D-glycero-D-guloheptonic acid | 504-91-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 赖氨酸类衍生物
• 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: D-glycero-D-guloheptonic acid
• 英文别名: δ-allo-hydroxylysine；DL-threo-5-hydroxy-lysine；(+/-)-threo-2,6-Diamino-5-hydroxy-hexansaeure；DL-threo-5-Hydroxy-lysin；(2R,5R)-2,6-diamino-5-hydroxyhexanoic acid
• CAS: 504-91-6；1190-94-9；3506-26-1；6000-08-4；18899-29-1；18899-30-4；18899-31-5；52153-41-0；78088-29-6
• 化学式: C₆H₁₄N₂O₃
• 分子量: 162.189
• InChiKey: YSMODUONRAFBET-RFZPGFLSSA-N

物化性质

• 沸点：
  416.2±45.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  D-glycero-D-guloheptonic acid 在 periodate 作用下， 生成 3,4-二氢-2H-吡咯-2-羧酸
  参考文献：
  名称：

  Synthesis and Evaluation of Effective Inhibitors of Plant δ¹-Pyrroline-5-carboxylate Reductase

  摘要：

  Analogues of previously studied phenyl-substituted aminomethylene-bisphosphonic acids were synthesized and evaluated as inhibitors of Arabidopsis thaliana delta(1)-pyrroline-5-carboxylate reductase. With the aim of improving their effectiveness, two main modifications were introduced into the inhibitory scaffold: the aminomethylenebisphosphonic moiety was replaced with a hydroxymethylenebisphosphonic group, and the length of the molecule was increased by replacing the methylene linker with an ethylidene chain. In addition, chlorine atoms in the phenyl ring were replaced with various other substituents. Most of the studied derivatives showed activity in the rnicromolar to millimolar range, with two of them being more effective than the lead compound, with concentrations inhibiting 50% of enzyme activity as low as 50 mu M. Experimental evidence supporting the ability of these inhibitors to interfere with proline synthesis in vivo is also shown.

  DOI：

  10.1021/jf401234s
• 作为产物：
  描述：

  [(3R,6S)-6-(Benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester 在 甲醇 、 钯 作用下， 生成 D-glycero-D-guloheptonic acid
  参考文献：
  名称：

  Zahn; Zuern, Chemische Berichte, 1958, vol. 91, p. 1359,1368

  摘要：

  DOI：

文献信息

• Design, synthesis and cytotoxicity of bengamide analogues and their epimers
  作者：Thi Dao Phi、Huong Doan Thi Mai、Van Hieu Tran、Bich Ngan Truong、Tuan Anh Tran、Van Loi Vu、Van Minh Chau、Van Cuong Pham

  DOI：10.1039/c6md00587j

  日期：——

  HL60, and Hela) demonstrated that the configuration of C-2′ seems to be critical for the cytotoxic activity of compounds 8b (2′R) and 8a (2′S). Additionally, comparison of cytotoxicity of the protected acetonide compounds with that of their corresponding deprotected bengamide analogues suggested that the flexibility of the ketide side chain should be required for their cytotoxic activity.

  从开始d -甘油基- d -庚-heptonic酸γ内酯和氨基酸，合成了一些非对映异构bengamide类似物。反应条件的优化表明，微波辐射辅助是制备氨基内酰胺以及内酯5与氨基内酰胺偶联反应的有力方法。针对六种癌细胞系（KB，HepG2，LU1，MCF7，HL60和Hela）的细胞毒活性评估表明，C-2'的构型似乎对于化合物8b（2'R）和8a（ 2 ′S）。另外，将被保护的丙酮化物与它们相应的去保护的苯甲酰胺类似物的细胞毒性进行比较表明，对于它们的细胞毒性活性，应要求酮化物侧链的柔韧性。
• Stereoselective Synthesis of (2R,5R)- and (2S,5R)-5-Hydroxylysine
  作者：Adrianus M. C. H. van den Nieuwendijk、Nicole M. A. J. Kriek、Johannes Brussee、Jacques H. van Boom、Arne van der Gen

  DOI：10.1002/1099-0690(200011)2000:22<3683::aid-ejoc3683>3.0.co;2-u

  日期：2000.11

  A stereoselective synthesis of (2S,5R)-5-hydroxylysine (1) and (2R,5R)-5-hydroxylysine (17), based on a concept involving Williams glycine template methodology and (R)-hydroxynitrile lyase for the introduction of chirality at the α-position and the side-chain, respectively, is described. This strategy offers an expeditious route towards orthogonally protected 5-hydroxylysines.

  （2 S，5 R）-5-羟基赖氨酸（1）和（2 R，5 R）-5-羟基赖氨酸（17）的立体选择性合成，基于涉及威廉姆斯甘氨酸模板法和（R）-羟基腈裂解酶的概念描述了分别在α位和侧链引入手性的方法。这种策略为正交保护的5-羟基赖氨酸提供了一条快捷途径。
• The 2-Oxoglutarate-Dependent Oxygenase JMJD6 Catalyses Oxidation of Lysine Residues to give 5S-Hydroxylysine Residues
  作者：Monica Mantri、Nikita D. Loik、Refaat B. Hamed、Timothy D. W. Claridge、James S. O. McCullagh、Christopher J. Schofield

  DOI：10.1002/cbic.201000641

  日期：2011.3.7

  Amino acid analyses reveal that JMJD6‐catalysed hydroxylation of RNA‐splicing regulatory protein fragments occurs to give hydroxylysine products with 5S stereochemistry. This contrasts with collagen lysyl hydroxylases, which give 5R‐hydroxylated products. The work suggests that more than one subfamily of lysyl hydroxylases has evolved and illustrates the importance of stereochemical assignments in

  氨基酸分析表明，JMJD6 催化的 RNA 剪接调节蛋白片段的羟基化产生具有 5 S立体化学的羟基赖氨酸产物。这与胶原蛋白赖氨酰羟化酶形成对比，后者产生 5 R-羟基化产物。这项工作表明，已经进化出不止一个赖氨酰羟化酶亚家族，并说明了立体化学分配在蛋白质组学分析中的重要性。
• Zahn; Zuern, Biochemische Zeitschrift, <hi>1958</hi>, vol. 330, p. 89,94
  作者：Zahn、Zuern

  DOI：——

  日期：——
• [EN] TEMPLATE-FIXED PEP TIDOMIME TICS WITH CXCR7 MODULATING ACTIVITY<br/>[FR] PEPTIDOMIMÉTIQUES FIXÉS AU BRIN MATRICE AYANT UNE ACTIVITÉ MODULATRICE DES CXCR7
  申请人：POLYPHOR AG

  公开号：WO2011095218A1

  公开（公告）日：2011-08-11

  Novel template-fixed β-hairpin peptidomimetics of the general formula (I) wherein the single elements T or P are α-amino acid residues connected from the carbonyl (C=O) point of attachment to the nitrogen (N) of the next element in clockwise direction and wherein said elements, depending on their positions in the chain, are defined in the description and the claims have the property to act on the receptor CXCR7. Thus, these β-hairpin peptidomimetics can be useful in the treatment or prevention of diseases or conditions in the area of dermatological disorders, metabolic diseases, inflammatory diseases, fibrotic diseases, infectious diseases, neurological diseases, cardiovascular diseases, respiratory diseases, gastro-intestinal tract disorders, urological diseases, ophthalmic diseases, stomatological diseases, haematological diseases and cancer; or the mobilisation of stem cells.