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D-Cycloserine

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D-Cycloserine Basic information
A second-line anti-TB drug Chemical properties Application Production process
Product Name:D-Cycloserine
Synonyms:CYCLOSERINE;D-CYCLOSERINE;D-CYCLOSERINE, STREPTOMYCES ORCHIDACEUS;D-4-AMINO-3-ISOXAZOLIDINONE;(R)-(+)-CYCLOSERINE;(R)-4-AMINO-ISOXAZOLIDIN-3-ONE;(R)-4-AMINO-3-ISOXAZOLIDINONE;R(+)-4-AMINO-3-ISOXAZOLIDINONE
CAS:68-41-7
MF:C3H6N2O2
MW:102.09
EINECS:200-688-4
Product Categories:VARIOUSAMINE;Miscellaneous Biochemicals;chiral;Amines (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry;Amino Acids;Glutamate receptor;Glutamate;Antibiotics;API;SEROMYCIN;amino;Inhibitors;Amino acid
Mol File:68-41-7.mol
D-Cycloserine Structure
D-Cycloserine Chemical Properties
mp 147 °C (dec.)(lit.)
alpha 111 º (C=5, 2N NaOH)
storage temp. −20°C
form powder
Water Solubility SOLUBLE
Sensitive Air Sensitive
Merck 14,2751
BRN 80798
CAS DataBase Reference68-41-7(CAS DataBase Reference)
NIST Chemistry ReferenceCycloserine(68-41-7)
Safety Information
Hazard Codes Xn
Risk Statements 5-20
Safety Statements 38-36/37-24/25
WGK Germany 2
RTECS NY2975000
10-23
Hazardous Substances Data68-41-7(Hazardous Substances Data)
MSDS Information
ProviderLanguage
D-Cycloserine English
ACROS English
SigmaAldrich English
ALFA English
D-Cycloserine Usage And Synthesis
A second-line anti-TB drugD-cycloserine is a broad-spectrum polypeptide antibiotic produced by Streptomyces lavendulae and Streptomyces orchidaceus or synthesized by chemical methods. As white crystals with strong hygroscopic nature, it is soluble in water, slightly soluble in lower alcohols, acetone and dioxane, and hardly soluble in chloroform and petroleum ether. It is relatively stable in alkaline solution and decomposes rapidly in acidic or neutral solutions. As a broad-spectrum antibiotic, cycloserine is inhibitive against most Gram-positive and Gram-negative bacteria, rickettsia and some protozoa, with the exception of Mycobacterium tuberculosis., It is also effective on some of the Mycobacterium tuberculosis strains with tolerance to streptomycin, vinactane para-aminosalicylic acid, isoniazid and pyrazinamide. Cycloserine slightly synergizes with isoniazid in the inhibition of Mycobacterium tuberculosis H37RV, but it neither synergizes nor antagonizes against streptomycin. The product is a bacteriostatic agent, and thus won’t exert bactericidal effect even when increasing the dose or prolonging the action time with bacteria.
The Mechanism of D-cycloserine’s antibacterial action is to inhibit the biosynthesis of peptidoglycan of the cell wall. As it is a structural analog of D-alanine, D-cycloserine can competitively inhibit the activities of alanine racemase and D-alanyl-D-alanine synthetase, which are two important enzymes in peptidoglycan synthesis. D-cycloserine shows weak inhibitive activity against Mycobacterium tuberculosis which is only 1/10 to 1/20 that of streptomycin. The advantage of the product is that it is effective on drug-resistant Mycobacterium tuberculosis strains and less likely to induce drug resistance. The product can be used with other anti-tuberculosis drugs in the treatment of tuberculosis caused by drug-resistant Mycobacterium tuberculosis.
Cycloserine is a second-line anti-tuberculosis drug. It can inhibit the growth of Mycobacterium tuberculosis, but the effect is relatively weaker than that of the first-line drugs. Its efficacy in tuberculosis treatment is relatively low. Use the drug alone may produce drug resistance, but the resistance occurs slowly compared with that of other anti-tuberculosis drugs. No cross-resistance has been found between cycloserine and other anti-tuberculosis drugs. The mechanism of its antibacterial action is to inhibit the synthesis of peptidoglycan of bacterial cell wall, causing defective in cell wall architecture. The main structural component of the bacterial cell wall is peptidoglycan, which is composed of N-acetylglucosamine (GNAc) and N-acetylmuramic acid (MNAc). N-acetylmuramic acid is linked with pentapeptide and connects N-acetylglucosamine in a reduplicated and alternative manner. The formation of cytoplasmic peptidoglycan precursor may be hampered by cycloserine, as the latter can hinder the racemase and the synthetase of D-alanine, and thus blocks the formation of N-acetylmuramic acid.
The above information is edited by the Chemicalbook of Liu Huimin.
Chemical propertiesColorless needle or leafy crystals, or amorphous powder; melting point 155-156℃ (decomposition). Soluble in water; slightly soluble in methanol, ethanol, butanol, propylene glycol, isopropyl alcohol and acetone; and hardly soluble or insoluble in toluene, chloroform, ether, pyridine, benzene and carbon disulfide.
Application1. Used as an antibiotic medicine in the treatment of drug-resistant Mycobacterium tuberculosis infection.
2. Biochemical research
Production processD-Cycloserine can be obtained through fermentation technique or through direct synthesis. The bacteria used in the fermentation is Actinomyces laven-dulae. The fermentation medium consists of dextrin, dextrose, starch, soybean powder, yeast powder, ammonium sulfate, ammonium nitrate, calcium carbonate, sodium chloride, magnesium sulfate and soybean oil. In the synthesis process, D-cycloserine is obtained from β-aminooxy alanine ethyl ester hydrochloride by reaction with potassium hydroxide in a cyclization reaction.
Chemical PropertiesWhite to pale yellow cryst. powder
Usageantibacterial (tuberculostatic)
UsageD-Cycloserine inhibits cell wall biosynthesis (D-Ala peptide bond formation). D-Cycloserine also prevents conversion of D-Ala to L-Ala. D-Cycloserine is an bacteriostatic. D-Cycloserine is an antibiot ic against Gram-negative bacteria.
D-Cycloserine Preparation Products And Raw materials
Raw materialsCalcium carbonate-->Ammonium nitrate-->SOYBEAN OIL-->Dextrin-->streptomyces avermifilis-->D-Alanine
Tag:D-Cycloserine(68-41-7) Related Product Information
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