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D-Cycloserine, 98+%

D-cycloserine, CAS # 68-41-7, is an amino acid analog of the amino acid D-alanine with broad-spectrum antibiotic activity. | CAS: 68-41-7 | C3H6N2O2 | 102.093 g/mol

$141.05 - $519.00

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
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AAA1800003
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Thermo Scientific Chemicals
A1800003
1 g
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AAA1800006
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Thermo Scientific Chemicals
A1800006
5 g
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Description

Description

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

68-41-7
102.093
DYDCUQKUCUHJBH-UWTATZPHSA-N
6234
(4R)-4-amino-1,2-oxazolidin-3-one
C3H6N2O2
MFCD00005353
d-cycloserine, cycloserine, seromycin, orientomycin, oxamycin, cyclorin, cyclo-d-serine, cicloserina, farmiserina, miroseryn
CHEBI:40009
C1C(C(=O)NO1)N

Specifications

137°C (decomposition)
C3H6N2O2
80798
d-cycloserine, cycloserine, seromycin, orientomycin, oxamycin, cyclorin, cyclo-d-serine, cicloserina, farmiserina, miroseryn
DYDCUQKUCUHJBH-UWTATZPHSA-N
(4R)-4-amino-1,2-oxazolidin-3-one
102.093
CHEBI:40009
102.09
D-Cycloserine
68-41-7
MFCD00005353
14,2751
Soluble in water; Slightly soluble in methanol and propylene glycol; Insoluble in chloroform and ether.
C1C(C(=O)NO1)N
1 g
6234
+115° (c=2 in Water)
≥98%
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Safety and Handling

Safety and Handling

EINECSNumber : 200-688-4

RTECSNumber : NY2975000

TSCA : No

Recommended Storage : Keep cold

SDS
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RUO – Research Use Only