosidase inhibition by DMDP (an inhibitor of beta-glucosidases and beta-galactosidases) and L-DMDP (a potent and specific alpha-glucosidase inhibitor) with the corresponding enantiomeric hydroxybulgecinines is reported; DMDP and (3R)-3-hydroxy-L-bulgecinine show weak inhibition of glycogen phosphorylase. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.017

文献信息

• Looking glass inhibitors: scalable syntheses of DNJ, DMDP, and (3R)-3-hydroxy-l-bulgecinine from d-glucuronolactone and of l-DNJ, l-DMDP, and (3S)-3-hydroxy-d-bulgecinine from l-glucuronolactone. DMDP inhibits β-glucosidases and β-galactosidases whereas l-DMDP is a potent and specific inhibitor of α-glucosidases
  作者：Daniel Best、Chen Wang、Alexander C. Weymouth-Wilson、Robert A. Clarkson、Francis X. Wilson、Robert J. Nash、Saori Miyauchi、Atsushi Kato、George W.J. Fleet

  DOI：10.1016/j.tetasy.2010.01.017

  日期：2010.3

  A convenient large-scale synthesis of 1-deoxynojirimyin (DNJ) from D-glucuronolactone involves introduction of azide at C-5 with retention of configuration to give 5-azido-5-deoxy-1,2-O-isopropylidene-alpha-D-glucofuranose as a key intermediate in an overall yield of up to 72%; the same intermediate can be transformed into DMDP (2R,3R,4R,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol] and (3R)-3-hydroxy-L-bulgecinine [(2S,3R,4R,5R)-3,4-dihydroxy-5-hydroxymethyl-L-proline]. L-Glucuronolactone, a readily available L-sugar chiron, may similarly be used to access the enantiomers L-DNJ, L-DMDP, and (3S)-3-hydroxy-D-bulgecinine. A comparison of glycosidase inhibition by DMDP (an inhibitor of beta-glucosidases and beta-galactosidases) and L-DMDP (a potent and specific alpha-glucosidase inhibitor) with the corresponding enantiomeric hydroxybulgecinines is reported; DMDP and (3R)-3-hydroxy-L-bulgecinine show weak inhibition of glycogen phosphorylase. (C) 2010 Elsevier Ltd. All rights reserved.
• 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。