L-O-valine-L-valine | 112757-20-7

• 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: L-O-valine-L-valine
• 英文别名: L-O-Val-L-Val；(2S)-2-[[(2S)-2-hydroxy-3-methylbutanoyl]amino]-3-methylbutanoic acid
• CAS: 112757-20-7
• 化学式: C₁₀H₁₉NO₄
• 分子量: 217.265
• InChiKey: AMBDHXBXGARDLW-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-O-valine-L-valine 、 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,4S,5S)-4-hydroxy-5-[[(2S)-2-[[(2S)-2-hydroxy-3-methylbutanoyl]amino]-3-methylbutanoyl]amino]-2-methyl-N-[(2S)-3-methyl-1-oxo-1-(pyridin-4-ylmethylamino)butan-2-yl]-6-phenylhexanamide
  参考文献：
  名称：

  P3 cap modified Phe*-Ala series BACE inhibitors

  摘要：

  With the aim of reducing molecular weight and adjusting log D value of BACE inhibitors to more favorable range for BBB penetration and better bioavailability, we synthesized and evaluated several series of P3 cap modified BACE inhibitors obtained via replacement of the P3 NHBoc moiety as seen in 3 with other polar functional groups such as amino, hydroxyl and fluorine. Several promising inhibitors emerging from this P3 cap SAR study (e.g., 15 and 19) demonstrated good enzyme inhibitory potencies (BACE-1 IC50 < 50 nM) and whole cell activities (IC50 similar to 1 muM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.085
• 作为产物：
  描述：

  L-缬氨酸甲酯 在 sodium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 L-O-valine-L-valine
  参考文献：
  名称：

  P3 cap modified Phe*-Ala series BACE inhibitors

  摘要：

  With the aim of reducing molecular weight and adjusting log D value of BACE inhibitors to more favorable range for BBB penetration and better bioavailability, we synthesized and evaluated several series of P3 cap modified BACE inhibitors obtained via replacement of the P3 NHBoc moiety as seen in 3 with other polar functional groups such as amino, hydroxyl and fluorine. Several promising inhibitors emerging from this P3 cap SAR study (e.g., 15 and 19) demonstrated good enzyme inhibitory potencies (BACE-1 IC50 < 50 nM) and whole cell activities (IC50 similar to 1 muM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.085

文献信息

• Structure Revision of Isocereulide A, an Isoform of the Food Poisoning Emetic Bacillus cereus Toxin Cereulide
  作者：Veronika Walser、Markus Kranzler、Monika Ehling-Schulz、Timo D. Stark、Thomas F. Hofmann

  DOI：10.3390/molecules26051360

  日期：——

  The emetic Bacillus cereus toxin cereulide presents an enormous safety hazard in the food industry, inducing emesis and nausea after the consumption of contaminated foods. Additional to cereulide itself, seven structurally related isoforms, namely the isocereulides A–G, have already been elucidated in their chemical structure and could further be identified in B. cereus contaminated food samples. The

  催吐的蜡状芽孢杆菌毒素蜡样内酯在食品工业中存在巨大的安全隐患，食用受污染的食品后会引起呕吐和恶心。除了蜡菊酯本身以外，已经阐明了七个结构相关的同工型，即异蜡菊酯A–G的化学结构，并且可以在被蜡样芽孢杆菌污染的食物样品中进一步鉴定。新进行的异胡芦巴苷A的分离首次允许生物合成生产的异胡芦巴苷的1D和2D-NMR光谱，揭示的结果与其化学结构中1 - O- Leu部分的先前假设相矛盾。通过进一步应用水解后二肽分析，氨基酸和通过UPLC-ESI-TOF-MS进行α-羟酸分析以及MS n测序，可以纠正先前报道的异胡芦巴素A的结构。代替迄今假定的l - O -Leu，可以在环状十二肽中验证一个l - O -Ile单元，从而将异鲸蜡内酯A的结构修改为[（d - O -Leu- d -Ala- 1 - O -Val- l -Val）2（d - O -Leu- d -Ala- l - O -Ile- l-Val）]。
• Higher Structure of Cereulide, an Emetic Toxin from<i>Bacillus cereus</i>, and Special Comparison with Valinomycin, an Antibiotic from<i>Streptomyces fulvissimus</i>
  作者：Arthit Makarasen、Kenji Yoza、Minoru Isobe

  DOI：10.1002/asia.200900011

  日期：2009.5.4

  to be confused: Cereulide is an emetic toxin produced by Bacillus cereus through an unusual non‐ribosomal peptide synthesis, whereas valinomycin, produced by Streptomyces fulvissimus, is a known antibiotic drug. Cereulide has a greater complexation ability with metal ions than valinomycin and also exhibits a K+‐ion‐selective ionophore property at lower concentrations than valinomycin.

  不要混淆：蜡菊酯是蜡状芽孢杆菌通过异常的非核糖体肽合成产生的催吐毒素，而由富链链霉菌产生的缬胺霉素是已知的抗生素药物。Cereulide与金属离子的络合能力比缬氨霉素大，并且在比Valinomycin更低的浓度下还具有K +离子选择性离子载体性质。