D-cycloserine

D-cycloserine

(4R)-4-amino-1,2-oxazolidin-3-one

PubChem CID: 6234

D-cycloserine is a 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanineD-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis). It has a role as a metabolite, an antitubercular agent, an antimetabolite, an antiinfective agent and a NMDA receptor agonist. It is a 4-amino-1,2-oxazolidin-3-one, an organonitrogen heterocyclic antibiotic and an organooxygen heterocyclic antibiotic. It is a conjugate base of a D-cycloserine(1+). It is an enantiomer of a L-cycloserine. It is a tautomer of a D-cycloserine zwitterion.

2D Structure

Properties

SMILES

Synonyms(20)