(2S)-2-氨基-6-[2-甲酰基-5-(羟基甲基)吡咯-1-基]己酸 | 74509-14-1

• 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: (2S)-2-氨基-6-[2-甲酰基-5-(羟基甲基)吡咯-1-基]己酸
• 中文别名: &Epsilon-吡咯赖氨酸；Ε-吡咯赖氨酸
• 英文名称: pyrraline
• 英文别名: (2S)-2-amino-6-[2-formyl-5-(hydroxymethyl)pyrrol-1-yl]hexanoic acid
• CAS: 74509-14-1
• 化学式: C₁₂H₁₈N₂O₄
• 分子量: 254.286
• InChiKey: VTYFITADLSVOAS-NSHDSACASA-N

物化性质

• 熔点：
  >153°C (dec.)
• 沸点：
  510.1±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)
• 溶解度：
  加热、超声处理轻微溶于甲醇、轻微溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-氨基-6-[2-甲酰基-5-(羟基甲基)吡咯-1-基]己酸 在 水合茚三酮 作用下， 以 aq. acetate buffer 为溶剂， 以77%的产率得到5-(2'-formyl-5'-hydroxymethylpyrrol-1'-yl)-pentanal
  参考文献：
  名称：

  啤酒中糖化氨基酸的酵母代谢产物

  摘要：

  麦芽和酿造过程中的糖基化反应（美拉德反应）对于开发啤酒的独特颜色和风味非常重要。最近，在啤酒中发现了游离的且与蛋白质结合的美拉德反应产物（MRP），例如吡喃啉，甲酰胆碱和麦芽糖苷。此外，这些氨基酸衍生物被酿酒酵母代谢。通过埃里希路径。在这项研究中，开发了一种方法用于定量从吡喃啉，甲酸，和麦芽糖碱衍生的单个Ehrlich中间体。合成相应的参考物质后，首先对MRP衍生的新Ehrlich醇吡咯诺尔（最高207μg/ L），甲醛（最高50μg/ L）和麦芽酚（最高6.9μg/ L）进行定量。反相高效液相色谱串联质谱法在多反应监测模式下测定商业啤酒样品中的时间。这相当于ca。母体糖基化氨基酸浓度的20–40％。无酒精啤酒和麦芽饮料几乎不含代谢产物。在啤酒中对两种先前未知的缬氨酸衍生的吡咯衍生物进行了表征和定性鉴定。

  DOI：

  10.1021/acs.jafc.8b01329
• 作为产物：
  描述：

  FMOC-赖氨酸 在 哌啶 、 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 16.5h， 生成 (2S)-2-氨基-6-[2-甲酰基-5-(羟基甲基)吡咯-1-基]己酸
  参考文献：
  名称：

  单糖基高级糖基化终产物的合成及其并入胶原模型肽

  摘要：

  报道了高级糖基化终产物（AGEs），CML，CEL和吡咯啉的合成及其掺入胶原模型肽中的情况。AGEs是在蛋白质（例如胶原蛋白）上形成的修饰氨基酸，被认为在许多疾病（尤其是糖尿病）的发病机理中起着重要作用。这些化合物的合成和并入合成肽是开发用于研究AGE修饰蛋白的模型系统的关键步骤。

  DOI：

  10.1021/ol302745f

文献信息

• Transformation of Free and Dipeptide-Bound Glycated Amino Acids by Two Strains of<i>Saccharomyces cerevisiae</i>
  作者：Michael Hellwig、Marie Börner、Falco Beer、Karl-Heinz van Pée、Thomas Henle

  DOI：10.1002/cbic.201600486

  日期：2017.2.1

  Nitrogen wanted: Glycated amino acids (Maillard reaction products) are poorly utilized by S. cerevisiae. When the products are bound in dipeptides, they are translocated into the cells and transformed mainly into the corresponding α‐hydroxy acids and “Ehrlich” alcohols, which then exit the cell. Thus, S. cerevisiae is able to use glycated amino acids as a nitrogen source.

  想要的氮：酿酒酵母对糖化氨基酸（美拉德反应产物）的利用很差。当产物结合在二肽中时，它们会转移到细胞中，并主要转化为相应的α-羟酸和“艾氏”醇，然后从细胞中排出。因此，酿酒酵母能够使用糖基化的氨基酸作为氮源。
• Transport of Free and Peptide-Bound Pyrraline at Intestinal and Renal Epithelial Cells
  作者：Michael Hellwig、Stefanie Geissler、Anett Peto、Ilka Knütter、Matthias Brandsch、Thomas Henle

  DOI：10.1021/jf901224p

  日期：2009.7.22

  [14C]Gly-Sar in Caco-2 and SKPT cells with IC50 values of 0.19 and 0.017 mM, respectively. Pyrr-Ala inhibited the carrier-mediated uptake of [14C]Gly-Sar in Caco-2 and SKPT cells by 50% at concentrations of 0.03 and 0.008 mM, respectively. The transepithelial flux of peptide-bound pyrraline across Caco-2 cell monolayers was up to 15-fold higher compared to the flux of free pyrraline. We conclude that free pyrraline

  吡咯啉是食品中晚期美拉德反应的定量控制糖基化化合物，食用含吡咯啉的食品后可在尿液中发现。本研究的目的是研究吡咯啉及其二肽衍生物丙氨酰吡咯啉（Ala-Pyrr）和吡咯烷基丙氨酸（Pyrr-Ala）在肠和肾细胞系中的转运。Pyrraline抑制l- [ 3 H]赖氨酸的摄取，IC 50值分别为0.3 mM（Caco-2细胞）和3.5 mM（OK细胞），但不吸收[ 14 C] Gly-Sar（Caco-2和SKPT单元）。相比之下，Ala-Pyrr用IC 50强烈抑制Caco-2和SKPT细胞中[ 14 C] Gly-Sar的摄取值分别为0.19和0.017 mM。Pyrr-Ala分别在0.03和0.008 mM的浓度下抑制了载子介导的Caco-2和SKPT细胞中[ 14 C] Gly-Sar的摄取50％。与游离吡咯啉的通量相比，肽结合的吡咯啉跨Caco-2细胞单层的跨上皮通量高15倍。我们得出
• Antibodies to LGE.sub.2 -protein antigens
  申请人：Case Western Reserve University

  公开号：US05686250A1

  公开（公告）日：1997-11-11

  Levuglandin (LG) derivatives are used as antigens for raising antibodies useful in diagnostic assays. The antibodies produced by LG-carrier protein adducts can be used to detect adducts of LGE.sub.2 with human low density lipoprotein (LDL). LGE.sub.2 -protein adduct immunoreactivity may be generated during in vitro free-radical oxidation of LDL. An enzyme-linked immunosorbent assay for detecting adducts of LGE.sub.2 with human LDL is also described.

  Levuglandin（LG）衍生物被用作抗原，以提高在诊断测定中有用的抗体。由LG载体蛋白加合物产生的抗体可用于检测LGE.sub.2与人类低密度脂蛋白（LDL）的加合物。在体外自由基氧化LDL期间，可以产生LGE.sub.2-蛋白加合物免疫反应性。还描述了一种酶联免疫吸附测定，用于检测LGE.sub.2与人类LDL的加合物。
• Identification of New Heterocyclic Nitrogen Compounds from Glucose-Lysine and Xylose-Lysine Maillard Model Systems
  作者：Richard G. Bailey、Jennifer M. Ames、John Mann

  DOI：10.1021/jf000722+

  日期：2000.12.1

  Aqueous sugar (glucose or xylose)-lysine model systems were heated at 80 degreesC for 6 h with the pH maintained at a predetermined value (3, 4, or 5). Selected compounds were isolated by combinations of solvent extraction and semipreparative HPLC, prior to identification by NMR and mass spectrometry. Two compounds were identified from the pH 5 glucose system and were identified as epsilon-[2-formyl-5-(hydroxymethyl)pyrrole-1-yl]-L-norleucine (pyrraline) and the new compound, 1-(5-carboxy-5-aminopentyl)-2-formyl-3-(1,2,3 -trihydroxypropyl)pyrrole. A third compound was partially characterized. 2-Acetyl-5-hydroxymethyl-5,6-dihydro-4H-pyridinone was identified in the pH 3 xylose system, and the new compound, 8-furan-2-yl-methyl-5-hydroxymethyl-5,6 dione, was identified in the pH 4 xylose system. 2-Furfurylidene-4-hydroxy-5-methyl-3(2H) was identified in both xylose systems. Mechanisms of formation are proposed for the novel compounds.
• Transport of the Advanced Glycation End Products Alanylpyrraline and Pyrralylalanine by the Human Proton-Coupled Peptide Transporter hPEPT1
  作者：Stefanie Geissler、Michael Hellwig、Madlen Zwarg、Fritz Markwardt、Thomas Henle、Matthias Brandsch

  DOI：10.1021/jf903791u

  日期：2010.2.24

  The glycation compound pyrraline, which originates from the advanced Maillard reaction, appears in urine after consumption of pyrraline-containing food. We hypothesized that the absorption of pyrraline occurs in the form of dipeptides rather than the free amino acid. The human intestinal peptide transporter hPEPT1 was transiently expressed in HeLa cells. In hPEPT1-transfected cells but not in cells transfected with empty vector, the uptake of [C-14]glycylsarcosine was strongly inhibited by alanylpyrraline (Ala-Pyrr) and pyrralylalanine (Pyrr-Ala). Free pyrraline did not inhibit peptide uptake. In Xenopus laevis oocytes expressing human PEPT1, both Ala-Pyrr and Pyrr-Ala generated significant inward directed currents. In a third approach, uptake of the dipeptides into hPEPT1-transfected HeLa cells was analyzed by HPLC. Ala-Pyrr and Pyrr-Ala were taken up by hPEPT1-expressing cells at a 4- to 7-fold higher rate than by HeLa cells transfected with the empty vector. We conclude that pyrraline containing dipeptides are transported by hPEPT1 in an electrogenic manner into intestinal cells.