DL-O-Phosphoserine
DL-O-Phosphoserine Basic information
- Product Name:
- DL-O-Phosphoserine
- Synonyms:
-
- DL-2-Amino-3-hydroxypropanoic acid 3-phosphate, DL-Serine monophosphoric acid, DL-SOP
- Serophen
- DL-O-Phosphorylserine
- DL-O-Serine phosphate
- Energoserina
- NSC 90791
- Serine, dihydrogen phosphate (ester) (9CI)
- Serine, dihydrogen phosphate (ester), DL- (8CI)
- CAS:
- 17885-08-4
- MF:
- C3H8NO6P
- MW:
- 185.07
- EINECS:
- 241-834-7
- Product Categories:
-
- Amino Acids
- Biochemistry
- Biological-modified Amino Acids
- Mol File:
- 17885-08-4.mol
DL-O-Phosphoserine Chemical Properties
- Melting point:
- 190 °C(lit.)
- Boiling point:
- 475.4±55.0 °C(Predicted)
- Density
- 1.809
- storage temp.
- -15°C
- solubility
- H2O: 50 mg/mL hot, clear, colorless to slightly yellow
- form
- Solid
- pka
- 1.71±0.10(Predicted)
- color
- White to Off-White
- Merck
- 7363
- BRN
- 1726828
- InChI
- InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1
- InChIKey
- BZQFBWGGLXLEPQ-REOHCLBHSA-N
- SMILES
- C(O)(=O)[C@H](COP(O)(O)=O)N
- CAS DataBase Reference
- 17885-08-4(CAS DataBase Reference)
MSDS
- Language:English Provider:SigmaAldrich
DL-O-Phosphoserine Usage And Synthesis
Chemical Properties
White to faint beige crystalline powder
Uses
DL-O-Phosphoserine is used in alternative pathways for biosynthesis of cysteine and of selenocysteine.
Definition
ChEBI: A serine derivative that is serine substituted at the oxygen atom by a phosphono group.
Biochem/physiol Actions
O-Phospho-DL-serine (pSer) is used in the study of non-enzymatic aminophospholipid glycation.
in vivo
O-phospho-L-serin can be used in retinal research to explore the regulatory mechanism of Müller glial cell proliferation and photoreceptor regeneration; in bone repair research, to evaluate the effects on bone cement performance and bone healing; in insect research, to identify the role of D-serine in insect growth and development. In the zebrafish light-damaged retinal model experiment, O-phospho-L-serin (20 mM, 0.5 μL; iv; injected before light treatment; single dose) can significantly reduce the number of proliferating cell nuclear antigen (PCNA)-positive Müller glial cells 51 hours after light damage, and inhibit the regeneration of cones in the light-damaged retina, but has no significant effect on the number of light-induced photoreceptor cell death[1].
In a miniature pig mandibular bone defect model experiment, a modified bone cement prepared by surgical implantation of a mixture of O-phospho-L-serin (Biozement D (2 g)-collagen-I (2.5%)-phosphoserine (50 mg)) was administered. Compared with the unmodified bone cement, the treated group had a higher absorption rate and bone regeneration rate, which effectively promoted bone healing[2].
In a silkworm growth and development experiment, O-phospho-L-serin (20 mM, 1 mL; added to feed; daily administration, from first to fifth instar larvae) delayed the development of silkworm larvae by about 6 days, significantly reduced the survival rate of larvae, and reduced the D-serine level in larvae until the cocooning stage compared with the control group[3].
| Animal Model: | Zebrafish retinal light damage model[1] |
| Dosage: | 0.65% saline containing either 20 mM O-phospho-L-serine (L-SOP), 0.5 μL |
| Administration: | Intravitreally injection via Hamilton syringe; single dose |
| Result: | Decreased the number of PCNA-positive Müller glia 51 hours after light damage. Inhibited the regeneration of cone photoreceptors in the light-damaged retina. There was no significant difference in the number of light-induced photoreceptor cell deaths between the O-phospho-L-serin-injected group and the control group 24 hours after light treatment. |
IC 50
Human Endogenous Metabolite
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DL-O-Phosphoserine(17885-08-4)Related Product Information
- Fmoc-O-(benzylphospho)-L-serine
- Phosphatidylserine
- FMOC-SER(PO3H2)-OH
- Fmoc-O-(benzylphospho)-L-threonine
- O-Phospho-L-serine
- DL-O-Phosphoserine
- DL-Serine
- DOPS
- BOC-O-DIPHENYLPHOSPHO-L-SERINE
- O-PHOSPHO-D-SERINE
- DL-O-PHOSPHOSERINE, BARIUM SALT
- 1-PALMITOYL-SN-GLYCERO-3-PHOSPHO-L-SERINE SODIUM SALT
- 1,2-DILAUROYL-SN-GLYCERO-3-PHOSPHO-L-SERINE SODIUM SALT
- O-PHOSPHO-L-THREONINE
- 1-STEAROYL-2-OLEOYL-SN-GLYCERO-3-[PHOSPHO-L-SERINE](SODIUM SALT)
- 1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHO-L-SERINE, SODIUM SALT
- BOC-O-DIBENZYLPHOSPHO-L-SERINE
- N(ALPHA)-BOC-O-(DIMETHYLPHOSPHO)-L-THREO