N-Methyl-L-aspartic acid β-tert-butyl ester
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N-Methyl-L-aspartic acid β-tert-butyl ester

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Category
L-Amino Acids
Catalog number
BAT-004070
CAS number
197632-85-2
Molecular Formula
C9H17NO4
Molecular Weight
203.30
N-Methyl-L-aspartic acid β-tert-butyl ester
IUPAC Name
(2S)-2-(methylamino)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid
Synonyms
N-Me-L-Asp(OtBu)-OH; (2S)-2-(methylamino)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid; N-METHYL-L-ASPARTIC ACID Β-TERT-BUTYL ESTER; N-Me-Asp(Otbu)-OH
Appearance
Off-white solid
Purity
≥ 98%
Density
1.136 g/cm3
Boiling Point
325.6 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C9H17NO4/c1-9(2,3)14-7(11)5-6(10-4)8(12)13/h6,10H,5H2,1-4H3,(H,12,13)/t6-/m0/s1
InChI Key
VVZMENGKDSBXFM-LURJTMIESA-N
Canonical SMILES
CC(C)(C)OC(=O)CC(C(=O)O)NC

N-Methyl-L-aspartic acid β-tert-butyl ester, a versatile chemical compound, finds diverse applications in scientific research and industry.

Neuroscience Research: Serving as a pivotal tool in brain research, N-Methyl-L-aspartic acid β-tert-butyl ester is utilized to delve into the intricacies of NMDA receptors in the brain. These receptors play crucial roles in synaptic plasticity, learning, and memory formation. By modulating the activity of NMDA receptors, researchers can probe deep into the molecular mechanisms governing cognitive processes and various neurological disorders.

Pharmacology: Within the realm of pharmacological investigations, N-Methyl-L-aspartic acid β-tert-butyl ester plays a pivotal role in the development and evaluation of novel drugs targeting NMDA receptors. It aids in unraveling the receptor’s involvement in diseases like Alzheimer’s and epilepsy. This compound is a valuable asset in high-throughput screening assays designed to identify potential therapeutic agents with precision and efficacy.

Chemical Synthesis: Positioned at the forefront of chemical synthesis, N-Methyl-L-aspartic acid β-tert-butyl ester acts as a key intermediate in the creation of intricate organic molecules. Its distinctive structure lends itself to the development of pharmaceuticals and bioactive compounds. Chemists harness its potential to explore novel synthetic routes and enhance reaction efficiencies.

Biotechnology: In the dynamic realm of biotechnology, N-Methyl-L-aspartic acid β-tert-butyl ester emerges as a crucial reagent in enzyme assays and protein interaction studies. It aids in probing the activities and specificities of enzymes involved in neurotransmitter metabolism, thereby facilitating advancements in biocatalysis research and the creation of cutting-edge biosensors for enhanced biotechnological applications.

2. Differentiation of aspartic and isoaspartic acids using electron transfer dissociation
Peter B O'Connor, Jason J Cournoyer, Sharon J Pitteri, Paul A Chrisman, Scott A McLuckey J Am Soc Mass Spectrom. 2006 Jan;17(1):15-19. doi: 10.1016/j.jasms.2005.08.019. Epub 2005 Dec 9.
Electron-transfer dissociation allows differentiation of isoaspartic acid and aspartic acid residues using the same c + 57 and z - 57 peaks that were previously observed with electron capture dissociation. These peaks clearly define both the presence and the position of isoaspartic acid residues and they are relatively abundant. The lower resolution of the ion trap instrument makes detection of the aspartic acid residue's diagnostic peak difficult because of interference with side-chain fragment ions from arginine residues, but the aspartic acid residues are still clearly observed in the backbone cleavages and can be inferred from the absence of the isoaspartic acid diagnostic ions.
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