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79710

Sigma-Aldrich

O-Phospho-DL-serine

≥98.0% (NT), suitable for cell culture

Synonym(s):

DL-2-Amino-3-hydroxypropanoic acid 3-phosphate, DL-SOP, DL-Serine monophosphoric acid

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About This Item

Empirical Formula (Hill Notation):
C3H8NO6P
CAS Number:
17885-08-4
Molecular Weight:
185.07
Beilstein:
1726828
EC Number:
241-834-7
MDL number:
MFCD00021723
UNSPSC Code:
12352209
PubChem Substance ID:
57652815
NACRES:
NA.26

product name

O-Phospho-DL-serine, ≥98.0% (NT)

Assay

≥98.0% (NT)

form

powder or crystals

technique(s)

cell culture | mammalian: suitable

impurities

≤0.5% free serine (TLC)
≤1% water

color

white to faint beige

SMILES string

NC(COP(O)(O)=O)C(O)=O

InChI

1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)

InChI key

BZQFBWGGLXLEPQ-UHFFFAOYSA-N

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Related Categories

Biochem/physiol Actions

O-Phospho-DL-serine (pSer) is used in the study of non-enzymatic aminophospholipid glycation.
O-Phosphoserine is used in alternative pathways for biosynthesis of cysteine and of selenocysteine (Sec) by tRNA-dependent conversion of O-phosphoserine (Sep) by O-phosphoseryl-tRNA:selenocysteinyl-tRNA synthase (SepSecS).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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)

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Yoko Chiba et al.
The Journal of biological chemistry, 288(16), 11448-11458 (2013-03-13)
Novel-type serine-synthesizing enzymes, termed metal-independent phosphoserine phosphatases (iPSPs), were recently identified and characterized from Hydrogenobacter thermophilus, a chemolithoautotrophic bacterium belonging to the order Aquificales. iPSPs are cofactor-dependent phosphoglycerate mutase (dPGM)-like phosphatases that have significant amino acid sequence similarity to dPGMs
Po-Hsiang Wang et al.
The ISME journal, 13(4), 1042-1055 (2019-01-05)
Microbes in ecosystems often develop coordinated metabolic interactions. Therefore, understanding metabolic interdependencies between microbes is critical to deciphering ecosystem function. In this study, we sought to deconstruct metabolic interdependencies in organohalide-respiring consortium ACT-3 containing Dehalobacter restrictus using a combination of
Daniel Agren et al.
The Journal of biological chemistry, 283(46), 31567-31574 (2008-09-19)
The biosynthesis of cysteine is a crucial metabolic pathway supplying a building block for de novo protein synthesis but also a reduced thiol as a component of the oxidative defense mechanisms that appear particularly vital in the dormant state of
Yuhei Araiso et al.
Nucleic acids research, 36(4), 1187-1199 (2007-12-26)
The micronutrient selenium is present in proteins as selenocysteine (Sec). In eukaryotes and archaea, Sec is formed in a tRNA-dependent conversion of O-phosphoserine (Sep) by O-phosphoseryl-tRNA:selenocysteinyl-tRNA synthase (SepSecS). Here, we present the crystal structure of Methanococcus maripaludis SepSecS complexed with
Seong-Jun Kim et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(17), 6413-6418 (2014-04-16)
Mitochondrial dynamics is crucial for the regulation of cell homeostasis. Our recent findings suggest that hepatitis C virus (HCV) promotes Parkin-mediated elimination of damaged mitochondria (mitophagy). Here we show that HCV perturbs mitochondrial dynamics by promoting mitochondrial fission followed by
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