threo-β-hydroxy-L-glutamic acid (threo-L-BHGA) | 6208-98-6

• 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: threo-β-hydroxy-L-glutamic acid (threo-L-BHGA)
• 英文别名: (2S,3R)-3-hydroxyglutamic acid；L-threo-β-hydroxyglutamic acid；threo-3-hydroxy-L-glutamic acid；L-threo-β-Hydroxy-Glutaminsaeure；L_S-thero-2-Amino-3-hydroxy-glutarsaeure；L_S-threo-3-Hydroxy-glutaminsaeure；L_S-threo-3-hydroxy-glutamic acid；(2S,3R)-2-amino-3-hydroxypentanedioic acid；threo-L-3-Hydroxy-glutaminsaeure
• CAS: 6208-98-6
• 化学式: C₅H₉NO₅
• 分子量: 163.13
• InChiKey: LKZIEAUIOCGXBY-FONMRSAGSA-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：

  threo-β-hydroxy-L-glutamic acid (threo-L-BHGA) 生成 (R)-(-)-4-氨基-3-羟基丁酸
  参考文献：
  名称：

  On the Absolute Configuration ofl-Carnitine (Vitamin B_T)

  摘要：

  DOI：

  10.1246/bcsj.35.1153
• 作为产物：
  描述：

  L-cis-3-Hydroxy-5-oxo-pyrrolidin-2-carbonsaeure 在 盐酸 作用下， 生成 threo-β-hydroxy-L-glutamic acid (threo-L-BHGA)
  参考文献：
  名称：

  Kamiya,T., Chemical and pharmaceutical bulletin, 1969, vol. 17, # 5, p. 890 - 894

  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。
• Structure and Biological Activity of Neopeptins A, B and C, Inhibitors of Fungal Cell Wall Glycan Synthesis
  作者：Makoto Ubukata、Masakasu Uramoto、Jun Uzawa、Kiyoshi Isono

  DOI：10.1080/00021369.1986.10867376

  日期：1986.2

  The antifungal antibiotics, neopetins A(1), B(2) and C(3), were found to be cyclic lipopeptides containing unusual amino acids, their structures being elucidated on the basis of chemical and spectroscopic evidence. They inhibited mannoprotein and β-1,3-glucan synthetases from Saccharomyces cerevisiae. The structure-biological activity relationship is discussed.

  抗真菌抗生素新宠素A（1）、B（2）和C（3）被发现是含有特殊氨基酸的环状脂肽，其结构基于化学和光谱证据进行阐明。它们抑制了来自酿酒酵母（Saccharomyces cerevisiae）的甘露蛋白和β-1,3-葡聚糖合成酶。讨论了结构与生物活性之间的关系。
• Stellettapeptins A and B, HIV-inhibitory cyclic depsipeptides from the marine sponge Stelletta sp.
  作者：Hee Jae Shin、Mohammad A. Rashid、Laura K. Cartner、Heidi R. Bokesch、Jennifer A. Wilson、James B. McMahon、Kirk R. Gustafson

  DOI：10.1016/j.tetlet.2015.05.058

  日期：2015.7

  Two new HIV-inhibitory depsipeptides, stellettapeptins A (1) and B (2), were isolated from an extract of the marine sponge Stelletta sp., collected from northwestern Australia. Structures of these cyclic nonribosomal peptides were elucidated on the basis of extensive NMR data analysis, and chemical degradation and derivatization studies. Stellettapeptins contain numerous nonproteinogenic amino acid

  从澳大利亚西北部收集的海洋海绵Stelletta sp。的提取物中分离出两种新的HIV抑制性十肽肽stellettapeptins A（1）和B（2）。这些环状非核糖体肽的结构在广泛的NMR数据分析，化学降解和衍生化研究的基础上得到阐明。Stellettapeptins包含许多非蛋白质氨基酸残基，它们是第一个据报道包含3-羟基-6,8-二甲基非-4-（Z）-烯酸部分的肽。化合物1和2可以有效抑制HIV 50 RF与EC 50对人T淋巴细胞的感染 值分别为23和27 nM。
• FR901469, a Novel Antifungal Antibiotic from an Unidentified Fungus No. 11243. III. Structure Determination.
  作者：AKIHIKO FUJIE、HIDEYUKI MURAMATSU、SEIJI YOSHIMURA、MICHIZANE HASHIMOTO、NOBUHARU SHIGEMATSU、SHIGEHIRO TAKASE

  DOI：10.7164/antibiotics.54.588

  日期：——

  A novel antifungal antibiotic, FR901469, was isolated from an unidentified fungus No. 11243. It is a water-soluble 40-membered macrocyclic lipopeptidolactone, consisting of D-Ala, L-Tyr, L-Val, trans-4OH-L-Pro, trans-3OH-L-Pro, threo-3OH-L-Gln, Gly, L-Orn, L-Thr, three residues of D-alloThr and a (3R)-hydroxypalmitic acid. Its structure, including absolute configurations, was unequivocally determined

  从未知的真菌编号11243中分离出一种新型的抗真菌抗生素FR901469。它是一种水溶性40元大环脂肽内酯，由D-Ala，L-Tyr，L-Val，trans-4OH-L-Pro组成，反式-3OH-L-Pro，苏式-3OH-L-Gln，Gly，L-Orn，L-Thr，D-alloThr的三个残基和（3R）-羟基棕榈酸。根据化学和光谱学证据，其结构（包括绝对构型）明确确定为1。
• Leanza; Pfister, Journal of Biological Chemistry, 1953, vol. 201, p. 377,380
  作者：Leanza、Pfister

  DOI：——

  日期：——