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C1159

Sigma-Aldrich

L-Cycloserine

Synonym(s):

(S)-4-Amino-3-isoxazolidone

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About This Item

Empirical Formula (Hill Notation):
C3H6N2O2
CAS Number:
339-72-0
Molecular Weight:
102.09
Beilstein/REAXYS Number:
80799
EC Number:
206-427-0
MDL number:
MFCD00064324
UNSPSC Code:
12352202
eCl@ss:
32160406
PubChem Substance ID:
24278296
NACRES:
NA.77

assay

≥95% (TLC)

Quality Level

200

form

powder

mp

146 °C

solubility

H2O: 50 mg/mg protein

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-/m0/s1

InChI key

DYDCUQKUCUHJBH-REOHCLBHSA-N

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Biochem/physiol Actions

Blocks sphingosine biosynthesis by inhibition of ketosphinganine synthetase. Cytotoxicity toward neuroblastoma and medulloblastoma cells mediated by suppression of ganglioside synthesis.
L-cycloserine is a potent inhibitor of serine palmitoyltransferase, the first step of sphingolipid synthesis.

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)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Elisa Caiola et al.
Cells, 9(8) (2020-07-29)
Non-small-cell lung cancer (NSCLC) cell lines vary in their sensitivity to glutaminase inhibitors, so it is important to identify the metabolic assets underling their efficacy in cancer cells. Even though specific genetic lesions such as in KRAS and LKB1 have
J Cinatl et al.
Anticancer research, 19(6B), 5349-5354 (2000-03-04)
Human neuroblastoma and medulloblastoma express abnormal ganglioside patterns especially GD2 and GM2 which are important for tumour growth. We tested the effects of L-cycloserine (L-CS), a potent inhibitor of synthesis of glycosphingolipids, on the growth, viability and expression of GD2
David M Pereira et al.
Marine drugs, 12(1), 54-68 (2013-12-26)
We describe the effect of a chemically characterized lipophilic extract obtained from Marthasterias glacialis L. against human breast cancer (MCF-7) and human neuroblastoma (SH-SY5Y) cell lines. Evaluation of DNA synthesis revealed that both cell lines were markedly affected in a
Peirong Hu et al.
Journal of neuroscience research, 94(11), 1152-1168 (2016-09-18)
Currently, presymtomatic hematopoietic stem and progenitor cell transplantation (HSPCT) is the only therapeutic modality that alleviates Krabbe's disease (KD)-induced central nervous system damage. However, all HSPCT-treated patients exhibit severe deterioration in peripheral nervous system function characterized by major motor and
Domenico Sergi et al.
Nutritional neuroscience, 23(4), 321-334 (2018-07-24)
A high-fat diet induces hypothalamic inflammation in rodents which, in turn, contributes to the development of obesity by eliciting both insulin and leptin resistance. However, the mechanism by which long-chain saturated fatty acids trigger inflammation is still contentious. To elucidate
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