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H9633

Sigma-Aldrich

L-Homocysteic acid

≥98% (TLC)

Synonym(s):

L-2-Amino-4-sulfobutyric acid

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About This Item

Empirical Formula (Hill Notation):
C4H9NO5S
CAS Number:
14857-77-3
Molecular Weight:
183.18
MDL number:
MFCD00066018
UNSPSC Code:
12352106
PubChem Substance ID:
24895863
NACRES:
NA.32

product name

L-Homocysteic acid, ≥95%

assay

≥95%
≥98% (TLC)

form

powder

color

white to off-white

application(s)

cell analysis

SMILES string

N[C@@H](CCS(O)(=O)=O)C(O)=O

InChI

1S/C4H9NO5S/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H,8,9,10)/t3-/m0/s1

InChI key

VBOQYPQEPHKASR-VKHMYHEASA-N

Application

L-Homocysteic acid has been used to study hydrogen peroxide-mediated changes in physiological and pathological conditions in the nervous system.

Biochem/physiol Actions

L-Homocysteic acid (L-HCA) is an endogenous neurotransmitter ligand of NMDA (N-methyl-D-aspartate) receptors. It is an analog of glutamate and competitively suppresses glutamate-cystine (xc-) antiporter function in neurons, causing decrease in cysteine uptake.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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R Gurke et al.
Journal of pharmaceutical and biomedical analysis, 174, 578-587 (2019-07-02)
The role of homocysteic acid (HCA) in severe diseases like Alzheimer's disease is under discussion and some recent studies correlate elevated HCA concentrations with the diagnosis of Alzheimer's. However, non-selective and insufficiently sensitive methods have been used to quantitate HCA
T Knöpfel et al.
Neuroscience letters, 81(1-2), 188-192 (1987-10-16)
The effects of ionophoretically applied L-homocysteate (L-HCA), L-glutamate (L-Glu) and N-methyl-D-aspartate (NMDA) were compared in rat neocortical neurons recorded intracellularly in vitro. The firing pattern and the time course of membrane depolarization induced by L-HCA resembled those of NMDA responses.
Itopa E Ajayi et al.
Respiratory physiology & neurobiology, 252-253, 18-27 (2018-03-20)
Changes in cardiorespiratory control accompany the expression of complex emotions, indicative of limbic brain inputs onto bulbar autonomic pathways. Previous studies have focussed on the role of the prefrontal cortex in autonomic regulation. However, the role of the hippocampus, also
Danté T Johnson et al.
The Journal of biological chemistry, 294(32), 11969-11979 (2019-07-03)
Fast photochemical oxidation of proteins (FPOP) is a MS-based method that has proved useful in studies of protein structures, interactions, conformations, and protein folding. The success of this method relies on the irreversible labeling of solvent-exposed amino acid side chains
J W Olney et al.
Brain research bulletin, 19(5), 597-602 (1987-11-01)
L-Homocysteic acid (L-HCA) has been proposed as a natural transmitter at the N-methyl-D-aspartate (NMDA) subtype of excitatory amino acid receptor based on recent evidence that L-HCA occurs L-HCA occurs naturally in the mammalian CNS, is released from K+ stimulated brain
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