M6635

N-(2-Mercaptopropionyl)glycine

• Synonym(s): Tiopronin
• Linear Formula: CH₃CH(SH)CONHCH₂COOH
• CAS Number: 1953-02-2
• Molecular Weight: 163.19
• NACRES: NA.26
• PubChem Substance ID: 24897101
• eCl@ss: 32160406
• UNSPSC Code: 12352209
• EC Number: 217-778-4
• MDL number: MFCD00004861
• Beilstein/REAXYS Number: 1859822

Properties

• assay: ≥98% (TLC)
• Quality Segment: 100
• form: powder
• color: white
• mp: 98-100 °C
• application(s): cell analysis; peptide synthesis
• SMILES string: CC(S)C(=O)NCC(O)=O
• InChI: 1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8)
• InChI key: YTGJWQPHMWSCST-UHFFFAOYSA-N

Description

Application

N-(2-Mercaptopropionyl)glycine or Tiopronin has been used:

• in the preparation of polyethylenimine (PEI)-coated gold microparticles (PEI-gold) for biolistic delivery of nucleic acids[1]
• to study the role of reactive oxygen species (ROS) at the reperfusion stage in in vivo isoflurane preconditioning-induced neuroprotection[2]
• as a ROS inhibitor to study its effect on lysophosphatidylcholine (LPC)-induced inflammasome activation[3]

Biochem/physiol Actions

N-(2-Mercaptopropionyl)glycine (NMPG) is a thiol compound associated with autoimmune hypoglycemia. It is a diffusible antioxidant and reduces the severity of colonic injury. NMPG also relieves myeloperoxidase activity and stimulates hypoxia-inducible factor-1 (HIF-1) - vascular endothelial growth factor (VEGF) pathway for ulcer healing.[4]

N-(2-Mercaptopropionyl)glycine is a free radical scavenger.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• pcodes: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves