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P7769

Sigma-Aldrich

1,2-Diacyl-sn-glycero-3-phospho-L-serine

from bovine brain, ≥97% (TLC), amorphous powder, structural phospholipid

Synonym(s):

3-sn-Phosphatidyl-L-serine, L-α-Phosphatidyl-L-serine, PS, Phosphatidylserine

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About This Item

UNSPSC Code:
12352200
NACRES:
NA.77

product name

1,2-Diacyl-sn-glycero-3-phospho-L-serine, ≥97% (TLC), from bovine brain, amorphous powder

biological source

bovine brain

Assay

≥97% (TLC)

form

amorphous powder

storage temp.

−20°C

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Application

1,2-Diacyl-sn-glycero-3-phospho-L-serine has been used:
  • as a lipid standard in time-of-flight secondary ion mass spectrometry (ToF-SIMS) spectral fingerprints
  • as a reference standard in thin layer chromatography (TLC) for quantifying lipids from astrocyte-conditioned media (ACM) treated fibroblasts
  • as a component of large unilamellar vesicles for annexin A2 aggregation studies

Biochem/physiol Actions

1,2-Diacyl-sn-glycero-3-phospho-L-serine or phosphatidylserine (PS) is a structurally diverse acidic phospholipid having fatty acid ester at the glycerol sn positions. Bovine brain cortex based PS is a potent brain nutrient. It favors neurotransmission and may improve memory in dementia. PS is also the major membrane phospholipid associated with the nuclear membrane, myelin, endoplasmic reticulum, Golgi and mitochondria. The synthesis of PS is catalyzed by phosphatidylserine synthase 1 from L-serine and CDP-diacylglycerol in the mitochondria-associated membrane (MAM) domains of the endoplasmic reticulum. PS is externalized during phagocytosis and is dysregulated in tumors making it a potential marker for therapeutic targeting.
A slowly metabolized structural phospholipid found mainly in gray matter.

Features and Benefits

This compound is featured on the Phospholipase D and PKC pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Caution

Solutions exposed to room temperature will decompose about 0.5% per day.

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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Regulation of the equilibrium between closed and open conformations of annexin A2 by N-terminal phosphorylation and S100A4-binding
Ecsedi P, et al.
Structure, 25(8), 1195-1207 (2017)
Thorsten Keller et al.
Molecular pharmacology, 95(2), 169-182 (2018-11-10)
Organic cation transporters OCT1 (SLC22A1) and OCT2 (SLC22A2) are critically involved in absorption and excretion of diverse cationic drugs. Because drug-drug interactions at these transporters may induce adverse drug effects in patients, in vitro testing during drug development for interaction
Phosphatidylserine is a global immunosuppressive signal in efferocytosis, infectious disease, and cancer
Birge RB, et al.
Cell Death and Differentiation, 23(6), 962-962 (2016)
Formation and function of phosphatidylserine and phosphatidylethanolamine in mammalian cells
Vance JE and Tasseva G
Biochimica et biophysica acta. General subjects, 1831(3), 543-554 (2013)
Comparison of molecular species of various transphosphatidylated phosphatidylserine (PS) with bovine cortex PS by mass spectrometry
Chen S and Li KW
Chemistry and Physics of Lipids, 152(1), 46-56 (2008)
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