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
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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