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D-Cycloserine, 98+%

Codice prodotto. 11499126
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Codice prodotto. 11499126 Fornitore Thermo Scientific Alfa Aesar N. del fornitore A18000.03
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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

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
TRUSTED_SUSTAINABILITY

Identificatori chimici

CAS 68-41-7
Formula molecolare C3H6N2O2
Molecular Weight (g/mol) 102.093
Numero MDL MFCD00005353
InChI Key DYDCUQKUCUHJBH-UWTATZPHSA-N
Sinonimo 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

Specifica

Materiale o nome chimico D-Cycloserine
Punto di fusione 137°C (decomposition)
Beilstein 80798
Indice di Merck 14,2751
Informazioni di solubilità Soluble in water; Slightly soluble in methanol and propylene glycol; Insoluble in chloroform and ether.
Quantità 1 g
Peso formulazione 102.09
Optical Rotation +115° (c=2 in Water)
Percent Purity ≥98%

RUO – Research Use Only

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