N-α-Methyl-L-glutamic acid hydrate
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N-α-Methyl-L-glutamic acid hydrate

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Category
L-Amino Acids
Catalog number
BAT-002092
CAS number
6753-62-4
Molecular Formula
C6H13NO5
Molecular Weight
179.17
N-α-Methyl-L-glutamic acid hydrate
IUPAC Name
(2S)-2-(methylamino)pentanedioic acid
Synonyms
N-Methyl-L-glutamic acid; (S)-2-(methylamino)pentanedioic acid; Methyl glutamic acid;N-Methylglutamic acid; H-MeGlu-OH H2O
Purity
98+%
Density
1.278 g/cm3
Boiling Point
330.2°C
Storage
Store at -20 °C
Solubility
water, 4.308e+005 mg/L @ 25 °C (est)
InChI
InChI=1S/C6H11NO4/c1-7-4(6(10)11)2-3-5(8)9/h4,7H,2-3H2,1H3,(H,8,9)(H,10,11)/t4-/m0/s1
InChI Key
XLBVNMSMFQMKEY-BYPYZUCNSA-N
Canonical SMILES
CNC(CCC(=O)O)C(=O)O
1. Interaction of Glutamic Acid/Protonated Glutamic Acid with Amide and Water Molecules: A Theoretical Study
Jia Liu, Shuang Ni, Xiumei Pan J Phys Chem A. 2022 Oct 27;126(42):7750-7762. doi: 10.1021/acs.jpca.2c05135. Epub 2022 Oct 17.
Amino acids are important nitrogen-containing compounds and organic carbon components that exist widely in the atmosphere. The formation of atmospheric aerosols is affected by their interactions with amides. The dimers formed by glutamic acid (Glu) or protonated glutamic acid (Glu+) with three kinds of amide molecules (formamide FA, acetamide AA, urea U) and the hydrated clusters formed by Glu or Glu+, U molecules along with one to six water molecules were systematically studied at the M06-2X/6-311++G(3df,3pd) level. U is predicted to form a more stable structure with Glu/Glu+ than FA and AA by thermodynamics. If the concentration ratio of FA to U is less than 104, U will play a critical role in NPF. The degree of hydration in Glu+-mU-nW is higher than that of Glu-mU-nW (m = 0, 1; n = 0-6) clusters. Notably, Glu contributes more to the Rayleigh scattering properties than glutaric acid and sulfuric acid, and thus may lead to the destruction of atmospheric visibility. This study is helpful to better understand the properties of organic aerosols containing amino acids or amides.
2. Towards the biodegradation pathway of fosfomycin
K Pallitsch, A Schweifer, A Roller, F Hammerschmidt Org Biomol Chem. 2017 Apr 11;15(15):3276-3285. doi: 10.1039/c7ob00546f.
Three functionalised propylphosphonic acids were synthesised to study C-P bond cleavage in R. huakuii PMY1. (R)-1-Hydroxy-2-oxopropylphosphonic acid [(R)-5] was prepared by chiral resolution of (±)-dimethyl 1-hydroxy-2-methylallyllphosphonate [(±)-12], followed by ozonolysis and deprotection. The N-(l-alanyl)-substituted (1R,2R)-2-amino-1-hydroxypropylphosphonic acid 10, a potential precursor for 2-oxopropylphosphonic acid (5) in cells, was obtained by coupling the aminophosphonic acid with benzotriazole-activated Z-l-alanine and hydrogenolytic deprotection. (1R*,2R*)-1,2-Dihydroxy-3,3,3-trifluoropropylphosphonic acid, a potential inhibitor of C-P bond cleavage after conversion into its 2-oxo derivative in the cell, was accessed from trifluoroacetaldehyde hydrate via hydroxypropanenitrile 21, which was silylated and reduced to the aldehyde (±)-23. Diastereoselective addition of diethyl trimethylsilyl phosphite furnished diastereomeric α-siloxyphosphonates. The less polar one was converted to the desired racemic phosphonic acid (±)-(1R*,2R*)-9 as its ammonium salt.
3. α-TCP-based calcium phosphate cements: A critical review
Matheus C Tronco, Júlia B Cassel, Luís A Dos Santos Acta Biomater. 2022 Oct 1;151:70-87. doi: 10.1016/j.actbio.2022.08.040. Epub 2022 Aug 24.
Calcium phosphates are promising materials for applications in bone repair and substitution, particularly for their bioactivity and ability to form self-setting cements. Among them, α-tricalcium phosphate (α-TCP) stands out due to its high solubility, its hydration reaction and bioresorbability. The synthesis of α-TCP is particularly complex and the interactions between some of the synthesis parameters are still not completely understood. The variety of methods available to synthesize α-TCP has provided a substantial variance in the properties of α-TCP-based cements and the decision about which method, parameters and starting reagents will be used for the powder's synthesis is determinant of the properties of the resulting material. Therefore, this review paper focuses on α-TCP's synthesis and properties, presenting the synthesis methods currently in use as well as a discussion of how the synthesis parameters and the cement preparation affect the reactivity and mechanical properties of the material, providing a guide for the selection of the most suitable process for each α-TCP application. STATEMENT OF SIGNIFICANCE: α-TCP is a calcium phosphate and it is currently one of the most investigated bioceramics for applications that explore its bioresorbability and the hydration reaction of α-TCP-based cements. Despite the increasing number of publications on the topic, there are still aspects not well understood. This review article aims at contributing to this fascinating subject by offering an update on the state of the art of α-TCP's synthesis methods, while also addressing topics that are not often discussed about this material, such as the preparation of α-TCP-based cements and how its parameters affect the properties of the resulting cements.
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