D-Serine
[CAS# 312-84-5]

Identification

• Classification: Biochemical >> Common amino acids and protein drugs
• Name: D-Serine
• Synonyms: D-2-Amino-3-hydroxypropanoic acid
• Molecular Formula: C₃H₇NO₃
• Molecular Weight: 105.09
• Protein Sequence: S
• CAS Registry Number: 312-84-5
• EC Number: 206-229-4
• SMILES: C([C@H](C(=O)O)N)O

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Melting point: 218 - 220 °C (Decomposes) (Expl.)
• Boiling point: 394.8±32.0 °C 760 mmHg (Calc.)^*
• Flash point: 192.6±25.1 °C (Calc.)^*
• Solubility: H2O: 0.1 g/mL (Expl.)
• Index of refraction: 1.519 (Calc.)^*
• Alpha: -14.75 ° (c=10 2 n hcl) (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

D-Serine is the D-enantiomer of the amino acid serine, with the molecular formula C₃H₇NO₃. It is characterized by the presence of a hydroxymethyl side chain attached to the α-carbon, which is chiral, and in this case, exhibits the D-configuration, opposite to the more common L-configuration found in proteins.

D-Serine occurs naturally in the mammalian central nervous system and functions as an important neuromodulator. It acts as a co-agonist at the glycine binding site of the N-methyl-D-aspartate (NMDA) receptor, which is involved in synaptic plasticity, learning, and memory. Its interaction with NMDA receptors modulates excitatory neurotransmission and plays a role in neurodevelopmental and neurodegenerative processes.

Biosynthetically, D-serine is produced in the brain by the enzyme serine racemase, which converts L-serine into D-serine. It is also metabolized by D-amino acid oxidase, which regulates its levels. Imbalances in D-serine concentrations have been linked to various neurological disorders, including schizophrenia, Alzheimer’s disease, and amyotrophic lateral sclerosis.

Chemically, D-serine is a zwitterion at physiological pH, with a protonated amino group and a deprotonated carboxyl group. It is soluble in water and polar solvents due to its polar functional groups. The molecule is stable under physiological conditions but can undergo typical amino acid reactions such as peptide bond formation.

In research and therapeutic contexts, D-serine is studied for its potential to modulate NMDA receptor function and as a candidate for treatment of cognitive impairments and psychiatric conditions. Its role as a signaling molecule highlights the importance of D-amino acids in human physiology beyond their classical metabolic functions.

In summary, D-serine is the D-enantiomer of serine, acting as a neuromodulator in the central nervous system by co-activating NMDA receptors. Its biological and chemical properties make it significant in neuroscience research and potential therapeutic applications.

References

2013. Amino acid analysis: current topics and trends. Analytical and Bioanalytical Chemistry.
DOI: 10.1007/s00216-013-7255-9

1994. The Glycine Site on the NMDA Receptor: Structure-Activity Relationships and Therapeutic Potential. Journal of Medicinal Chemistry.
DOI: 10.1021/jm00050a001

2005. The dsdA gene from Escherichia coli provides a novel selectable marker for plant transformation. Plant Molecular Biology.
DOI: 10.1007/s11103-004-7902-9