L-亮氨酰-L-谷氨酸 | 16364-31-1

• 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
• 中文名称: L-亮氨酰-L-谷氨酸
• 英文名称: N-L-leucyl-L-glutamic acid
• 英文别名: Leu-Glu；H-Leu-Glu-OH；(2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]pentanedioic acid
• CAS: 16364-31-1；38062-67-8
• 化学式: C₁₁H₂₀N₂O₅
• mdl: MFCD00037302
• 分子量: 260.29
• InChiKey: NFNVDJGXRFEYTK-YUMQZZPRSA-N

物化性质

• 沸点：
  517.3±50.0 °C(Predicted)
• 密度：
  1.28 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.727
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  L-亮氨酰-L-谷氨酸 在 2-萘酚 作用下， 生成 Cyclo-[Leu-Glu]
  参考文献：
  名称：

  Preparation of l-Leucyl-l-glutamic Acid Anhydride and its Behavior toward Proteinases

  摘要：

  DOI：

  10.1021/ja01235a012
• 作为产物：
  描述：

  谷氨酸二甲酯 在 水 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 L-亮氨酰-L-谷氨酸
  参考文献：
  名称：

  Self-assembling dipeptide-based nontoxic vesicles as carriers for drugs and other biologically important molecules

  摘要：

  自组装短肽提供了制造有用的纳米/微观结构的机会，这些结构在药物传递中有潜在应用。我们在此报告了自组装的水溶性合成两肽形成的多囊泡结构，这些两肽在C末端含有谷氨酸残基。这些囊泡结构在广泛的pH范围内（pH 2-12）稳定。然而，它们对钙离子敏感，导致这些囊泡破裂。有趣的是，这些囊泡不仅可以包裹抗癌药物和荧光染料，还能在存在钙离子的情况下释放它们。此外，这些多囊泡结构在细胞内有潜力携带生物重要分子，如环磷酸腺苷（cAMP），同时保持其生物功能完好。MTT细胞存活实验表明，这些囊泡几乎无毒。因此，这些肽囊泡可以作为生物相容性的递送载体，用于携带药物和其他生物活性分子。

  DOI：

  10.1039/c1ob05757j

文献信息

• Amino-acids and peptides. Part XXXIV. Anchimerically assisted coupling reactions: the use of 2-pyridyl thiolesters
  作者：K. Lloyd、G. T. Young

  DOI：10.1039/j39710002890

  日期：——

  presented of the use in peptide synthesis of esters for which aminolysis is assisted by a neighbouring group. 2-Pyridyl thiolesters of phthaloyl-, benzyloxycarbonyl-, and t-butoxycarbonyl-amino-acids are described, and it is shown that they condense very rapidly even with hindered amino-esters to give high yields of protected dipeptides. Phthaloyl-L-phenylalanine pyrimidin-2-yl thiolester is also described

  给出了在酯的肽合成中的应用的其他实例，其中酯的水解是由相邻基团辅助的。描述了邻苯二甲酰基-，苄氧基羰基-和叔丁氧基羰基-氨基酸的2-吡啶基硫代酯，并且显示它们即使与受阻的氨基酯也非常快速地缩合以得到高产率的受保护的二肽。还描述了邻苯二甲酰基-L-苯丙氨酸嘧啶-2-基巯基酯。当叔丁氧羰基-L-缬氨酸2-吡啶基硫代酯与L-缬氨酸甲酯缩合时，即使存在三乙胺，也未检测到外消旋作用。硫醇酯与醇缓慢反应，O-叔丁氧羰基甘氨酰乙醇酸乙酯和-DL乳酸盐是这样准备的。与通常的活性酯氨解反应的溶剂依赖性相反，当溶剂从二甲亚砜变为二甲基甲酰胺然后变为二恶烷或二恶烷时，叔丁氧基羰基-L-亮氨酸2-吡啶硫基酯与对茴香胺的缩合速率增加。乙酸乙酯。
• Methods and systems for determining autism spectrum disorder risk
  申请人：Laboratory Corporation of America Holdings

  公开号：US10041932B2

  公开（公告）日：2018-08-07

  In certain embodiments, the invention stems from the discovery that analysis of population distribution curves of metabolite levels in blood can be used to facilitate predicting risk of autism spectrum disorder (ASD) and/or to differentiate between ASD and non-ASD developmental delay (DD) in a subject. In certain aspects, information from assessment of the presence, absence, and/or direction (upper or lower) of a tail effect in a metabolite distribution curve is utilized to predict risk of ASD and/or to differentiate between ASD and DD.

  在某些实施方案中，本发明源于发现血液中代谢物水平的群体分布曲线分析可用于促进预测自闭症谱系障碍（ASD）的风险和/或区分受试者的自闭症谱系障碍和非自闭症谱系障碍发育迟缓（DD）。在某些方面，评估代谢物分布曲线中尾部效应的存在、不存在和/或方向（上部或下部）的信息可用于预测 ASD 的风险和/或区分 ASD 和 DD。
• Biomarkers related to organ function
  申请人：University of Pittsburgh—Of the Commonwealth System of Higher Education

  公开号：US10634686B2

  公开（公告）日：2020-04-28

  Disclosed herein are methods of identifying biomarkers (such as genes (e.g., RNA or mRNA), proteins, and/or small molecules) that can be used to predict organ or tissue function or dysfunction. In some embodiments, the methods include ex vivo perfusion of the organ or tissue, collection of samples from the organ or tissue (for example, perfusate, fluids produced by the organ (such as bile or urine), or tissue biopsies) and measuring the level of one or more biomarkers in the sample. It is also disclosed herein that an analysis of biomarkers (such as genes (e.g., RNA or mRNA), proteins, and/or small molecules) present in a biological sample from an organ, tissue, or subject can be used to identify whether the organ, tissue, or subject is at risk for (or has) organ dysfunction or organ failure.

  本文公开了鉴定可用于预测器官或组织功能或功能障碍的生物标记物（如基因（如 RNA 或 mRNA）、蛋白质和/或小分子）的方法。在一些实施方案中，这些方法包括对器官或组织进行体外灌注，收集器官或组织的样本（例如灌注液、器官产生的液体（如胆汁或尿液）或组织活检），并测量样本中一种或多种生物标记物的水平。本文还公开了对来自器官、组织或受试者的生物样本中存在的生物标记物（如基因（如 RNA 或 mRNA）、蛋白质和/或小分子）的分析，可用于确定器官、组织或受试者是否有器官功能障碍或器官衰竭的风险（或已出现器官功能障碍或器官衰竭）。
• Chemical isotope labeling-assisted liquid chromatography-mass spectrometry enables sensitive and accurate determination of dipeptides and tripeptides in complex biological samples
  作者：Feng-Qing Huang、Yu Wang、Ji-Wen Wang、Dai Yang、Shi-Lei Wang、Yuan-Ming Fan、Raphael N. Alolga、Lian-Wen Qi

  DOI：10.1016/j.cclet.2024.109670

  日期：2024.2

  their unique features and diverse biological functions. Achieving rapid separation and accurate quantification, however, remains a challenge because of their low abundance and the co-existence of numerous structural isomers. In this study, we developed a novel approach using isotope chemical labeling for ultrasensitive determination of di/tripeptides in biological samples. We successfully synthesized a

  小肽因其独特的特性和多样化的生物学功能而受到越来越多的关注。然而，由于其丰度低且存在多种结构异构体，实现快速分离和准确定量仍然是一个挑战。在这项研究中，我们开发了一种使用同位素化学标记超灵敏测定生物样品中二肽/三肽的新方法。我们成功合成了一种新型衍生化试剂4-(2-(乙氧基亚甲基)-3-氧代丁酰胺基)-三甲基苯胺碘化物(EOTMBA)及其氘标记同位素试剂(-EOTMBA)。总共97个小肽，包括89个二肽和8个三肽，在60℃下1.5小时内可以在​​甲醇中完全衍生化。 EOTMBA 标记后，通过 LC-MS/MS 分析在 22 分钟内完成对这些二肽/三肽的分析。该方法的准确度为 86.3%–113%，定量限范围为 0.25 fmol/L 至 5 nmol/L。利用该方法，我们对取自健康个体和胆道疾病患者的 147 份血浆、49 份尿液和 46 份胆汁样本中的二肽/三肽进行了超灵敏和准确的定量。
• Identification and Characterization of Prokaryotic Dipeptidyl-peptidase 5 from Porphyromonas gingivalis
  作者：Yuko Ohara-Nemoto、Shakh M.A. Rouf、Mariko Naito、Amie Yanase、Fumi Tetsuo、Toshio Ono、Takeshi Kobayakawa、Yu Shimoyama、Shigenobu Kimura、Koji Nakayama、Keitarou Saiki、Kiyoshi Konishi、Takayuki K. Nemoto

  DOI：10.1074/jbc.m113.527333

  日期：2014.2

  Background: Dipeptidyl-peptidases (DPPs) are key factors for amino acid metabolism and bacterial growth of asaccharolytic Porphyromonas gingivalis. Results: DPP5, which is specific for Ala and hydrophobic residues, is expressed in the periplasmic space of P. gingivalis.Conclusion: DPP5 was discovered in prokaryotes for the first time. Significance: The discovery of DPP5 expands understanding of amino acid and energy metabolism in prokaryotes. Porphyromonas gingivalis, a Gram-negative asaccharolytic anaerobe, is a major causative organism of chronic periodontitis. Because the bacterium utilizes amino acids as energy and carbon sources and incorporates them mainly as dipeptides, a wide variety of dipeptide production processes mediated by dipeptidyl-peptidases (DPPs) should be beneficial for the organism. In the present study, we identified the fourth P. gingivalis enzyme, DPP5. In a dpp4-7-11-disrupted P. gingivalis ATCC 33277, a DPP7-like activity still remained. PGN_0756 possessed an activity indistinguishable from that of the mutant, and was identified as a bacterial orthologue of fungal DPP5, because of its substrate specificity and 28.5% amino acid sequence identity with an Aspergillus fumigatus entity. P. gingivalis DPP5 was composed of 684 amino acids with a molecular mass of 77,453, and existed as a dimer while migrating at 66 kDa on SDS-PAGE. It preferred Ala and hydrophobic residues, had no activity toward Pro at the P1 position, and no preference for hydrophobic P2 residues, showed an optimal pH of 6.7 in the presence of NaCl, demonstrated K-m and k(cat)/K-m values for Lys-Ala-MCA of 688 m and 11.02 m(-1) s(-1), respectively, and was localized in the periplasm. DPP5 elaborately complemented DPP7 in liberation of dipeptides with hydrophobic P1 residues. Examinations of DPP- and gingipain gene-disrupted mutants indicated that DPP4, DPP5, DPP7, and DPP11 together with Arg- and Lys-gingipains cooperatively liberate most dipeptides from nutrient oligopeptides. This is the first study to report that DPP5 is expressed not only in eukaryotes, but also widely distributed in bacteria and archaea.