(2R)-2-ammonio-3-hydroxypropanoate

Base Information

• Chemical Name: (2R)-2-ammonio-3-hydroxypropanoate
• CAS No.: 312-84-5
• Molecular Formula: C3H7NO3
• Molecular Weight: 215.129
• Hs Code.: 2922.49
• Mol file: 312-84-5.mol

Synonyms:(2R)-2-ammonio-3-hydroxypropanoate;(2R)-2-azaniumyl-3-hydroxypropanoate;2rcb;D-serine zwitterion;2v3u;CHEBI:35247

Chemical Property of (2R)-2-ammonio-3-hydroxypropanoate

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 220 °C
• Refractive Index: 1.4368 (estimate)
• Boiling Point: 394.8 °C at 760 mmHg
• PKA: 2.16±0.10(Predicted)
• Flash Point: 192.6 °C
• PSA: 83.55000
• Density: 1.415 g/cm³
• LogP: -0.90910
• Storage Temp.: Store at RT.
• Solubility.: H2O: 0.1 g/mL, clear, colorless
• Water Solubility.: 346 g/L (20 ºC)
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 105.042593085
• Heavy Atom Count: 7
• Complexity: 67.1

Purity/Quality:

98.0% min ^*data from raw suppliers

D-Serine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(C(=O)[O-])[NH3+])O
• Isomeric SMILES: C([C@H](C(=O)[O-])[NH3+])O
• Description: Serine is one of the 20 naturally-occurring amino acids used by all organisms in the biosynthesis of proteins. Having a single chiral center, serine can exist as one of two stereoisomers (L-Serine and D-Serine).D-serine is categorized as a nootropic. It is an amino acid found in the brain and is produced primarily in astrocytes; the conversion of L-serine to D-serine is catalyzed by the serine racemase enzyme. D-serine acts as a co-agonist of glutamate NMDA receptors and binds at the glycine site. NMDA receptors mediate synaptic plasticity, synaptogenesis, excitotoxicity, memory acquisition, and learning. Schizophrenia is characterized by reduced NMDA receptor signaling and therefore, D-serine supplementation has been tested extensively in patients with schizophrenia. It is thought to improve cognitive symptoms in this population. It is worth noting that in Alzheimer’s disease, there is excess glutamate receptor activation. Memantine, one of the drugs used to treat Alzheimer’s disease, is an NMDA receptor antagonist.
• Uses: A proteinogenic amino acids involved in the biosynthesis of purines and pyrimidines. Inhibitor of serine palmitoyltransferase. A neuromodulator. D-Serine is involved in the biosynthesis of purines, pyrimidines, and other amino acids. D-Serine also is an agonist of glycine site of the NMDA-type glutamate receptor. It also acts as Lacosamide intermediate. 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.

Technology Process of (2R)-2-ammonio-3-hydroxypropanoate

There total 82 articles about (2R)-2-ammonio-3-hydroxypropanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

pholipeptin → D-Serine (312-84-5,83245-15-2) + L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + (R)-leucine (328-38-1,21675-61-6,25248-98-0,70-45-1) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) + (2R)-aspartic acid (1783-96-6,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3)

Guidance literature:

With hydrogenchloride; at 120 ℃; for 20h; Product distribution;

DOI:10.1021/jo9603993

Reference yield:

ngercheumicin I → D-Serine (312-84-5,83245-15-2) + (2S,3S)-2-amino-3-hydroxybutanoic acid (28954-12-3,134357-96-3,7013-32-3,82822-12-6) + β-hydroxypalmitic acid (928-17-6,2398-34-7,20595-04-4,83780-74-9) + LEUCINE (328-39-2,21675-61-6,25248-98-0,70-45-1)

Guidance literature:

With hydrogenchloride; In water; at 110 ℃; for 20h;

DOI:10.3390/md11125051

Reference yield:

trichodepsipeptide A (1342309-23-2) → (R)-2-Hydroxy-3-methylbutyric acid (17407-56-6) + (S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) + D-Serine (312-84-5,83245-15-2) + L-serin (56-45-1,83245-15-2) + (R)-2-hydroxy-4-methylpentanoic acid (20312-37-2,498-36-2) + (S)-2-hydroxyl-3,3-dimethylbutyric acid (13748-90-8,498-36-2) + N-methyl-L-leucine (3060-46-6) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + N-methyl-D-leucine (31321-74-1) + D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6)

Guidance literature:

With hydrogenchloride; water; at 100 ℃; for 24h; Sealed tube;

DOI:10.1021/np2004243

upstream raw materials:

serin

N-chloroacetyl-D-serine

D-serine benzyl ester

(R)-2-(isoindolin-2-yl)-3-methoxypropanoic acid

Downstream raw materials:

3-hydroxy-2-oxopropionic acid

D-glyceric acid

N-(benzyloxycarbonyl)-D-serine

N-[(2,4-dichloro-phenoxy)-acetyl]-D-serine

Refernces

• 1、 Kim, Hee-Kwon,Park, Kyoung-Joo Jenny. "Novel practical synthesis of d-cycloserine". . p. 4090 - 4092. Retrieved 2012.
• 2、 Hawkinson, Jon E.,Acosta-Burruel, Manuel,Wood, Paul L.. "The metabotropic glutamate receptor antagonist L-2-amino-3-phosphonopropionic acid inhibits phosphoserine phosphatase". . p. 219 - 225. Retrieved 1996.
• 3、 Smith, Myron A.,Mack, Volker,Ebneth, Andreas,Moraes, Isabel,Felicetti, Brunella,Wood, Michael,Schonfeld, Dorian,Mather, Owen,Cesura, Andrea,Barker, John. "The structure of mammalian serine racemase: Evidence for conformational changes upon inhibitor binding". . p. 12873 - 12881. Retrieved 2010.
• 4、 Shin, Yern-Hyerk,Ban, Yeon Hee,Kim, Tae Ho,Bae, Eun Seo,Shin, Jongheon,Lee, Sang Kook,Jang, Jichan,Yoon, Yeo Joon,Oh, Dong-Chan. "Structures and Biosynthetic Pathway of Coprisamides C and D, 2-Alkenylcinnamic Acid-Containing Peptides from the Gut Bacterium of the Carrion Beetle Silpha perforata". . . Retrieved 2021/02/26.
• 5、 Chin, Jik,Fu, Rui,Lough, Alan J.,So, Soon Mog. "Hydrogen Bond Assisted l to d Conversion of α-Amino Acids". supporting information. p. 4335 - 4339. Retrieved 2020/02/11.