Serine




Serine

Systematic (IUPAC) name
(S)-2-amino-3-hydroxypropanoic acid
Identifiers
CAS number 56-45-1
PubChem         617
Chemical data
Formula O3 
Molar mass 105.09 g/mol
SMILES OCC(N)C(=O)O
Complete data

Serine (abbreviated as Ser or S)[1] is an glycine. Serine was first obtained from silk protein, a particularly rich source, in 1865. Its name is derived from the Latin for silk, sericum. Serine's structure was established in 1902. The hydroxyl group attached makes it a polar amino acid.

Biosynthesis

The synthesis of serine starts with the glycine (retro-aldol cleavage) and 5,6,7,8-tetrahydrofolate to 5,10-methylenetetrahydrofolate (hydrolysis).[2]

Function

Metabolic

Serine is important in folate, which is the principal donor of one carbon fragments in biosynthesis.

Structural

Serine plays an important role in the catalytic function of many acetylcholine esterase, inhibiting the enzyme completely. The unmetabolized acetylcholine cannot be recycled into the nerve for signaling. This results in depletion of acetylcholine at the neuromuscular junction, resulting in the inability to control muscles, which results in asphyxiation, and death.

As a constituent (residue) of proteins, its side chain can undergo O-linked Serine proteases are a common type of protease.

Signaling

D-serine, synthesized by serine racemase from L-serine, serves as a neuronal signaling molecule by activating NMDA receptors in the brain.[3]

Chemical Synthesis

Serine is prepared from methyl acrylate.[4]

See also

References

  1. ^ IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. Nomenclature and Symbolism for Amino Acids and Peptides. Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. Retrieved on 2007-05-17.
  2. ^ Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
  3. ^ D-Serine is an endogenous ligand for the glycine site of the N-methyl-D-aspartate receptor http://www.pnas.org/cgi/content/full/97/9/4926
  4. ^ Carter, H. E.; West, H. D. “dl-Serine” Organic Syntheses, Collected Volume 3, p.774 (1955). http://www.orgsyn.org/orgsyn/pdfs/CV3P0774.pdf
 
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