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H6010

Sigma-Aldrich

L-Homocystine

≥98% (HPLC)

Synonym(s):

L-4,4′-Dithiobis(2-aminobutanoic acid)

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About This Item

Empirical Formula (Hill Notation):
C8H16N2O4S2
CAS Number:
626-72-2
Molecular Weight:
268.35
Beilstein/REAXYS Number:
1728583
EC Number:
210-962-5
MDL number:
MFCD00020391
UNSPSC Code:
12352209
PubChem Substance ID:
24895724
NACRES:
NA.26

product name

L-Homocystine, ≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

color

white to off-white

mp

281-284 °C (dec.) (lit.)

application(s)

cell analysis
peptide synthesis

SMILES string

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

InChI

1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14)/t5-,6-/m0/s1

InChI key

ZTVZLYBCZNMWCF-WDSKDSINSA-N

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Biochem/physiol Actions

L-Homocystine is the oxidized member of the L-homocysteine:L-homocystine pair. Homocysteine/homocystine is derived from methionine. Homocysteine is a pro-thrombotic factor, vasodilation impairing agent, pro-inflammatory factor and endoplasmatic reticulum-stress inducer used to study cardiovascular disease mechanisms.

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)

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S Ramakrishnan et al.
Indian journal of biochemistry & biophysics, 43(5), 275-283 (2006-12-01)
The amino acid homocysteine (Hcy), formed from methionine has profound importance in health and diseases. In normal circumstances, it is converted to cysteine and partly remethylated to methionine with the help of vit B12 and folate. However, when normal metabolism
Camila Simioni Vanzin et al.
Molecular genetics and metabolism, 104(1-2), 112-117 (2011-07-12)
Homocystinuria is an inherited disorder biochemically characterized by high urinary excretion of homocystine and increased levels of homocysteine (Hcy) and methionine in biological fluids. Affected patients usually have a variety of clinical and pathologic manifestations. Previous experimental data have shown
Geoffrey P McDermott et al.
Analytical chemistry, 83(15), 6034-6039 (2011-07-08)
The quantification of low-molecular mass thiols and disulfides involved in cellular redox processes is hindered by oxidation or degradation of analytes during conventional sample preparation steps (including deproteinization and derivatization). Researchers therefore seek techniques that minimize sample handling and permit
J Perła-Kaján et al.
Amino acids, 32(4), 561-572 (2007-02-08)
Homocysteine, a non-protein amino acid, is an important risk factor for ischemic heart disease and stroke in humans. This review provides an overview of homocysteine influence on endothelium function as well as on protein metabolism with a special respect to
Karin J A Lievers et al.
Annals of clinical biochemistry, 40(Pt 1), 46-59 (2003-01-25)
Homocysteine, a sulphur amino acid, is a branch-point intermediate of methionine metabolism. It can be degraded in the transsulphuration pathway to cystathionine, or remethylated to methionine via the remethylation pathway. In both pathways, major genetic defects that cause enzyme deficiencies
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