DL-O-Phosphoserine NEW

DL-O-Phosphoserine is the racemic mixture (equal parts D- and L-enantiomers) of the phosphorylated form of the amino acid serine. Here's a detailed breakdown:

1. Chemical Structure & Identity

• Core Structure: Serine (an α-amino acid) with a phosphate group esterified to its side-chain hydroxyl group (−CH₂OPO₃H₂).

• DL Prefix: Indicates the racemic (50:50) mix of D-phosphoserine and L-phosphoserine enantiomers.

• Systematic Name: 2-Amino-3-phosphonoxypropanoic acid.

• Molecular Formula: C₃H₈NO₆P.

2. Biological Significance

• Phosphoserine in Nature:

• Reversible phosphorylation of serine residues in proteins regulates cellular signaling (e.g., kinase/phosphatase pathways).

• Generated during serine biosynthesis (from 3-phosphoglycerate).

• Precursor to L-serine (dephosphorylation) and cysteine (via cystathionine).

• L-O-Phosphoserine (the natural enantiomer) is a key metabolic intermediate:

• Post-Translational Modification (PTM):

3. DL vs. L-Phosphoserine

• L-O-Phosphoserine: Biologically active form involved in metabolism and PTMs.

• DL-O-Phosphoserine:

• Synthetic racemate – not naturally occurring.

• Primarily used as a research reagent or biochemical tool.

• Cheaper/easier to synthesize than enantiopure L-form.

4. Key Applications & Uses

• Biochemical Research:

• Substrate/inhibitor for phosphatases, kinases, or serine-metabolizing enzymes.

• Studying phosphoamino acid metabolism.

• Cell Culture:

• Component of some serum-free media (e.g., for neuronal or stem cells) as a phosphate donor.

• Buffers:

• Used in electrophoresis or chromatography buffers due to its zwitterionic properties.

• Peptide Synthesis:

• Building block for synthesizing phosphopeptides (though L-form is preferred for biological studies).

5. Properties

• Solubility: Highly soluble in water; insoluble in organic solvents.

• Stability:

• Sensitive to heat/acidic conditions → may hydrolyze to serine + phosphate.

• Store at −20°C in dry form.

• Isoelectric Point (pI): ~3.5–4.0 (due to phosphate group’s low pKa).