D-Cycloserine, 98+%, Thermo Scientific Chemicals

Description

D-cycloserine, CAS # 68-41-7, is an amino acid analog of the amino acid D-alanine with broad-spectrum antibiotic activity.

Cycloserine is an amino acid analog antibiotic used for the treatment of tuberculosis and rarely used for the treatment of noninfectious diseases. It acts as a competitive inhibitor of D-alanine during peptidoglycan synthesis. It inhibits bacterial cell wall biosynthesis and prevents the conversion of D-Alanine to L-Alanine.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

General Description

• D-cycloserine is an analog of the amino acid D-alanine produced by Streptomyces garyphalus or S. orchidaceus and shows antibacterial activity
• The activity of this compound is related to the ability to interfere with bacterial cell wall synthesis by competitively inhibiting two enzymes, L-alanine racemase (responsible for the formation of D-alanine from L-alanine) and D-alanine ligase (the enzyme responsible for the incorporation of D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis). This interaction impairs the peptidoglycan formation, which is needed for bacterial cell wall synthesis

Application

• Depending on the concentration and the organism’s susceptibility, this compound may present bactericidal or bacteriostatic activities
• Despite its antibiotic activity, this compound also has an excitatory activity
• It has been described that D-cycloserine can bind to the glycine binding site of the NMDA receptor in the central nervous system
• This compound presents an inhibitory activity against GABA transaminase

Specifications

Chemical Identifiers

• CAS: 68-41-7
• Molecular Formula: C3H6N2O2
• Molecular Weight (g/mol): 102.093
• MDL Number: MFCD00005353
• InChI Key: DYDCUQKUCUHJBH-UWTATZPHSA-N
• Synonym: d-cycloserine, cycloserine, seromycin, orientomycin, oxamycin, cyclorin, cyclo-d-serine, cicloserina, farmiserina, miroseryn
• PubChem CID: 6234
• ChEBI: CHEBI:40009
• IUPAC Name: (4R)-4-amino-1,2-oxazolidin-3-one
• SMILES: C1C(C(=O)NO1)N

• Melting Point: 137°C (decomposition)
• Beilstein: 80798
• Merck Index: 14,2751
• Solubility Information: Soluble in water; Slightly soluble in methanol and propylene glycol; Insoluble in chloroform and ether.
• Formula Weight: 102.09
• Percent Purity: ≥98%
• Quantity: 5 g
• Optical Rotation: +115° (c=2 in Water)
• Chemical Name or Material: D-Cycloserine

Safety and Handling

EINECSNumber	200-688-4
RTECSNumber	NY2975000
TSCA	No
Recommended Storage	Keep cold

SDS

RUO – Research Use Only