(2S,3S)-3-hydroxyglutamic acid | 6209-00-3

• 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: (2S,3S)-3-hydroxyglutamic acid
• 英文别名: (S)-3-hydroxy-L-glutamic acid；(2S,3S)-2-amino-3-hydroxypentanedioic acid
• CAS: 6209-00-3
• 化学式: C₅H₉NO₅
• 分子量: 163.13
• InChiKey: LKZIEAUIOCGXBY-OKKQSCSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-hydroxyglutamic acid 、 D-FDAA 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 生成 D-DAA-(2S,3S)-βOHGlu
  参考文献：
  名称：

  Aciculitin D，一种来自 Poecillastra sp. 的细胞毒性杂环肽。海绵

  摘要：

  从Poecillastra sp.中分离出一种新的环状脂肽 aciculitin D ( 1 )。在深海中收集的海绵。通过光谱分析和化学降解阐明了aciculitin D( 1 )的结构。就氨基酸序列而言，aciulitin D与aciulitin B的不同之处在于L-Gln对L-Thr的一个残基取代。然而，两种化合物之间某些残基的绝对构型不同。Aciculitin D ( 1 ) 对 HeLa 和 HCT-116 细胞具有细胞毒性，IC 50值分别为 4.5 μM 和 1.4 μM。

  DOI：

  10.1016/j.tet.2022.132859
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 (2S,3S)-3-hydroxyglutamic acid
  参考文献：
  名称：

  Kaneko et al., Nippon Kagaku Zasshi, 1959, vol. 80, p. 316,320

  摘要：

  DOI：

文献信息

• Synthesis of new β- and γ-benzyloxy-S-glutamic acid derivatives and evaluation of their activity as inhibitors of excitatory amino acid transporters
  作者：Lucia Tamborini、Paola Conti、Andrea Pinto、Simona Colleoni、Marco Gobbi、Carlo De Micheli

  DOI：10.1016/j.tet.2009.05.054

  日期：2009.8

  enantiomerically pure diasteroisomers of γ-benzyloxy-S-glutamic acid was performed using trans-4-hydroxy-l-proline as a source of chirality, while the erythro and threo isomers of β-benzyloxy-S-glutamic acid were prepared starting from (R)-Garner's aldehyde. All new derivatives were tested for their inhibitory activity against excitatory amino acid transporters in a rat synaptosomal preparation and their

  γ苄氧基的两个对映体纯非对映异构的有效立体选择性制备小号使用进行谷氨酸反式-4-羟基-升-脯氨酸作为手性源，而赤和苏β苄氧基的异构体小号-从（R）-加纳醛开始制备谷氨酸。测试了所有新衍生物在大鼠突触体制剂中对兴奋性氨基酸转运蛋白的抑制活性，并将其IC 50值与TBOA（一种通常用作谷氨酸转运蛋白的参考阻滞剂的低碳同系物）的IC 50值进行了比较。
• Synthesis of erythro-L-.BETA.-Hydroxyglutamic Acid Hydrochloride from L-Malic Acid.
  作者：Sojiro SHIOKAWA、Tomihisa OHTA、Shigeo NOZOE

  DOI：10.1248/cpb.40.1398

  日期：——

  Facile synthesis of erythro-L-β-hydroxyglutamic acid and its derivative, (2S, 3S)-3-acetoxypyroglutamate, from L-malimide is described. The Key reaction for the synthesis of 3-oxypyroglutamyl intermediate was the furylation of N-acylaminal acetate using zinc bromide-trimethylchlorosilane as an effective catalyst system. Oxidative cleavage of the furyl substituent afforded the 3-acetoxypyroglutamate, which on hydrolysis gave the title amino acid.

  本研究描述了从 L-丙二酰亚胺中简便合成红-L-β-羟基谷氨酸及其衍生物 (2S, 3S)-3-乙酰氧基焦谷氨酸的过程。合成 3-oxypyroglutamyl 中间体的关键反应是以溴化锌-三甲基氯硅烷为有效催化剂体系对 N-酰氨基乙酸酯进行呋喃化反应。呋喃基取代基的氧化裂解产生 3-乙酰氧基焦谷氨酸，水解后得到标题氨基酸。
• Facile Synthesis of 3‐Hydroxyglutamic Acids via Cyanation of Chiral <i>N</i>‐Acyliminium Cation Derived From (<i>S</i>)‐Malic Acid
  作者：Makoto Oba、Atsushi Mita、Yoshinori Kondo、Kozaburo Nishiyama

  DOI：10.1080/00397910500278446

  日期：2005.12

  (S)‐malic acid is described. The chiral cyclic imide derived from (S)‐malic acid was converted to an acetoxylactam by reduction with sodium borohydride followed by acetylation. The obtained acetoxylactam was treated with trimethylsilyl cyanide in the presence of boron trifluoride etherate to give the corresponding cyanolactam in high yield, even though the diastereoselectivity of the cyanation reaction was

  摘要描述了通过氰化衍生自 (S)-苹果酸的 N-acyliminium 中间体轻松合成 3-羟基谷氨酸。衍生自（S）-苹果酸的手性环状酰亚胺通过用硼氢化钠还原然后乙酰化转化为乙酰氧基内酰胺。所得乙酰氧基内酰胺在三氟化硼醚合物存在下用三甲基甲硅烷基氰化物处理以高产率得到相应的氰内酰胺，即使氰化反应的非对映选择性适中。氰内酰胺的非对映异构体可通过色谱分离并独立转化为 (2R,3S)- 和 (2S,3S)-3-羟基谷氨酸。
• Blaskovich, Mark A.; Lajoie, Gilles A., Journal of the American Chemical Society, 1993, vol. 115, # 12, p. 5021 - 5030
  作者：Blaskovich, Mark A.、Lajoie, Gilles A.

  DOI：——

  日期：——
• Kutznerides 1−4, Depsipeptides from the Actinomycete <i>Kutzneria</i> sp. 744 Inhabiting Mycorrhizal Roots of <i>Picea </i><i>a</i><i>bies</i> Seedlings
  作者：Anders Broberg、Audrius Menkis、Rimvydas Vasiliauskas

  DOI：10.1021/np050378g

  日期：2006.1.1

  Bioassay-guided fractionation of culture supernatants of the actinomycete Kutzneria sp. 744 resulted in the isolation of four new depsipeptides (1-4). Structure analysis revealed the general structure: cyclo[2-(I-methylcyclopropyl)-D-glycine-(2S,3aR,8aS)-6,7-dichloro-3a-hydroxy-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic acid-3-hydroxy-D-glutamic acid-o-methyl-L-serine-L-piperazie acid-(S)-2-hydroxy-3,3-dimethylbutanoic acid]. The 3-hydroxy-D-glutamic acid was present as its threo-isomer in 1 and 2 and as its erythro-isomer in 3 and 4. The piperazic acid was modified to its (R)-4-chloro analogue in 2 and to its C-5/N unsaturated analogue in 4. Compounds 1-4 displayed moderate spore germination inhibiting activity against several common root-rotting fungi.