2-(S)-amino-3-(R)-hydroxy-6-carboxyhexanoic 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-(S)-amino-3-(R)-hydroxy-6-carboxyhexanoic acid
• 英文别名: (2S,3R)-2-amino-3-hydroxyhexanedioic acid
• 化学式: C₆H₁₁NO₅
• 分子量: 177.157
• InChiKey: AYIAXWLBJPKQAO-WUJLRWPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  琥珀半醛 、 聚甘氨酸 在 sodium hydroxide glycine hydroxymethyltransferase 、 磷酸吡哆醛 、 1,4-二巯基-2,3-丁二醇 作用下， 以 水 为溶剂， 反应 48.0h， 生成 2-(S)-amino-3-(R)-hydroxy-6-carboxyhexanoic acid 、 2-(S)-amino-3-(S)-hydroxy-6-carboxyhexanoic acid
  参考文献：
  名称：

  Enzymatic synthesis of ω-carboxy-β-hydroxy-(l)-α-amino acids

  摘要：

  Commercially available omega-carboxy-aldehydes and glycine have been subjected to the catalytic action of an L-threonine aldolase from Escherichia coli to give the corresponding beta-hydroxy-alpha-(L)-amino acids as a mixture of erythro/threo epimers.Specifically, the reaction with glyoxylic acid (2) gave the epimeric beta-hydroxy-(L)-aspartates (t,e)-9 that could be isolated by ion-exchange chromatography in 67% yield. Following esterification and N-Boc protection, the two epimers could be isolated as pure compounds.Similarly, the aldolase-catalyzed addition of glycine to succinic semialdehyde (4) gave the expected mixture of beta-hydroxy-L-alpha-aminoadipic acids (t)-12 and (e)-12 in 34% yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.070

文献信息

• Enantioselective Syntheses of 1-Carbacephalosporins from Chemoenzymically Derived β-Hydroxy-α-Amino Acids: Applications to the Total Synthesis of Carbacephem Antibiotic Loracarbef
  作者：Billy G Jackson、Steve W Pedersen、Jack W Fisher、Jerry W Misner、John P Gardner、Michael A Staszak、Christopher Doecke、John Rizzo、James Aikins、Eugene Farkas、Kristina L Trinkle、Jeffrey Vicenzi、Matt Reinhard、Eugene P Kroeff、Chris A Higginbotham、R.J Gazak、Tony Y Zhang

  DOI：10.1016/s0040-4020(00)00416-6

  日期：2000.7

  Serine hydroxymethyltransferase (SHMT) derived from recombinant E. coli was found to be able to catalyze the condensation between glycine and 4-pentenaldehyde, affording enantiopure l-erythro-2-amino-3-hydroxy-6-heptenoic acid (AHHA) in high yield and throughput. Conversion of this chiral intermediate of biosynthetic origin to the oral carbacephalosporin antibiotic loracarbef (Lorabid®) via β-lactam

  发现重组大肠杆菌衍生的丝氨酸羟甲基转移酶（SHMT）能够催化甘氨酸和4-戊醛之间的缩合，从而在高浓度下提供对映体纯的1-赤型-2-氨基-3-羟基-6-庚烯酸（AHHA）产量和吞吐量。此手性中间体的生物合成来源的转化为口服抗生素碳头孢菌素劳拉卡帕（Lorabid ®达到）通过β内酰胺形成反应和随后的环化迪克曼。
• L-THREONINE OVERPRODUCING MICROORGANISM AND METHOD FOR PREPARING L-THREONINE USING THE SAME
  申请人：Korea Advanced Institute of Science and Technology

  公开号：EP2121918B1

  公开（公告）日：2011-09-28