N-(1-deoxy-fructos-1-yl)glutamic acid | 60644-23-7

• 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: N-(1-deoxy-fructos-1-yl)glutamic acid
• 英文别名: (2S)-2-[[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methylamino]pentanedioic acid
• CAS: 60644-23-7
• 化学式: C₁₁H₁₉NO₉
• 分子量: 309.273
• InChiKey: RHYOFQJYHNHREU-VISRLPHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  disodium N-(2,3:4,5-di-O-isopropylidene-1-deoxy-β-D-fructos-1-yl)-L-glutamate 在 三氟乙酸 作用下， 反应 2.0h， 以82%的产率得到N-(1-deoxy-fructos-1-yl)glutamic acid
  参考文献：
  名称：

  Synthesis and Sensory Characterization of Novel Umami-Tasting Glutamate Glycoconjugates

  摘要：

  Two glycoconjugates of glutamic acid, namely, the N-glycoside dipotassiurn N-(D-glucos-1-yl)-L-glutamate (1) and the corresponding Amadori compound N-(1-deoxy-D-fructos-1-yl)-L-glutamic acid (2), have been synthesized in yields of 35 and 52%, respectively, using new Maillard-mimetic approaches, and their chemical structures have unequivocally been elucidated by 1D- and 2D-NMR and MS experiments. Systematic sensory studies revealed that both glycoconjugates exhibit pronounced umami-like taste with recognition taste thresholds of 1-2 mmol/L, close to that of monosodium glutamate (MSG). Contrary to an aqueous solution of MSG, 1 does not show the sweetish and slightly soapy by-note, but evokes an intense umami taste. Aqueous solutions of 2 were described by the descriptors umami, seasoning, and bouillon-like. Added to a bouillon base, which did not contain any taste enhancers, both glycoconjugates imparted a distinct umami character similar to the control sample containing the same amount of MSG on a molar basis. To the best of our knowledge, these types of glycoconjugates in general and, in particular, N-glucosyl glutamate and N-deoxyfructosyl glutamate have never been reported as taste active compounds having umami-like properties. Therefore, 1 and 2 represent a new class of umami-type taste compounds showing properties similar to the umami reference compound MSG. Systematic (13)C NMR measurements revealed that 1 was fairly stable in aqueous solutions under alkaline conditions (pH 8-10) as well as in dry form. However, it rapidly hydrolyzes in neutral and acidic solutions, giving rise to glucose and glutamate. In contrast, glycoconjugate 2 was observed to be rather stable in aqueous solution as well as in the presence of human saliva.

  DOI：

  10.1021/jf0344441

文献信息

• [EN] ORAL CARE COMPOSITION COMPRISING AN AMADORI COMPOUND<br/>[FR] COMPOSITION D'HYGIÈNE BUCCALE COMPRENANT UN COMPOSÉ AMADORI
  申请人：COLGATE PALMOLIVE CO

  公开号：WO2014098793A1

  公开（公告）日：2014-06-26

  The present invention relates to oral care compositions and methods of inhibiting microbial biofilm formation and/or degrading a microbial biofilm. Disclosed herein are oral care compositions comprising an Amadori compound having a glucose moiety and an amino acid moiety. The Amadori compound has use for inhibiting oral microbial biofilm formation and/or degrading an oral microbial biofilm in the oral cavity of a mammalian subject.

  本发明涉及口腔护理组合物和抑制微生物生物膜形成和/或降解微生物生物膜的方法。本文公开了口腔护理组合物，其中包括具有葡萄糖基团和氨基酸基团的阿马多利化合物。该阿马多利化合物可用于抑制哺乳动物主体口腔中的口腔微生物生物膜形成和/或降解口腔微生物生物膜。
• Maillard Mimetic Food-Grade Synthesis of <i>N</i>-(β-<scp>d</scp>-Deoxyfructos-1-yl)-<scp>l</scp>-glutamic Acid and <i>N</i>-(β-<scp>d</scp>-Deoxyfructos-1-yl)-β-alanyl-<scp>l</scp>-histidine by a Combination of Lyophilization and Thermal Treatment
  作者：Jianan Zhang、Mouming Zhao、Nanxi Gao、Guowan Su、Baoguo Sun、Jiahui Zhang、Chi-Tang Ho

  DOI：10.1021/acs.jafc.0c03009

  日期：2020.7.29

  acid, namely, N-(β-d-deoxyfructos-1-yl)-l-glutamic acid, was successfully synthesized as the primary isomer in a yield of 96.08% using a food-grade preparation method, and its chemical structure was clearly demonstrated by mass spectrometry and 1D/2D NMR. The reaction kinetics of glucose and glutamic acid were systematically studied to investigate the effect of lyophilization and thermal treatment on

  谷氨酸的典型糖缀合物，即ñ - （β- d -deoxyfructos -1-基） -升用食品级制备方法成功合成了β-谷氨酸作为主要异构体，收率为96.08％，其化学结构已通过质谱和1D / 2D NMR明确证实。系统地研究了葡萄糖和谷氨酸的反应动力学，以研究冻干和热处理对反应物转化为相应的Amadori重排产物（ARP）的影响。有趣的是，除了初始的pH值，温度和加热时间外，谷氨酸的初始浓度还影响了最终的收率，因为分子内的脱水同时发生，与美拉德反应和降解反应竞争。此外，还以约66的产率制备了类似的肌肽的Amadori化合物。条件优化后，收率可达38％，收率可进一步提高到95％。确认该肽的相应ARP的一种主要异构体是通过结构表征获得N-（β- d-脱氧果糖-1-基）-β-丙氨酰基-1-组氨酸，表明这是制备N-（β- d-脱氧果糖-1-基）-氨基的良好方法酸/肽。
• Impact of drying techniques, seasonal variation and organic growing on flavor compounds profiles in two Italian tomato varieties
  作者：Dario Paolo、Giulia Bianchi、Carlo Francesco Morelli、Giovanna Speranza、Gabriele Campanelli、Ulla Kidmose、Roberto Lo Scalzo

  DOI：10.1016/j.foodchem.2019.125062

  日期：2019.11

  The industrial transformation of tomato (Lycopersicon esculentum Mill.) produces processed foods, such as dried tomatoes. In this study two varieties (SaAb and PerBruzzo), grown in three cropping systems (one conventional and two organic ones), were processed by two types of small-scale drying (oven or sun drying), over two years of production. The dried samples were analyzed for their non-volatile and volatile composition, relating the results with sensory analysis. The multivariate analysis performed on collected data allowed a detailed comparison of the effects of processing, year-to year variation and cropping systems. Results indicated that drying methods mainly influenced the composition and flavor profile, also affected by the production year. The cropping system significantly influenced some quality indices, such as the acid and sugar amounts, and the aldehydes, respectively higher and lower in organic samples. The comprehensive PCA analysis allowed discrimination of drying methods and, to a lesser extent, cropping systems.
• Metabolic Profiling Approach To Explore Compounds Related to the Umami Intensity of Soy Sauce
  作者：Kazuki Shiga、Shinya Yamamoto、Ayako Nakajima、Yukako Kodama、Miho Imamura、Tsuneo Sato、Riichiro Uchida、Akio Obata、Takeshi Bamba、Eiichiro Fukusaki

  DOI：10.1021/jf501173r

  日期：2014.7.23

  A metabolic profiling approach was employed to explore the compounds that affect the intensity of umami taste in soy sauce. Twenty-five kinds of soy sauces were analyzed using GC-MS and LC-MS, wherein measurement data for 427 compounds were obtained. The umami taste intensity of each soy sauce sample was also quantitated by sensory evaluation and a projection to latent structure (PLS) regression analysis was conducted using the compounds' measurements and umami taste intensity data. Variable importance for the projection (VIP) value obtained via PLS was used for the estimation of the relevance for umami taste intensity. N-(1-Deoxyfructos-1-yl)glutamic acid (Fru-Glu) had the highest VIP value, and addition of Fru-Glu to soy sauce increased umami taste intensity better than glutamic acid at the same concentration as confirmed by sensory evaluation. This study showed that the combination of metabolic profiling approach and sensory evaluation can be used effectively to determine compounds related to taste.
• Electrospray positive ionization tandem mass spectrometry of Amadori compounds
  作者：Jun Wang、Yi-Min Lu、Bai-Zhan Liu、He-Yong He

  DOI：10.1002/jms.1290

  日期：2008.2