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Serine

C3H7NO3 organic

Properties

StateSolid (white crystalline powder)
ColorWhite
SolubilityHighly soluble in water (362 g/L at 25°C); insoluble in ethanol
Melting Point246°C (decomposes)
Boiling PointDecomposes before boiling

About Serine

Serine is a small polar amino acid with the formula C3H7NO3 and a molar mass of 105.093 g/mol. It's classified as non-essential because mammals synthesize it from glycine, threonine, or the glycolytic intermediate 3-phosphoglycerate via the phosphoserine pathway, but the metabolic load it carries is enormous out of proportion to its size. The hydroxyl side chain is the substrate for the largest single class of post-translational modifications in eukaryotes: serine phosphorylation by Ser/Thr kinases such as PKA, PKC, CDK, and the MAPK family generates an estimated 80 percent of the phosphoproteome and is the primary on/off switch for cell-cycle progression, metabolic enzyme activity, and signal transduction. The same hydroxyl serves as the nucleophile in the Ser-His-Asp catalytic triad of serine proteases — trypsin, chymotrypsin, elastase, thrombin, and the entire blood-coagulation cascade — where the activated serine alkoxide attacks the substrate carbonyl to form a transient acyl-enzyme intermediate. Serine is also the point of entry to one-carbon metabolism via serine hydroxymethyltransferase, which transfers serine's beta-carbon to tetrahydrofolate to make 5,10-methylene-THF, the carbon donor for thymidylate synthase and thus the dependency that 5-fluorouracil chemotherapy exploits. Serine was first isolated in 1865 from sericin, a silk protein, which gave it its name from Latin sericum.

Where you'll encounter it

If you've ever taken a phosphatase inhibitor cocktail (sodium fluoride, beta-glycerophosphate, sodium orthovanadate) when lysing cells for a Western blot, you were trying to preserve the phosphoserine and phosphothreonine signals that would otherwise be hydrolyzed in minutes by endogenous PP1 and PP2A phosphatases — that's how dynamic Ser phosphorylation actually is in a live cell. In an oncology research lab, the serine biosynthesis pathway has become a hot drug target: many cancers upregulate phosphoglycerate dehydrogenase (PHGDH) to feed both serine synthesis and one-carbon flux into nucleotide production, and PHGDH inhibitors like NCT-503 are in preclinical development. Outside the lab, you'll find serine in the natural moisturizing factor (NMF) of skin — about 12 percent of the free amino-acid pool in the stratum corneum is serine, which is why hydrolyzed silk-protein extracts show up on cosmetic ingredient lists targeted at dry-skin formulations.

Common Uses

  • Substrate for Ser/Thr kinase phosphorylation studies in cell signaling research
  • Nucleophile in the catalytic triad of trypsin, chymotrypsin, thrombin, and other serine proteases
  • One-carbon donor via serine hydroxymethyltransferase to the folate cycle for nucleotide biosynthesis
  • Component of natural moisturizing factor in stratum corneum skincare formulations
  • Standard amino acid in defined cell-culture media (DMEM, RPMI) at 0.4 mM concentration
  • Pharmaceutical excipient and parenteral nutrition amino-acid component

Safety Information

Generally Recognized As Safe (GRAS) by FDA for dietary use, with no upper intake limit established. GHS: not classified as hazardous. No OSHA PEL. Acute oral toxicity is essentially nil — rat LD50 exceeds 5 g/kg. Standard handling with nitrile gloves and dust mask if weighing large quantities is sufficient. The only practical caveat is that L-serine supplementation at gram-per-day doses is being studied for ALS and may interact with the methionine cycle, so research-grade L-serine should not be self-administered outside a clinical trial.

This safety summary is for educational reference only and may not be complete. It is not a substitute for Safety Data Sheets (SDS), medical advice, or professional chemical safety guidance. Always consult appropriate SDS and qualified professionals before handling chemicals.

Constituent Elements

Frequently Asked Questions

What is the molar mass of serine?
L-serine (C3H7NO3) has a molar mass of 105.093 g/mol, calculated from 3 carbons (3 x 12.011 = 36.033) + 7 hydrogens (7 x 1.008 = 7.056) + 1 nitrogen (14.007) + 3 oxygens (3 x 15.999 = 47.997). The L enantiomer is the proteinogenic form; D-serine is also biologically active in mammals as a co-agonist at the NMDA receptor in the brain.
Why is serine phosphorylation so important?
Phosphate addition by Ser/Thr kinases changes the local charge by two negative units and adds a hydrogen-bond acceptor, which can dock 14-3-3 proteins, BRCT domains, FHA domains, and other phosphobinding modules to drive protein-protein interactions. The reversibility — kinases on, phosphatases off, both regulated independently — gives cells a fast switching network for cell-cycle checkpoints, glycogen metabolism, MAPK cascades, and gene transcription. Roughly 80 percent of identified phosphosites in the human proteome are serine.
What are serine proteases?
Serine proteases are enzymes that cleave peptide bonds using an active-site serine as the nucleophile, with histidine acting as a base to deprotonate the serine hydroxyl and aspartate stabilizing the protonated histidine — the classic Ser-His-Asp catalytic triad. The family includes the digestive enzymes trypsin and chymotrypsin, the entire coagulation cascade (thrombin, factor Xa, factor VIIa), the complement cascade, and tissue plasminogen activator. They're targets for blood thinners like dabigatran (thrombin) and rivaroxaban (factor Xa).