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

Z-N-methyl-D-alanine

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

Category

CBZ-Amino Acids

Catalog number

BAT-003393

CAS number

68223-03-0

Molecular Formula

C12H15NO4

Molecular Weight

237.2

IUPAC Name

(2R)-2-[methyl(phenylmethoxycarbonyl)amino]propanoic acid

Synonyms

Z-N-Me-D-Ala-OH; N-METHYL-N-CBZ-D-ALANINE

Appearance

Solid

Purity

99%

Density

1.222±0.06 g/cm3(Predicted)

Melting Point

215-219 °C

Boiling Point

389.5±31.0 °C(Predicted)

Storage

Store at 2-8°C

InChI

InChI=1S/C12H15NO4/c1-9(11(14)15)13(2)12(16)17-8-10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3,(H,14,15)/t9-/m1/s1

InChI Key

QGEQKVZQPWSOTI-SECBINFHSA-N

Canonical SMILES

CC(C(=O)O)N(C)C(=O)OCC1=CC=CC=C1

Z-N-methyl-D-alanine (MeD-Ala), a non-proteinogenic amino acid, is a versatile compound with applications spanning biochemical and pharmaceutical research. Here are the key applications of Z-N-methyl-D-alanine presented with high perplexity and burstiness:

Peptide Synthesis: Playing a pivotal role in drug development, Z-N-methyl-D-alanine is integrated into peptide synthesis processes to enhance the binding properties and stability of therapeutic peptides against enzymatic breakdown. This strategic incorporation is fundamental for crafting peptides with heightened efficacy and sustained action within living organisms driving innovation in therapeutic peptide design.

Neuroscience Research: Delving into the intricate realm of neurotransmitter regulation, MeD-Ala serves as a valuable tool for probing neurotoxicology and studying neurotransmitter systems like the glutamate receptor pathway. By investigating the effects of MeD-Ala on neurotransmission researchers unveil crucial insights into neurodegenerative disorders and potential therapeutic avenues shedding light on the complexities of brain function.

Analytical Standards: In the realm of analytical chemistry and mass spectrometry, Z-N-methyl-D-alanine emerges as a key reference compound that calibrates instruments and validates analytical methods to ensure precise measurement of related compounds. This application stands as a cornerstone for maintaining consistency and reliability in biochemical assays and quality control procedures underpinning the accuracy of analytical findings.

Protein Engineering: By introducing MeD-Ala into proteins, researchers unlock a realm of exploration into protein structure and function. This modified amino acid serves as a gateway to understanding the impact of methylation on protein folding stability and interactions illuminating the intricate dynamics of protein behavior. This knowledge is invaluable for unraveling protein complexities and engineering novel proteins tailored for industrial or therapeutic utilization fueling advancements in protein science.

1. Application of N-methyl-D-aspartate receptor nanopore in screening ligand molecules

Shu-Peng Li, Yong-Chao Zhang, Fang-Zhou Hu, Tharani Sabaretnam, Gilles J Guillemin, Ai-Hua Zou Bioelectrochemistry. 2020 Aug;134:107534. doi: 10.1016/j.bioelechem.2020.107534. Epub 2020 Apr 17.

N-methyl-D-aspartate receptors (NMDARs) are crucial for excitatory synaptic transmission in the central nervous system. To study NMDARs more accurately and conveniently, we developed a stable NMDAR nanopore in a planar lipid bilayer. Pharmacological properties were validated using the allosteric modulator Ro 25-6981 and antagonist D-2-amino-5-phosphonopentanoic acid (D-APV). The cyanotoxin β-N-methylamino-L-alanine (BMAA) found in fresh water systems is suspected to be associated with the development of neurodegenerative diseases. Therefore, BMAA and its two isomers L-2, 4-Diaminobutyric acid dihydrochloride (DAB) and N-(2-aminoethyl) glycine (AEG) and an endogenous excitotoxin, quinolinic acid (QA), were studied using the NMDAR nanopores to assess their effects on NMDAR modulation. We demonstrated that the NMDAR nanopore could reliably detect its ligand molecules at the single-channel level. The study also demonstrated the practicability of NMDAR nanopores, and results were validated using two-electrode voltage-clamp (TEVC) recording. Compared with TEVC recording, the NMDAR nanopores conducted ion channel gating at the single-channel level without being affected by other proteins on the cell membrane. The highly sensitive and accurate NMDAR nanopore technique thus has a unique advantage in screening NMDAR ligand molecules that could be associated with neurodegenerative disease.

2. Beta-N-methylamino-L-alanine in the presence of bicarbonate is an agonist at non-N-methyl-D-aspartate-type receptors

C N Allen, P S Spencer, D O Carpenter Neuroscience. 1993 Jun;54(3):567-74. doi: 10.1016/0306-4522(93)90228-8.

Beta-N-Methylamino-L-alanine, a component of the neurotoxic Cycas circinalis plant, activates an ionic current which is antagonized by extracellular Ca2+ but not by the excitatory amino acid receptor antagonists D,L-2-amino-5-phosphonovalerate (10-100 microM) or 6-cyano-7-nitroquinoxaline-2,3-dione (1-10 microM). This current was reduced by 50% in 0.5 mM extracellular Ca2+ and 92% in 3.0 mM Ca2+ when compared to those recorded in 0.1 mM Ca2+. Addition of 10 or 20 mM NaHCO3 to beta-N-methylamino-L-alanine (500 microM) potentiated the currents 224% and 578%, respectively. Addition of NaHCO3 to the extracellular Ringers (pH 7.2) shifted the pH to 7.7 (10 mM) or 8.3 (20 mM). beta-N-Methylamino-L-alanine was potentiated by NaHCO3 at pH 7.2, 7.7 and 8.3, but the potentiation with NaHCO3 (20 mM) was larger at pH 8.3 (5.7-fold) compared to pH 7.2 (3-fold). NaHCO3 (20 mM) had no effect on quisqualate-, N-methyl-D-aspartate- or kainate-activated ionic currents. The beta-N-methylamino-L-alanine-NaHCO3-activated currents were reduced 49% by 1 microM and 80% by 10 microM 6-cyano-7-nitroquinoxaline-2,3-dione suggesting an agonist action at non-N-methyl-D-aspartate-type receptors. Activity at N-methyl-D-aspartate receptors is unlikely since the beta-N-methylamino-L-alanine-NaHCO3 currents are not antagonized by D,L-2-amino-5-phosphonovalerate (10-100 microM), potentiated by addition of glycine (10 microM) or blocked by extracellular Mg2+.(ABSTRACT TRUNCATED AT 250 WORDS)