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S4503

Sigma-Aldrich

DL-Serine hydroxamate

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

Synonym(s):

SHX

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About This Item

Empirical Formula (Hill Notation):
C3H8N2O3
CAS Number:
Molecular Weight:
120.11
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26

product name

DL-Serine hydroxamate, seryl-tRNA synthetase inhibitor

Quality Level

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

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.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D Riesenberg et al.
Journal of general microbiology, 130(10), 2549-2558 (1984-10-01)
The accumulation of RNA and protein and the kinetics of nucleoside triphosphate and guanosine polyphosphate pools during amino acid starvation and carbon source downshift were investigated in Streptomyces hygroscopicus. RNA accumulation was controlled stringently during both amino acid starvation and
M P Patricelli et al.
Proteomics, 1(9), 1067-1071 (2002-05-07)
The field of biochemistry is currently faced with the enormous challenge of assigning functional significance to more than thirty thousand predicted protein products encoded by the human genome. In order to accomplish this daunting task, methods will be required that
David L Erickson et al.
Infection and immunity, 72(10), 5638-5645 (2004-09-24)
The stringent response is a mechanism by which bacteria adapt to nutritional deficiencies through the production of the guanine nucleotides ppGpp and pppGpp, produced by the RelA enzyme. We investigated the role of the relA gene in the ability of
Daniel J Ferullo et al.
PLoS genetics, 4(12), e1000300-e1000300 (2008-12-17)
The bacterial stringent response, triggered by nutritional deprivation, causes an accumulation of the signaling nucleotides pppGpp and ppGpp. We characterize the replication arrest that occurs during the stringent response in Escherichia coli. Wild type cells undergo a RelA-dependent arrest after
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

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