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B107

Sigma-Aldrich

L-BMAA hydrochloride

≥97% (NMR), powder

Synonym(e):

S(+)-2-Amino-3-(methylamino)propionic acid hydrochloride

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About This Item

Empirische Formel (Hill-System):
C4H10N2O2 · HCl
CAS-Nummer:
16012-55-8
Molekulargewicht:
154.60
MDL-Nummer:
MFCD00055227
UNSPSC-Code:
12352209
PubChem Substanz-ID:
329773160
NACRES:
NA.32

Qualitätsniveau

100

Assay

≥97% (NMR)

Form

powder

Optische Aktivität

[α]/D +21 to +31°, c = 0.5 M in 0.1 M HCl(lit.)

Lagerbedingungen

desiccated

Farbe

white to beige

Löslichkeit

H2O: soluble (solutions may be stored for several days at 4 °C)

Lagertemp.

−20°C

SMILES String

Cl.CNC[C@H](N)C(O)=O

InChI

1S/C4H10N2O2.ClH/c1-6-2-3(5)4(7)8;/h3,6H,2,5H2,1H3,(H,7,8);1H/t3-;/m0./s1

InChIKey

VDXYGASOGLSIDM-DFWYDOINSA-N

Allgemeine Beschreibung

L-BMAA hydrochloride/β-N-methylamino-l-alanine (BMAA) is a cyanobacterial neurotoxin.

Anwendung

L-BMAA hydrochloride has been used as a standard to compare all the samples in the analysis of β-N-methylamino-l-alanine (BMAA) isomers in desert crust material. It has also been used as an additive with f/2+Si medium to treat the cells of Phaeodactylum tricornutum and Thalassiosira weissflogii to study its effect on them.

Biochem./physiol. Wirkung

L-BMAA hydrochloride helps to block the addition of heparan sulfate to glypican-1. It possesses unusual glutamate receptor binding properties. It may cause amyotrophic lateral sclerosis/Lou Gehrig′s disease.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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Neurotoxic amino acids and their isomers in desert environments
Metcalf JS, et al.
Journal of arid environments, 140-144 (2015)
David A Davis et al.
Journal of neuropathology and experimental neurology, 79(4), 393-406 (2020-02-23)
The early neuropathological features of amyotrophic lateral sclerosis/motor neuron disease (ALS/MND) are protein aggregates in motor neurons and microglial activation. Similar pathology characterizes Guamanian ALS/Parkinsonism dementia complex, which may be triggered by the cyanotoxin β-N-methylamino-l-alanine (BMAA). We report here the
Olga A Koksharova et al.
Toxins, 12(6) (2020-06-10)
All cyanobacteria produce a neurotoxic non-protein amino acid β-N-methylamino-L-alanine (BMAA). However, the biological function of BMAA in the regulation of cyanobacteria metabolism still remains undetermined. It is known that BMAA suppresses the formation of heterocysts in diazotrophic cyanobacteria under nitrogen
2-Amino-β-methylamino-propionc acid, a new amino acid from seeds of Cycas circinali.
Vega, et al.
Psychochemistry, 6, 759-762 (1967)
Johan Eriksson et al.
Amino acids, 36(1), 43-48 (2008-01-12)
Two different assays have been developed and used in order to investigate the optimal conditions for derivatization and detection of acid beta-N-methyl-amino-L-alanine (BMAA) in a cyanobacterial sample. BMAA was extracted from cyanobacterial cultures both from the cytosolic ("free") fraction and
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