tert-butoxycarbonyl-L-lysyl-L-alanine | 78461-23-1

• 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
• 英文名称: tert-butoxycarbonyl-L-lysyl-L-alanine
• 英文别名: Boc-Lys-Ala-OH；Boc-Lys-Ala
• CAS: 78461-23-1；31310-98-2
• 化学式: C₁₄H₂₇N₃O₅
• 分子量: 317.385
• InChiKey: MNLBMUMNKYZUDI-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  130.75
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butoxycarbonyl-L-lysyl-L-alanine 在 palladium on activated charcoal 、 氢气 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 20.0~70.0 ℃ 、101.33 kPa 条件下， 反应 52.0h， 生成
  参考文献：
  名称：

  游离和肽结合的糖基化氨基酸的运输：合成，Caco-2细胞单层上皮上皮通量以及与顶端膜转运蛋白的相互作用。

  摘要：

  美拉德变相：作为小氨基酸施用时，美拉德反应产物（MRP）不会渗透Caco-2单层。然而，结合在二肽中，MRP以依赖于它们的结构的方式转运到细胞中。许多美拉德二肽是肽转运蛋白PEPT1的底物。细胞内水解后，MRP穿过细胞的基底外侧膜离开细胞。

  DOI：

  10.1002/cbic.201000759
• 作为产物：
  描述：

  N^α-tert-butyloxycarbonyl-N^ε-benzyloxycarbonyllysyl-alanine 在 钯 氢气 作用下， 生成 tert-butoxycarbonyl-L-lysyl-L-alanine
  参考文献：
  名称：

  Skalaban,T.D. et al., Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 47 - 50

  摘要：

  DOI：

文献信息

• 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
• 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.
• Design of high-affinity peptide conjugates with optimized fluorescence quantum yield as markers for small peptide transporter PEPT1 (SLC15A1)
  作者：Praveen M. Bahadduri、Abhijit Ray、Akash Khandelwal、Peter W. Swaan

  DOI：10.1016/j.bmcl.2008.03.044

  日期：2008.4

  We employed a computational approach to design and synthesize a series of. fluorescently labeled hPEPT1 substrates. Five Alexa Fluor-350 (TM)-labeled peptides were assessed for their in vitro inhibitory activity in hPEPT1-transfected CHO cells. At least four labeled peptides show potent inhibitory activity toward hPEPT1-mediated uptake of [H-3]-GlySar and three compounds displayed a significant cellular uptake specifically mediated by hPEPT1. (c) 2008 Elsevier Ltd. All rights reserved.