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S4503

Sigma-Aldrich

DL-Serine hydroxamate

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

Synonyme(s) :

SHX

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About This Item

Formule empirique (notation de Hill):
C3H8N2O3
Numéro CAS:
55779-32-3
Poids moléculaire :
120.11
Numéro MDL:
MFCD00055712
Code UNSPSC :
12352209
ID de substance PubChem :
24899606
Nomenclature NACRES :
NA.26

product name

DL-Serine hydroxamate, seryl-tRNA synthetase inhibitor

Pureté

≥97% (TLC)

Forme

powder

Technique(s)

ligand binding assay: suitable

Couleur

white to off-white

Application(s)

cell analysis

Température de stockage

−20°C

Chaîne SMILES 

NC(CO)C(=O)NO

InChI

1S/C3H8N2O3/c4-2(1-6)3(7)5-8/h2,6,8H,1,4H2,(H,5,7)

Clé InChI

LELJBJGDDGUFRP-UHFFFAOYSA-N

Catégories apparentées

Application

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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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G P van Wezel et al.
Microbiology (Reading, England), 141 ( Pt 10), 2519-2528 (1995-10-01)
In Streptomyces coelicolor A3(2), two genes, tuf1 and tuf3, encode the apparent polypeptide chain elongation factors EF-Tu1 and EF-Tu3, respectively. While tuf1 appears to code for the major EF-Tu, the function of tuf3 is unknown. To assess the role of
B Belitsky et al.
The Journal of biological chemistry, 257(9), 4677-4679 (1982-05-10)
Lack of three different amino acids or treatment with the analogue DL-serine hydroxamate does not induce the accumulation of ppGpp and pppGpp, the 3'-pyrophosphates of GDP and GTP, respectively, in Rhizobium meliloti strain 41. Surprisingly, RNA accumulation is controlled under
Effect of serine hydroxamate on phospholipid synthesis in Escherichia coli.
Pizer Ll and Merlie JP
Journal of Bacteriology, 114(3) (1973)
Yu Zeng et al.
Antimicrobial agents and chemotherapy, 53(11), 4619-4627 (2009-09-02)
The Trojan horse antibiotic albomycin, produced by Streptomyces sp. strain ATCC 700974, contains a thioribosyl nucleoside moiety linked to a hydroxamate siderophore through a serine residue. The seryl nucleoside structure (SB-217452) is a potent inhibitor of seryl-tRNA synthetase (SerRS) in
Yuki Matsumoto et al.
BMC genomics, 14, 808-808 (2013-11-21)
Cell growth rate reflects an organism's physiological state and largely relies on the ability of gene expression to respond to the environment. The relationship between cellular growth rate and gene expression remains unknown. Growth rate-coordinated changes in gene expression were
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