DL-Serine

Description

DL-Serine is a kind of neutral aliphatic amino acids containing hydroxyl groups with polarity but being uncharged, and belongs to nonessential amino acids for human body. It has a high content in sericin silk protein and fibroin protein. It can be formed from the methyl transfer reaction of glycine. It can also be converted to pyruvate or hydroxy pyruvate through deamination. It is also an important raw material for in vivo synthesis of choline and cysteine.

Chemical properties

DL-Serine is a kind of colorless monoclinic columnar or lamellae crystal. It is soluble in water (at 20℃, the water solubility is 380g/L), insoluble in ether and ethanol; Decomposition point: 246℃.

The Uses of DL-Serine

DL-Serine is used in the synthesis of novel tryptoline derivatives as IDO (indoleamine 2,3-Deoxygenase) inhibitors, for potential use in Alzheimer’s treatment.

Definition

ChEBI: Serine is an alpha-amino acid that is alanine substituted at position 3 by a hydroxy group. It has a role as a fundamental metabolite. It is an alpha-amino acid and a polar amino acid. It contains a hydroxymethyl group. It is a conjugate base of a serinium. It is a conjugate acid of a serinate. It is a tautomer of a serine zwitterion.

What are the applications of Application

Serine is a non-essential amino acid and a natural ligand and allosteric activator of pyruvate kinase M2. Serine helps retain the skin's moisture balance.

Preparation

DL-serine is obtained by complexing glycine under the catalysis of copper ions and then combining with formaldehyde under alkaline conditions, followed by acidification, ion exchange, and crystallization in ethanol.?

Synthesis Reference(s)

Canadian Journal of Chemistry, 33, p. 1119, 1955 DOI: 10.1139/v55-131
The Journal of Organic Chemistry, 35, p. 1505, 1970 DOI: 10.1021/jo00830a054

Biochem/physiol Actions

NMDA agonist acting at the glycine site; precursor of glycine by serine hydroxymethyltransferase

Safety Profile

When heated to decomposition emits toxic fumes of NOx.

in vitro

DL-Serine, a fundamental metabolite, is a mixture of D-Serine and L-Serine. DL-Serine has antiviral activity against the multiplication of tobacco mosaic virus (TMV).
Subcutaneous injection of DL-serine increases the number and size of renal tubular cell tumors in male W rats treated with 500 or 1,000 ppm N-ethyl-N-hydroxyethylnitrosamine.