All Photos(4)

H9633

Sigma-Aldrich

L-Homocysteic acid

Synonym(s):
L-2-Amino-4-sulfobutyric acid
Empirical Formula (Hill Notation):
C4H9NO5S
CAS Number:
Molecular Weight:
183.18
MDL number:
PubChem Substance ID:
NACRES:
NA.32

assay

≥98% (TLC)

Quality Level

form

powder

application(s)

cell analysis: suitable

color

white to off-white

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

Related Categories

Application

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

Packaging

1 g in poly bottle
25, 100, 250 mg in poly bottle

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H9633.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Hari H Subramanian et al.
The Journal of comparative neurology, 526(2), 229-242 (2017-09-07)
The nucleus retroambiguus (NRA) is a neuronal cell group in the medullary ventrolateral tegmentum, rostrocaudally between the obex and the first cervical spinal segment. NRA neurons are premotor interneurons with direct projections to the motoneurons of soft palate, pharynx, and...
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...
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...
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....
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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