ChemicalBook CAS DataBase List 31828-68-9

31828-68-9

Name	L-HOMOCYSTEINE THIOLACTONE HYDROCHLORIDE
CAS	31828-68-9
EINECS(EC#)	250-824-1
Molecular Formula	C4H8ClNOS
MDL Number	MFCD00065494
Molecular Weight	153.63
MOL File	31828-68-9.mol

Synonyms

H-HOCYS-THIOLACTONE HCL L-HOMOCYSTEINETHIOLACTONEHCL -3-Aminodihydrothiophen-2(3H) L-HOMOCYSTEINE THIOLACTONE HCL*CRYST L-HOMOCYSTEINETHILOACTONEHYDROCHLORIDE L-HOMOCYSTEINE THIOLACTONE HYDROCHLORIDE L-HOMOCYSTEINE THIOLACTONE HCL*CRYSTALLI NE (S)-3-aminodihydrothiophen-2(3H)-one hydrochloride CAindexname:2(3H)-Thiophenone,3-aminodihydro-,hydr (S)-3-Aminodihydro-2(3H)-thiophenone hydrochloride L-HOMOCYSTEINE THIOLACTONE HYDROCHLORIDE ULTRA-PURE 2(3H)-THIOPHENONE, 3-AMINODIHYDRO-, HYDROCHLORIDE, L- 2(3H)-THIOPHENONE, 3-AMINODIHYDRO-, HYDROCHLORIDE, (S)- 2(3H)-THIOPHENONE, 3-AMINODIHYDRO-, HYDROCHLORIDE, (3S)- L-2-AMINO-4-MERCAPTOBUTYRIC ACID 1,4-THIOLACTONE HYDROCHLORIDE L-Homocysteine thiolactone hydrochloride,L-2-Amino-4-mercaptobutyric acid 1,4-thiolactone hydrochloride

Chemical Properties

Appearance	Colourless solid
Melting point	185-191 °C
storage temp.	2-8°C
solubility	Aqueous Acid (Slightly), DMSO (Slightly), Water (Slightly)
form	Solid
color	Pale Beige
BRN	3911455
Stability:	Hygroscopic
Major Application	detection peptide synthesis
InChI	1S/C4H7NOS.ClH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H/t3-;/m0./s1
InChIKey	ZSEGSUBKDDEALH-DFWYDOINSA-N
SMILES	Cl[H].N[C@H]1CCSC1=O

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302-H315-H319-H335
Precautionary statements	P280-P305+P351+P338
Safety Statements	22-24/25 less more
WGK Germany	3
F	1-8-9
Storage Class	11 - Combustible Solids

Hazard Information

Chemical Properties

Colourless solid

Uses

L-Homocysteine Thiolactone Hydrochloride is used to prepare substituted homocysteine analogs as inhibitors of peptidylglycine α-amidating monooxygenase. It is also used to synthesize (mercaptoacyl)alanylprolines as metalloprotease inhibitors.

Biochem/physiol Actions

L-Homocysteine thiolactone, an amine reactive agent, is used to study post-translational modification of proteins, especially at lysine residues.

in vivo

L-Homocysteine thiolactone hydrochloride can be used to create models of hyperhomocysteinemia^[2].

Induction of Hyperhomocysteinemia (HHcy)^[2]^[3]

Background

Homocysteine (Hcy) is an amino acid that requires vitamins B12 and folic acid for its metabolism. Vitamins B12 and folic acid deficiencies lead to hyperhomocysteinemia (HHcy, elevated Hcy), which is linked to the development of diabetic retinopathy (DR), age-related macular degeneration (AMD), and Alzheimer’s disease (AD).

Specific Modeling Methods

Male C57Mice: cbs^+/-; 3-5 weeks ? C57BL6/J; 6-8 weeks of age
Administration: 1 μL ? intravitreally ? 200 μM BL/6 mice (5 weeks old)

Note

(1) To avoid uncontrolled intraocular pressure increase, the volume of intravitreal injections is limited to 1 μL.
(2) L-Homocysteine thiolactone hydrochloride is dissolved in water and a working solution of 10x is prepared by diluting 1 μL of stock solution (200 mM) to 100 μL with PBS. Then by injecting 1 μL of this working solution, 200 μM vitreal concentration of Hcy-thiolactone is obtained.

Modeling Indicators

Molecular changes: Caused microglia activation in the retina. Increased indicators: pro-inflammatory cytokines IP-10, TNFα, IL-1β, and IL6

Correlated Product(s): L-Homocysteine (HY-W010347)

Opposite Product(s): /

Animal Model:	cbs^+/- mice and normal wild type mice (C57BL6/J), 6-8 weeks of age^[2]
Dosage:	1 μL; 200 μM
Administration:	Intravitreally
Result:	Normal retinal flat-mount preparations from cbs^+/+ mice showed quiescent ramified microglia, while cbs^-/- and cbs^+/- retinas demonstrated rod-like microglia devoid of branching processes, indicating microglia activation in HHcy mice.

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