Z-N-methyl-L-alanine
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Z-N-methyl-L-alanine

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Category
CBZ-Amino Acids
Catalog number
BAT-003395
CAS number
21691-41-8
Molecular Formula
C12H15NO4
Molecular Weight
237.20
Z-N-methyl-L-alanine
IUPAC Name
(2S)-2-[methyl(phenylmethoxycarbonyl)amino]propanoic acid
Synonyms
Z-N-Me-L-Ala-OH; Cbz-N-methyl-L-alanine; Z-L-MEALA-OH; N-methyl-N-Cbz-L-alanine; L-N-benzyloxycarbonyl-N-methylalanine; N-phenylmethoxycarbonyl-N-methyl-L-alanine
Appearance
White to off-white powder
Purity
98-100% (HPLC)
Density
1.222 g/cm3
Melting Point
54-56 °C
Boiling Point
389.5±31.0 °C
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-/m0/s1
InChI Key
QGEQKVZQPWSOTI-VIFPVBQESA-N
Canonical SMILES
CC(C(=O)O)N(C)C(=O)OCC1=CC=CC=C1

Z-N-methyl-L-alanine, a specialized amino acid of significance in biochemical research and pharmaceutical development, is explored in various applications with high perplexity and burstiness:

Neurotoxicity Studies: Delving into neurotoxicity investigations, Z-N-methyl-L-alanine emerges as a key player in probing the effects of non-protein amino acids on neural cells. Scientists leverage this compound to unravel its impact on neural pathways, offering insights into neurodegenerative ailments like ALS and Alzheimer's. Through these inquiries, potential therapeutic strategies are sought to combat neurotoxicity.

Enzyme Inhibition Research: Positioned as an essential asset in exploring enzyme inhibition mechanisms, Z-N-methyl-L-alanine aids researchers in dissecting how it interacts with specific enzymes. This interaction sheds light on enzyme functionality and inhibition kinetics, crucial for crafting novel inhibitors with pharmaceutical potential.

Peptide Synthesis: Within peptide synthesis, Z-N-methyl-L-alanine finds utility in introducing methylated amino acid residues, enhancing peptides' stability and affinity towards target molecules. This modification greatly benefits the development of therapeutic peptides and advances biomolecular research.

Biomarker Discovery: Unveiling its role in biomarker discovery, Z-N-methyl-L-alanine facilitates the identification and validation of biomarkers across various diseases. Through analytical methods, researchers quantify this compound in biological samples, correlating its presence with disease states or progression. This strategy aids in developing diagnostic tools and elucidating the role of disease biomarkers in pathogenesis.

1. N,N'-[(8-endo,11-endo-Dihy-droxy-penta-cyclo-[5.4.0.0.0.0]undecane-8,11-di-yl)bis-(methyl-enecarbon-yl)]di-l-phenyl-alanine
Rajshekhar Karpoormath, Patrick Govender, Hendrik G Kruger, Thavendran Govender, Glenn E M Maguire Acta Crystallogr Sect E Struct Rep Online. 2010 Sep 11;66(Pt 10):o2537-8. doi: 10.1107/S1600536810035956.
The title compound, C(33)H(36)N(2)O(8), is the first example of a disubstituted peptidic pentacycloundecane (PCU) diol. The structure displays an array of inter- and intra-molecular hydrogen bonding by both amide and alcohol functional groups. This hydrogen-bonding system connects the mol-ecules into a three-dimensional network.
2. β-N-Methyl-Amino-L-Alanine cyanotoxin promotes modification of undifferentiated cells population and disrupts the inflammatory status in primary cultures of neural stem cells
Sarah Méresse, et al. Toxicology. 2022 Dec;482:153358. doi: 10.1016/j.tox.2022.153358. Epub 2022 Oct 27.
β-N-Methyl-Amino-L-Alanine (BMAA) produced by 95% of cyanobacteria is in constant augmentation with cyanobacteria worldwide proliferation due to global warming and eutrophication. Previously, it has been shown that this contaminant induced neurological disorders, notably by acting as a developmental toxin. However, very few studies focus on the impact of BMAA on neuroglial cells, like astrocytes and microglial cells, in a developmental context. In the present study, we investigated whether BMAA disturbs neurogenesis from mice subventricular zone (SVZ) cells and whether this neurotoxin induces neuroinflammation. We show that BMAA at 100 µM disturbs the population of undifferentiated cells (B1 and C cells) and promotes their proliferation. Further, BMAA affects the organization of neuroblasts, indicating that SVZ function could be impaired. BMAA affects neuroinflammatory processes by increasing the release of proinflammatory cytokines IL-1β, IL-6 and TNFα. Our study adds to evidence that BMAA may disturb the central nervous system homeostasis by targeting glial cells. We highlighted that BMAA may impair SVZ niches and drives astrocytes and microglial cells into a proinflammatory status, with an ameboid shape for microglia.
3. N-Cinnamoyl-l-phenyl-alanine methyl ester
Laurent F Bornaghi, Sally-Ann Poulsen, Peter C Healy, Alan R White Acta Crystallogr Sect E Struct Rep Online. 2007 Dec 6;64(Pt 1):o139. doi: 10.1107/S1600536807055973.
As part of an ongoing investigation into the development of N-substituted amino acids as building blocks for dynamic combinatorial chemistry, we report the structure of the title compound, C(19)H(19)NO(3). This compound crystallizes as discrete mol-ecules. The cinnamoyl group is non-planar, with the phenyl ring and the amide twisted out of the ethyl-ene plane. The benzyl and ester groups lie above and below the amide plane. The mol-ecules stack along the crystallographic c axis, connecting through C(4) chains of N-H⋯O hydrogen bonds, with the extended structure stabilized by C-H⋯O inter-actions and π-π inter-actions [centroid-to-centroid distances 3.547 (8) and 3.536 (8) Å].
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