1-(N-色氨酸)-1-脱氧果糖 | 25020-15-9

• 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: 1-(N-色氨酸)-1-脱氧果糖
• 中文别名: 3-(2-叠氮-10,11-二氢-5H-二苯并[b,f]吖庚英-5-基)-N,N-二甲基丙烷-1-胺
• 英文名称: N-(1-deoxy-D-fructos-1-yl)-L-tryptophan
• 英文别名: D-Fructose, 1-((1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-1-deoxy-, (S)-；(2S)-3-(1H-indol-3-yl)-2-[[(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexyl]amino]propanoic acid
• CAS: 25020-15-9
• 化学式: C₁₇H₂₂N₂O₇
• 分子量: 366.371
• InChiKey: RZJHOCXJFBBOAY-LCGIIJARSA-N

物化性质

• 熔点：
  >125°C (dec.)
• 沸点：
  786.0±60.0 °C(Predicted)
• 密度：
  1.511±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（少许）、甲醇（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  163
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(N-色氨酸)-1-脱氧果糖 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 6.0h， 以31%的产率得到N-(1-Desoxy-D-fructos-1-yl)-N-nitroso-L-tryptophan
  参考文献：
  名称：

  N-（1-脱氧-d-果糖-1-YL）-N-亚硝基-1-氨基脲的NMR分析和分析（“ N-亚硝基0-果糖氨基脲”）

  摘要：

  摘要通过亚硝酸钠亚硝化相应的“果糖氨基酸”，制备了13种N-（1-脱氧-d-果糖-1-基）-N-亚硝基-1-氨基酸，产率为83-95％。在pH值为3的盐酸水溶液中。1 Hn.mr光谱由于存在不同的糖环形式（α，β-呋喃糖和吡喃糖）而变得复杂。另外，对于E / Z异构体N-亚硝基化合物，观察到所有质子共振的信号加倍。在溶液平衡中，β-d-吡喃糖的信号可以明确地确定为> 50％。在D 2 O中，某些化合物对H-1a和H-1b的HD交换缓慢。所有E / Z异构体β-吡喃糖的环构象为2 C 5（d）。13 Cn.mr光谱显示出所有四个环的共振，E / Z异构体的信号加倍，所有这些均可分配。不存在开链形式的信号。对于β-d-吡喃糖形式，通过与离析物（Δδ值）进行比较，计算了由N-亚硝化引起的化学位移的变化，并分别讨论了E-和Z-异构体。报道了亚硝基衍生物的反相分离，离子对，LC和pKa值，以及它们的

  DOI：

  10.1016/0008-6215(87)80131-3
• 作为产物：
  描述：

  葡萄糖 、 L-色氨酸 在 sodium disulfite 作用下， 以 甲醇 、 水 为溶剂， 反应 2.5h， 以5.4%的产率得到1-(N-色氨酸)-1-脱氧果糖
  参考文献：
  名称：

  N-（1-脱氧-d-果糖-1-基）-1-氨基酸（“果糖氨基酸”）的Nmr光谱

  摘要：

  摘要多重旋转的N-（1-deoxy-d -fructos-1-yl）-1-氨基酸（1 H-（360和400 MHz）和13 Cn.mr（90.52和100.57 MHz）的高分辨率光谱（据报道，D 2 O中的“果糖氨基酸” 1-14。1 H光谱可明确分配主要成分（β-吡喃糖形式）的信号。其他形式的信号不能很好地解析，因此无法解释。1–14的13 C光谱显示〜64％的β-吡喃糖，〜15％的α-呋喃糖，〜15％的β-呋喃糖和6％的α-吡喃糖形式。对于N-（1-脱氧-d-果糖-1-基）-1-丙氨酸（2），存在2％的酮形式。在D 2 O中的溶液中，果糖部分的H-1经历缓慢的H / D交换，这在更碱性的pH值下会大大加速。如13 Cn.mr光谱所揭示的，化合物2在0.7-11.9的pH范围内是稳定的。给出了由质子化/去质子化引起的13 C位移变化。随着pH的变化，各种形式的比率没有显着变化。

  DOI：

  10.1016/0008-6215(83)88108-7

文献信息

• The pyridoxamine action on Amadori compounds: A reexamination of its scavenging capacity and chelating effect
  作者：Miquel Adrover、Bartolomé Vilanova、Juan Frau、Francisco Muñoz、Josefa Donoso

  DOI：10.1016/j.bmc.2008.04.002

  日期：2008.5

  Amadori compounds act as precursors in the formation of advanced glycation end products (AGEs) by non-enzymatic protein glycation, which are involved in ensuing protein damage. Pyridoxamine is a potent drug against protein glycation, and can act on several pathways in the glycation process. Nevertheless, the pyridoxamine inhibition action on Amadori compounds oxidation is still unclear. In this work, we have studied the Schiff base formation between pyridoxamine and various Amadori models at pH 7.4 at 37 degrees C in the presence of NaCNBH(3). We detected an adduct formation, which suggests that pyridoxamine reacts with the carbonyl group in Amadori compounds. The significance of this mechanism is tested by comparison of the obtained kinetics rate constants with that obtained for 4-(aminomethyl)-pyridine, a structural analogue of pyridoxamine without post-Amadori action. We also study the chelating effect of pyridoxamine on metal ions. We have determined the complexation equilibrium constants between pyridoxamine, N-(1-deoxy-D-fructos-1-yl)-L-tryptophan, aminoguanidine, and ascorbic acid in the presence of Zn(2+). The results show that the strong stability of pyridoxamine complexes is the key in its post-Amadori inhibition action. On the other hand results explain the lack of inhibition of aminoguanidine ( a glycation inhibitor) in the post-Amadori reactions. (C) 2008 Elsevier Ltd. All rights reserved.
• The role of methylglyoxal in the non-enzymatic conversion of tryptophan, its methyl ester and tryptamine to 1-acetyl-β-carbolines
  作者：Ina Nemet、Lidija Varga-Defterdarović

  DOI：10.1016/j.bmc.2008.02.039

  日期：2008.4

  Non-enzymatic modi. cation of L-tryptophan ( 1) and its metabolites and derivatives with aldehydes, via the Pictet-Spengler reaction, affords beta-carbolines. Here we demonstrate that methylglyoxal ( 2) generates 1-acetyl-beta-carbolines from tryptophan ( 1), from its methyl ester ( 6) and from tryptamine ( 4); however, 2 did not generate 1-(1-hydroxyethyl)-beta-carboline derivates. HPLC analysis of model reaction systems showed formation of 1-acetyl-beta-carboline ( 3) and 1-acetyl-beta-carboline-3-carboxylic acid ( 5) during incubation of 1 and 2, at pH 5.7 and 7.4, at 100 degrees C, and only 5 at 37 degrees C, at the same pH values, with limited access of oxygen. Aerobic conditions caused higher formation of 3 at 37 degrees C at both pH values, while, at higher temperature, the same effect was only observed at pH5.7. Lack of oxygen did not much influence the formation of 3 or 5 at both pH and temperature values, in comparison with the formation at limited access of oxygen. Incubation of 2 and 6 generated methyl-1-acetyl-beta-carboline-3-carboxylate ( 7) together with 3 and 5 as a result of hydrolysis of 6 into 1 and, partially, 7 into 5, while in incubation mixtures of 2 and 4 only unstable 1-acetyl-3,4-dihydro-beta-carboline ( 8) was observed. Incubation of 1 with D-glucose as well as incubation of tryptophan with Amadori product 18 under similar conditions did not generate carbolines 3 or 5. For the first time, we were able to demonstrate the presence of 1-acetyl-beta-carboline-3-carboxylic acid ( 5) in some commercially available ketchups and in previously heated tomato concentrate. (c) 2008 Elsevier Ltd. All rights reserved.
• Formation of Tetrahydro-β-carbolines and β-Carbolines during the Reaction of <scp>l</scp>-Tryptophan with <scp>d</scp>-Glucose
  作者：Birgit Rönner、Holger Lerche、Wolfgang Bergmüller、Christine Freilinger、Theodor Severin、Monika Pischetsrieder

  DOI：10.1021/jf991237l

  日期：2000.6.1

  The reaction of L-tryptophan (Trp) with D-glucose under conditions that can occur during food processing and preparation was studied by high-performance liquid chromatography with diode array detection (HPLC/DAD). Besides the well-established glucose-tryptophan Amadori product (AP), (1R,3S)-1-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (PHP-TH beta C) was identified as an important product of this reaction. For preparation, PHP-TH beta C was obtained in high yields when Trp and D-glucose were reacted under strongly acidic conditions after heating in methanol. At elevated reaction temperatures (150 degrees C) 1-acetyl-beta-carboline (acetyl-beta C), was detected in significant concentrations. The mixtures were heated under variations of reaction time and temperature, and AP, PHP-TH beta C, and acetyl-beta C were quantified. In the presence of air oxygen or mild, food relevant oxidants, such as L-dehydroascorbic acid, PHP-TH beta C was readily oxidized to a product that was identified as the previously unknown 1-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-beta-carboline (PHP-beta C). Formation of PHP-TH beta C and PHP-beta C in foodstuffs would deserve particular interest because multiple physiological activity of TH beta C and beta C derivatives has been shown previously.