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C3909

Sigma-Aldrich

D-Cycloserine

synthetic

Synonym(s):

(R)-4-Amino-3-isoxazolidone, 4-Amino-3-isoxazolidinone

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About This Item

Empirical Formula (Hill Notation):
C3H6N2O2
CAS Number:
68-41-7
Molecular Weight:
102.09
Beilstein/REAXYS Number:
80798
EC Number:
200-688-4
MDL number:
MFCD00005353
UNSPSC Code:
12352209
PubChem Substance ID:
24277962
NACRES:
NA.28
Pricing and availability is not currently available.

biological source

synthetic

form

powder

mp

147 °C (dec.) (lit.)

solubility

water: 50 mg/mL, clear, colorless to light yellow

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycobacteria

mode of action

cell wall synthesis | interferes

storage temp.

−20°C

SMILES string

N[C@@H]1CONC1=O

InChI

1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1

InChI key

DYDCUQKUCUHJBH-UWTATZPHSA-N

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Show Differences

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Fmoc-Ala-Thr(psiMe,Mepro)-OH Novabiochem®

8.52180

Fmoc-Ala-Thr(psiMe,Mepro)-OH

Fmoc-Val-Thr(psiMe,Mepro)-OH Novabiochem®

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Fmoc-Val-Thr(psiMe,Mepro)-OH

Fmoc-Ala-Ser(psiMe,Mepro)-OH Novabiochem®

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Fmoc-Ala-Ser(psiMe,Mepro)-OH

Fmoc-Tyr(tBu)-Thr(psiMe,Mepro)-OH Novabiochem®

8.52182

Fmoc-Tyr(tBu)-Thr(psiMe,Mepro)-OH

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

functional group

hydroxyl

functional group

hydroxyl

functional group

hydroxyl

functional group

hydroxyl

product line

Novabiochem®

product line

Novabiochem®

product line

Novabiochem®

product line

Novabiochem®

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

application(s)

peptide synthesis

application(s)

peptide synthesis

application(s)

peptide synthesis

application(s)

peptide synthesis

form

powder

form

powder

form

powder

form

powder

General description

Chemical structure: amino acid derivatives

Application

D-cycloserine has been used to inhibit serine hydroxymethyltransferase.[1]

Biochem/physiol Actions

Mode of Action: Inhibits cell wall biosynthesis (D-Ala peptide bond formation). Also prevents conversion of D-Ala to L-Ala. Bacteriostatic.
Partial agonist at the glycine modulatory site of NMDA glutamatergic receptors; antibiotic against Gram-negative bacteria.
Mode of Resistance: D-Ala transport interference.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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    Certificates of Analysis (COA)

    Lot/Batch Number
    087H5023
    070K0852
    056F5830
    039H5005
    119H0952

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    L-serine treatment may improve neurorestoration of rats after permanent focal cerebral ischemia potentially through improvement of neurorepair
    Sun L, et al.
    PLoS ONE, 9(3), e93405-e93405 (2014)
    Michael Davis et al.
    Biological psychiatry, 60(4), 369-375 (2006-08-22)
    Administration of benzodiazepines or serotonin reuptake inhibitors in combination with behavior therapy for the treatment of many anxiety disorders has generally lead to only modest gains. In this article we suggest that pharmacotherapy aimed not at treating the symptoms of
    Marta Portero-Tresserra et al.
    Neurobiology of learning and memory, 100, 1-11 (2012-12-04)
    It is well established that D-cycloserine (DCS), a partial agonist of the NMDA receptor glycine site, enhances learning and memory processes. Although the effects of DCS have been especially elucidated in the extinction and reconsolidation of aversive behavioral paradigms or
    Ram Maharjan et al.
    Molecular biology and evolution, 32(2), 380-391 (2014-11-13)
    Evolutionary innovations are dependent on mutations. Mutation rates are increased by adverse conditions in the laboratory, but there is no evidence that stressful environments that do not directly impact on DNA leave a mutational imprint on extant genomes. Mutational spectra
    Karyn M Myers et al.
    Biological psychiatry, 71(11), 947-955 (2012-05-15)
    D-cycloserine (DCS) is an N-methyl-D-aspartate (NMDA) receptor partial agonist that facilitates extinction of conditioned fear in animals and cue exposure therapy (CET) for fear and anxiety disorders in people. Recent preclinical and clinical studies have examined the effect of DCS
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