① L-CYCLOSERINE is produced by fermentation, extraction, and refining of actinomycetes. ② L-CYCLOSERINE can be prepared by reacting serine methyl ester hydrochloride with chloroform under the catalysis of phosphorus pentachloride to remove the hydroxyl group, followed by reaction with hydroxylamine in sodium hydroxide solution.
antibacterial, coccidiostat
L-Cycloserine is an irreversible inhibitor of 3-ketodihydrosphingosine synthetase.
ChEBI: A 4-amino-1,2-oxazolidin-3-one that has S configuration. An antibiotic isolated from Erwinia uredovora.
L-cycloserine is a potent inhibitor of serine palmitoyltransferase, the first step of sphingolipid synthesis.
Purify cycloserine by recrystallisation from aqueous EtOH or MeOH or aqueous NH3/EtOH or isoPrOH. Also recrystallise it from aqueous ammoniacal solution at pH 10.5 (100mg/mL) by diluting with 5 volumes of isopropanol and then adjusting to pH 6 with acetic acid. An aqueous solution, buffered to pH 10 with Na2CO3, can be stored in a refrigerator for 1week without decomposition. UV: max at 226nm (A1cm 1% 4.02). The tartrate salt has m 165-166o (dec), 166-168o (dec), and [] D 24 -41o (c 0.7, H2O). [Stammer et al. J Am Chem Soc 79 3236 1959, UV: Kuehl J Am Chem Soc 77 2344 1955, Beilstein 27 III/IV 5549.]
