potassium salt of (S)-glutamic acid

• 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: potassium salt of (S)-glutamic acid
• 英文别名: dipotassium L-glutamate；potassium L-glutamate；potassium glutamate；potassium hydrogenglutamate；potassium mono-L-glutamate；potassium;(2S)-2-aminopentanedioate
• 化学式: C₅H₇NO₄*2K
• 分子量: 223.311
• InChiKey: HQEROMHPIOLGCB-DFWYDOINSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -6.4
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  106.28
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-amino-3,4-dihydro-3-methyl-2-methoxy-5-nitroso-4-oxopyrimidine 、 potassium salt of (S)-glutamic acid 以 甲醇 为溶剂， 反应 48.0h， 生成 N-(4-amino-1-methyl-5-nitroso-6-oxo-1,6-dihydropyrimidin-2-yl)-(S)-glutamic acid
  参考文献：
  名称：

  N-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)-(S)-glutamic acid: a three-dimensional framework structure built from O—H...O, N—H...O and O—H...N hydrogen bonds

  摘要：

  The title compound, C10H13N5O6, exhibits a highly polarized molecular-electronic structure and the conformation is influenced by two intramolecular N-H...O hydrogen bonds. The molecules are linked into a single framework by hydrogen bonds of types O-H...O [O-H = 1.22, H...O = 1.38, O...O = 2.558 (6) Angstrom and O-H...O = 160 degrees], N-H...O [H...O = 2.26, N...O = 2.866 (6) Angstrom and N-H...O = 126 degrees] and O-H...N [O-H = 1.26, H...N = 1.56, O...N = 2.811 (6) Angstrom and O-H...N = 170degrees]. The substructure generated by the O-H...O and N-H...O hydrogen bonds takes the form of a double helix.

  DOI：

  10.1107/s0108270103005754

文献信息

• Synthesis and Sensory Characterization of Novel Umami-Tasting Glutamate Glycoconjugates
  作者：Ersan Beksan、Peter Schieberle、Fabien Robert、Imre Blank、Laurent Bernard Fay、Hedwig Schlichtherle-Cerny、Thomas Hofmann

  DOI：10.1021/jf0344441

  日期：2003.8.1

  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.
• Abdullah, Mohammed; Barrett, Jack; O'Brien, Paul, Journal of the Chemical Society, Dalton Transactions
  作者：Abdullah, Mohammed、Barrett, Jack、O'Brien, Paul

  DOI：——

  日期：——
• <i>N</i>-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)-(<i>S</i>)-glutamic acid: a three-dimensional framework structure built from O—H...O, N—H...O and O—H...N hydrogen bonds
  作者：Paloma Arranz Mascarós、M. Dolores Gutiérrez Valero、John N. Low、Christopher Glidewell

  DOI：10.1107/s0108270103005754

  日期：2003.4.15

  The title compound, C10H13N5O6, exhibits a highly polarized molecular-electronic structure and the conformation is influenced by two intramolecular N-H...O hydrogen bonds. The molecules are linked into a single framework by hydrogen bonds of types O-H...O [O-H = 1.22, H...O = 1.38, O...O = 2.558 (6) Angstrom and O-H...O = 160 degrees], N-H...O [H...O = 2.26, N...O = 2.866 (6) Angstrom and N-H...O = 126 degrees] and O-H...N [O-H = 1.26, H...N = 1.56, O...N = 2.811 (6) Angstrom and O-H...N = 170degrees]. The substructure generated by the O-H...O and N-H...O hydrogen bonds takes the form of a double helix.