S4503

DL-Serine hydroxamate

≥97% (TLC), suitable for ligand binding assays

• Synonym(s): SHX
• Empirical Formula (Hill Notation): C₃H₈N₂O₃
• CAS Number: 55779-32-3
• Molecular Weight: 120.11
• UNSPSC Code: 12352209
• PubChem Substance ID: 24899606
• NACRES: NA.26
• MDL number: MFCD00055712

Properties

• Product Name: DL-Serine hydroxamate, seryl-tRNA synthetase inhibitor
• Quality Segment: 200
• assay: ≥97% (TLC)
• form: powder
• technique(s): ligand binding assay: suitable
• color: white to off-white
• application(s): cell analysis
• storage temp.: −20°C
• SMILES string: NC(CO)C(=O)NO
• InChI: 1S/C3H8N2O3/c4-2(1-6)3(7)5-8/h2,6,8H,1,4H2,(H,5,7)
• InChI key: LELJBJGDDGUFRP-UHFFFAOYSA-N

Description

Application

Serine has been used as an inhibitor of seryl-tRNA synthetase.[1][2] DL-Serine hydroxamate is used to induce metabolic synthesis of guanosine 3′-diphosphate 5′-diphosphate (ppGpp) in E. coli by amino acid starvation.[3] It is also used to synchronize cell cycle in E. coli cultures by inhibition of tRNA charging.[4]

Biochem/physiol Actions

Serine is involved in the one-carbon unit metabolism. It is associated with the biosynthesis of cysteine, ceramide, phosphatidylserine, purine and pyrimidine. In bacteria, it participates in tryptophan synthesis. Gluconeogenesis, one of the important biochemical processes, involves serine, particularly in ruminants. Protein phosphorylation is one such event that utilizes serine. Glycine, a metabolic product of serine, serves as an antioxidant and a neurotransmitter. D-serine is known to activate the N-methyl-D-aspartate (NMDA) receptors of the brain. Serine hydroxamate, a structural analogue of serine prevents seryl-tRNA (transfer ribonucleic acid) charging and thereby decreases phospholipid and nucleic acid synthesis in Escherichia coli.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)