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S4250

Sigma-Aldrich

D-Serine

≥98% (TLC)

Synonym(s):
(R)-2-Amino-3-hydroxypropionic acid, β-Hydroxyalanine, Ser
Empirical Formula (Hill Notation):
C3H7NO3
CAS Number:
Molecular Weight:
105.09
Beilstein:
1721403
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥98% (TLC)

form

powder

technique(s)

ligand binding assay: suitable

color

white to off-white

application(s)

cell analysis

SMILES string

N[C@H](CO)C(O)=O

InChI

1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1

InChI key

MTCFGRXMJLQNBG-UWTATZPHSA-N

Gene Information

human ... GRIN1(2902)

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General description

D-serine is an unusual amino acid expressed in the mammalian brain.
D-serine is a dextro amino acid present in neurons, astrocytes, and microglia. It is synthesized from L-serine by the enzyme serine racemase. Racemase also catalyzes the breakdown of D-serine into ammonia and pyruvate. It is oxidized to hydroxypyruvate by D-amino acid oxidase.

Application

D-serine has been used as a substrate in D-amino acid oxidase (DAO) activity in human 1321N1 astrocytoma cells. It has also been used in intracerebroventricular administration in rat for the induction of antinociceptive effect.
D-serine has been used to prevent glycine-dependent desensitization of N-methyl D-aspartate receptor (NMDAR) and to study its effects on NMDARs to correct behavioral abnormalities in rats after partial sciatic nerve ligation (PSNL).

Packaging

5, 25 g in poly bottle

Biochem/physiol Actions

D-serine is an agonist and glycine mimic which is active at the strychnine-insensitive glycine binding site associated with the N-methyl-D-aspartate (NMDA) receptor as well as the inhibitory post-synaptic glycine receptor. Along with glutamate, it has a role in various physiological processes including synaptic plasticity and receptor transmission. Dysregulation of D-serine signaling has been linked with neurodegenerative diseases and disorders.
D-serine is essential for the normal development of dendrites, neuroblast migration and may have therapeutic potential for treating schizophrenia and depression states. The levels of D-serine is elevated in traumatic brain injury (TBI).

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. S4250.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

  1. How does the storage temperature relate to shipping conditions?

    The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment. See Shipping and Storage for more information.

  2. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  3. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  4. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  5. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  6. What is the melting point for S4250, D-Serine?

    The melting point for this product is 228°C.

  7. What is the solubility of Product S4250, D-Serine?

    This product is soluble in water at a concentration of 50mg/mL. It is also soluble in 1M hydrochloric acid.  It is not soluble in ethanol or ether.

  8. Is Product S4250, D-Serine, suitable for human consumption?

    This product is not suitable for human consumption.  This product is intended primarily for laboratory research purposes and should not be used for any other purposes, including but not limited to, in vitro diagnostic purposes, in foods, drugs, medical devices, or cosmetics for humans or animals, or for other commercial purposes.

  9. Can D-Serine, Product No. S4250, be autoclaved?  

    Yes, solutions of this product can be autoclaved.

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Differential roles of hippocampal glutamatergic receptors in neuropathic anxiety-like behavior after partial sciatic nerve ligation in rats.
Wang XQ
BMC Neuroscience, 16, 14-14 (2015)
Enhanced astrocytic d-serine underlies synaptic damage after traumatic brain injury
Perez EJ, et al.
The Journal of Clinical Investigation, 127(8), 3114-3125 (2017)
D-amino acids in the brain: D-serine in neurotransmission and neurodegeneration.
Wolosker H
FEBS Journal, 275(14), 3514-3526 (2008)
Imaging calcium concentration dynamics in small neuronal compartments.
Yasuda R
Science's STKE : Signal Transduction Knowledge Environment, 219, p15-p15 (2004)
High dose D-serine in the treatment of schizophrenia.
Kantrowitz JT
Schizophrenia Research, 121(1-3), 125-130 (2010)

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