Need Assistance?

US & Canada:
+
UK: +

FAQs

Resources

Our Highlights

GMP Grade Efficient workshop for GMP production.
Optimal Prices Buying products on this site guarantees the best price!
Commercial Batches Independent GMP manufacturing suites that handle commercial batches
Prompt Delivery Warehouses in multiple cities to ensure timely delivery
Flexible Quantity Quantities available from milligrams to ton

Application Area

α-Me-Asp-OH

* 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-008915

CAS number

3227-17-6

Molecular Formula

C5H9NO4

Molecular Weight

147.13

IUPAC Name

(2S)-2-amino-2-methylbutanedioic acid

Synonyms

H-aMeAsp-OH; 2-Methyl-L-Aspartic Acid; alpha-methylaspartic acid; alpha-Me-Asp-OH; α Me Asp OH; alpha Me Asp OH

Purity

95%

Density

1.414g/cm3

Boiling Point

259.2°C at 760 mmHg

InChI

InChI=1S/C5H9NO4/c1-5(6,4(9)10)2-3(7)8/h2,6H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1

InChI Key

CWAYDJFPMMUKOI-YFKPBYRVSA-N

Canonical SMILES

CC(CC(=O)O)(C(=O)O)N

α-Me-Asp-OH, short for α-Methylaspartic Acid, is a derivative of aspartic acid where a methyl group is attached to the alpha carbon. This compound falls within the class of non-proteinogenic amino acids, which means it is not among the amino acids traditionally incorporated into proteins. Despite this, compounds such as α-Me-Asp-OH can play crucial roles in biological systems and serve as important tools in biochemical research. Its unique structure, featuring a methyl group on the alpha carbon, can lead to distinct chemical properties and biological activities compared to standard aspartic acid. This can be particularly useful in modifying biochemical pathways or the properties of peptides.

One key application area of α-Me-Asp-OH is in the study of enzyme-substrate specificity. By replacing standard aspartic acid with α-Me-Asp-OH in substrates or enzyme analogs, researchers can investigate how modifications affect enzyme activity and specificity. This type of substitution can provide insights into the active site of enzymes and help map out how enzymes interact with substrates. Such studies are invaluable in drug discovery and in designing inhibitors targeting specific enzymes, as understanding these details can lead to the development of more effective pharmaceuticals.

Another significant application is in the field of drug design, particularly in creating more stable peptide drugs. The introduction of α-Me-Asp-OH into peptide chains can enhance their resistance to proteolytic degradation, which is a common challenge in developing peptide-based therapeutics. By conferring increased stability, α-Me-Asp-OH can extend the half-life of therapeutic peptides, improving their efficacy and reducing the frequency with which they must be administered. This property makes it a valuable tool in synthesizing more robust drug candidates.

In the development of biomaterials, α-Me-Asp-OH might be employed to influence the physical properties of synthetic polymers and hydrogels. Amino acids like α-Me-Asp-OH can be used to introduce specific chemical functionalities into biomaterials, thereby modulating their interaction with biological tissues. This can be crucial in developing materials for tissue engineering and regenerative medicine applications, where tailor-made interactions between materials and cells are required to achieve desired therapeutic outcomes.

The educational utility of α-Me-Asp-OH also represents a significant area of application. It can serve as a teaching tool in advanced chemistry and biochemistry courses, illustrating concepts such as stereochemistry, amino acid modification, and substrate mimicry. Providing practical lab experience with α-Me-Asp-OH enables students to explore the complexities of amino acid chemistry and its implications in research and therapy development, thus fostering a deeper understanding of these fundamental biochemical principles.

1.Ultra-trace graphene oxide in a water environment triggers Parkinson's disease-like symptoms and metabolic disturbance in zebrafish larvae.

Ren C1, Hu X2, Li X3, Zhou Q4. Biomaterials. 2016 Mar 31;93:83-94. doi: 10.1016/j.biomaterials.2016.03.036. [Epub ahead of print]

Over the past decade, the safety of nanomaterials has attracted attention due to their rapid development. The relevant health threat of these materials remains largely unknown, particularly at environmentally or biologically relevant ultra-trace concentrations. To address this, we first found that graphene oxide (GO, a carbon nanomaterial that receives extensive attention across various disciplines) at concentrations of 0.01 μg/L-1 μg/L induced Parkinson's disease-like symptoms in zebrafish larvae. In this model, zebrafish showed a loss of more than 90% of dopamine neurons, a 69-522% increase in Lewy bodies (α-synuclein and ubiquitin) and significantly disturbed locomotive activity. Moreover, it was also shown that GO was able to translocate from the water environment to the brain and localize to the nucleus of the diencephalon, thereby inducing structural and morphological damage in the mitochondria. Cell apoptosis and senescence were triggered via oxidative stress, as shown by the upregulation of caspase 8 and β-galactosidase.

2.Antioxidant capacity of different cheeses: Affecting factors and prediction by near infrared spectroscopy.

Revilla I1, González-Martín MI2, Vivar-Quintana AM3, Blanco-López MA3, Lobos-Ortega IA4, Hernández-Hierro JM5. J Dairy Sci. 2016 Apr 13. pii: S0022-0302(16)30171-0. doi: 10.3168/jds.2015-10564. [Epub ahead of print]

In this study, we analyzed antioxidant capacity of 224 cheese samples prepared using 16 varied mixtures of milk from cows, ewes, and goats, in 2 manufacturing seasons (winter and summer), and over 6 mo of ripening. Antioxidant capacity was evaluated using the spectrophotometric 2,2-azinobis(3-ethylenebenzothiazoline-6-sulfonic acid) (ABTS) method. Total antioxidant capacity was significantly correlated with season of manufacturing and time of ripening but not with animal species providing the milk. Moreover, statistically significant correlations between the total antioxidant capacity and retinol (r = 0.399), fat percentage (r = 0.308), protein percentage (r = 0.366), K (r = 0.385), Mg (r = 0.312), Na (r = 0.432), and P (0.272) were observed. We evaluated the use of near infrared spectroscopy technology, together with the use of a remote reflectance fiber-optic probe, to predict the antioxidant capacity of cheese samples. The model generated allowed us to predict antioxidant capacity in unknown cheeses of different compositions and ripening times.

3.Design and synthesis of some novel 4-Chloro-N-(4-(1-(2-(2-cyanoacetyl)hydrazono)ethyl)phenyl) benzenesulfonamide derivatives as anticancer and radiosensitizing agents.

Ghorab MM1, Ragab FA2, Heiba HI3, Soliman AM3. Eur J Med Chem. 2016 Apr 6;117:8-18. doi: 10.1016/j.ejmech.2016.04.009. [Epub ahead of print]

A novel series of sulfonamide derivatives 4-21 have been synthesized starting from the strategic starting material (E)-4-Chloro-N-(4-(1-(2-(2-cyanoacetyl)hydrazono)ethyl)phenyl) benzenesulfonamide 4. Two series of hydrazone 5-9, and pyridone 10-21 derivatives bearing a sulfonamide moiety were obtained. All the newly synthesized compounds were evaluated for their in vitro cytotoxic activity against human liver cancer cell line (HepG2). Compounds 4-6, 8, 9, 10-14 and 16-18 showed higher activity compared to doxorubicin as a positive control. The radiosensitizing ability of the most promising compounds 4, 10 and 12 was studied which showed an increase in the cell killing effect of γ-radiation after combination with these derivatives. The molecular design was performed to predict the binding mode of the most promising compounds 4, 10 and 12 with the active site of hCA IX, that showed appropriate fitting with the relevant amino acids in the binding pocket on the basis of standard bond lengths, angles, S score and E conformation data.

4.The mutation spectrum in genomic late replication domains shapes mammalian GC content.

Kenigsberg E1, Yehuda Y2, Marjavaara L3, Keszthelyi A3, Chabes A4, Tanay A5, Simon I6. Nucleic Acids Res. 2016 Apr 16. pii: gkw268. [Epub ahead of print]

Genome sequence compositions and epigenetic organizations are correlated extensively across multiple length scales. Replication dynamics, in particular, is highly correlated with GC content. We combine genome-wide time of replication (ToR) data, topological domains maps and detailed functional epigenetic annotations to study the correlations between replication timing and GC content at multiple scales. We find that the decrease in genomic GC content at large scale late replicating regions can be explained by mutation bias favoring A/T nucleotide, without selection or biased gene conversion. Quantification of the free dNTP pool during the cell cycle is consistent with a mechanism involving replication-coupled mutation spectrum that favors AT nucleotides at late S-phase. We suggest that mammalian GC content composition is shaped by independent forces, globally modulating mutation bias and locally selecting on functional element. Deconvoluting these forces and analyzing them on their native scales is important for proper characterization of complex genomic correlations.