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Application Area

N-Acetyl-DL-aspartic acid

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

β−Amino Acids

Catalog number

BAT-007715

CAS number

2545-40-6

Molecular Formula

C6H9NO5

Molecular Weight

175.14

IUPAC Name

2-acetamidobutanedioic acid

Synonyms

Ac-DL-Asp-OH; 2-Acetamidosuccinic acid; DL-Aspartic acid, N-acetyl-l; Aspartic acid, N-acetyl (R,S); 2-acetamidosuccinate; Ac-Asp; (R)-2-Acetamidosuccinic acid

Related CAS

997-55-7 (L-isomer)

Appearance

White powder

Purity

≥ 99% (TLC)

Density

1.422±0.06 g/cm3 (Predicted)

Melting Point

128-132 °C

Boiling Point

425.3±35.0 °C (Predicted)

Storage

Store at 2-8 °C

InChI

InChI=1S/C6H9NO5/c1-3(8)7-4(6(11)12)2-5(9)10/h4H,2H2,1H3,(H,7,8)(H,9,10)(H,11,12)

InChI Key

OTCCIMWXFLJLIA-UHFFFAOYSA-N

Canonical SMILES

CC(=O)NC(CC(=O)O)C(=O)O

N-Acetyl-DL-aspartic acid (N-acetylaspartate or NAA) is a chemical compound found abundantly in the brain. It is formed by combining acetic acid with aspartic acid, specifically the DL form of aspartic acid, which means it contains both the dextro (D) and levo (L) isomers. In the brain, NAA is predominantly found in neurons and is considered one of the most concentrated molecules in the central nervous system. Its precise function remains a topic of ongoing research, but it is consistently noted for its role in neuron-specific metabolic processes. NAA is thought to play a crucial role in osmoregulation, myelin synthesis, and the provision of acetate groups for lipid and acetyl-CoA synthesis, among other functions.

One of the primary applications of NAA is in the field of medical diagnostics, particularly through magnetic resonance spectroscopy (MRS). MRS is a non-invasive imaging technique that allows for the measurement of various metabolites in the brain, with NAA being a significant marker. Changes in NAA concentrations are used to assess neuronal health, as reductions in its levels are indicative of neuronal loss or dysfunction. Clinicians and researchers rely on these measurements to diagnose and monitor neurological conditions such as multiple sclerosis, Alzheimer’s disease, and brain tumors. This application underscores NAA’s critical role as a biomarker for neuronal integrity and health.

Another key application of NAA is in neuroscientific research, where its levels are studied to understand various physiological and pathological states of the brain. Researchers study fluctuations in NAA concentrations to gain insights into metabolic processes under different conditions, such as during neurodevelopment, aging, and neurological diseases. Analyzing NAA levels also contributes to understanding the impact of interventions, such as pharmacological treatments, lifestyle changes, and rehabilitation therapies on neuronal function. These studies collectively aim to enhance our understanding of brain physiology and to develop new therapeutic strategies.

Additionally, NAA has potential applications in sports science and rehabilitation, where monitoring its levels could help assess brain health in athletes. This is particularly relevant in contexts of concussion and traumatic brain injury (TBI), conditions that are prevalent in contact sports. By tracking changes in NAA levels following injury, researchers and practitioners aim to develop more effective management and recovery protocols that ensure the long-term health and performance of athletes. This application highlights the emerging role of NAA in shaping personalized and preventive sports medicine.

Finally, NAA is being explored in the field of neuropharmacology to develop new drugs and treatment approaches. Compounds that can modulate NAA levels or mimic its functional roles are being investigated for their therapeutic potential. Given NAA’s involvement in critical brain functions, pharmacological modulation of its concentration could be valuable in treating a variety of neurological disorders. This research avenue not only aims to harness the therapeutic potentials of NAA but also seeks to unravel new mechanisms of action that could lead to innovative treatments for neurodegenerative diseases.

1.Endothelin ETA and ETB receptors in subarachnoid hemorrhage-induced cerebral vasospasm.

Zuccarello M1, Lewis AI, Rapoport RM. Eur J Pharmacol. 1994 Jun 23;259(1):R1-2.

The relative roles of endothelin ETA and ETB receptor activation in cerebral vasospasm following subarachnoid hemorrhage were investigated in the rabbit. The endothelin ETA receptor antagonist, BQ610 (1 microM; homopiperidinyl-CO-Leu-D-Trp(CHO)-D-Trp-OH), and the endothelin ETA/ETB receptor antagonist, PD145065 (1 microM; Ac-D-Bhg-L-Leu-L-Asp-L-Ile-L-Ile-L-Trp), relaxed the vasospastic basilar artery in situ by 45% and 87%, respectively. These results suggest that subarachnoid hemorrhage-induced vasospasm of the rabbit basilar artery is due to activation of both endothelin ETA and ETB receptors.

2.Structure and characterization of isopyoverdin from Pseudomonas putida BTP1 and its relation to the biogenetic pathway leading to pyoverdins.

Jacques P1, Ongena M, Gwose I, Seinsche D, Schröder H, Delfosse P, Thonart P, Taraz K, Budzikiewicz H. Z Naturforsch C. 1995 Sep-Oct;50(9-10):622-9.

Pyoverdin type siderophores produced by six fluorescent Pseudomonas strains isolated from different rhizospheres were purified and characterized. The purified ferri-pyoverdins were tested for their ability to promote the growth of other strains grown under iron deficiency conditions. Only the one obtained from Pseudomonas putida BTP1 did not act as a growth promoter. The structure of the BTP1 siderophore was elucidated by spectroscopic methods and degradation studies. It turned out that it contains a chromophore which differs from the one typical for pyoverdins insofar as it carries the carboxyl group in 3- rather than in 1-position ((3S)-5-amino-1,2-dihydro-8,9-dihydroxy-3H-pyrimido[1,2a]quinoline-3- carboxylic acid). The amino group of the chromophore is substituted with the 5-carboxyl group of L-glutamic acid and its carboxyl group with the N-terminus of the peptide L-Asp-L-Ala-L-Asp-D-N5-Ac-N5-OH-Orn-L-Ser-L-c-N5-OH-Orn. This isopyoverdin fits into the biogenetic scheme which postulates ferribactins as the precursors of pyoverdins.

CYT-1010

CAT NO. : BAT-006236

MGF

CAT NO. : BAT-006153

Cyclic citrullinated peptide

CAT NO. : BAT-006243

Acetyl Tetrapeptide-11

CAT NO. : BAT-006232