N-Acetyl-d-serine

Base Information

• Chemical Name: N-Acetyl-d-serine
• CAS No.: 152612-69-6
• Molecular Formula: C5H9NO4
• Molecular Weight: 147.131
• European Community (EC) Number: 604-864-5
• DSSTox Substance ID: DTXSID401316393
• Nikkaji Number: J425.587I
• Mol file: 152612-69-6.mol

Synonyms:N-Acetyl-d-serine;152612-69-6;(2R)-2-acetamido-3-hydroxypropanoic acid;(R)-2-acetamido-3-hydroxypropanoic acid;2-Acetylamino-3-hydroxy-propionic acid;Acetyl-D-serine;Ac-D-Ser-OH;D-Serine, N-acetyl-;SCHEMBL2122264;DTXSID401316393;AKOS006349344;(R)-2-acetamido-3-hydroxypropanoicacid;AM806412;CS-0139824;(R)-3-Hydroxy-2-(acetylamino)propanoic acid;W10597;EN300-2952177;A908026;359015-97-7

Chemical Property of N-Acetyl-d-serine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 86-89°C
• Boiling Point: 468.365oC at 760 mmHg
• PKA: 3.27±0.10(Predicted)
• Flash Point: 237.059oC
• PSA: 90.12000
• Density: 1.343g/cm3
• LogP: -0.59170
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 147.05315777
• Heavy Atom Count: 10
• Complexity: 145

Purity/Quality:

99% ^*data from raw suppliers

N-Acetyl-D-serine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CO)C(=O)O
• Isomeric SMILES: CC(=O)N[C@H](CO)C(=O)O
• Uses: N-Acetyl-D-serine is the modified amino acid D-Serine (S270975). D-Serine is a neurotransmitter that is concentrated in the mammalian brain, and is one of the very few amino acids that occur in the D- and L-configurations in significant amounts. D-Serine is an potent agonist of the N-methyl-D-aspartate (NMDA) receptor in the brain, which is associated with schizophrenia. Use of D-Serine has been considered as an additional therapy for refractory schizophrenic patients.

Technology Process of N-Acetyl-d-serine

There total 9 articles about N-Acetyl-d-serine 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: 100.0%

D-Serine (312-84-5,83245-15-2) + acetic anhydride (108-24-7) → (R)-2-acetamido-3-hydroxypropionic acid (152612-69-6)

Guidance literature:

With sodium hydrogencarbonate; In methanol; water; at 20 ℃; for 0.5h; Green chemistry;

Reference yield: 70.0%

(4R,5S,3'R)-1,5-dimethyl-3-(2'-acetamido-3'-hydroxypropionyl)-4-phenylimidazolidin-2-one (197232-68-1) → (R)-2-acetamido-3-hydroxypropionic acid (152612-69-6)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In water; N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1016/S0040-4039(97)01630-4

Reference yield:

N-acetyl-serine (97-14-3) → L-serin (56-45-1,83245-15-2) + (R)-2-acetamido-3-hydroxypropionic acid (152612-69-6)

Guidance literature:

With potassium hydroxide; potassium phosphate buffer; porcine kidney acylase I; at 40 ℃; relative initial rate of hydrolysis, also with Aspergillus acylase I as a catalyst; with or without CoCl₂;

DOI:10.1021/ja00198a055

upstream raw materials:

N-acetyl-serine

D-Serine

acetic anhydride

(4R,5S,3'R)-1,5-dimethyl-3-(2'-acetamido-3'-hydroxypropionyl)-4-phenylimidazolidin-2-one

Downstream raw materials:

(R)-N-4-(azido)benzyl 2-acetamido-3-methoxypropionamide

(R)-N-4-(azido)benzyl 2-acetamido-3-hydroxypropionamide

(R)-N-4-(amino)benzyl 2-acetamido-3-hydroxypropionamide

(R)-2-N-acetamido-3-methoxypropionic acid

Refernces

• 1、 -. "METHOD FOR PREPARING LACOSAMIDE". Paragraph 0030; 0031. . Retrieved 2016/12/01.
• 2、 Lee, Hyosung,Park, Ki Duk,Torregrosa, Robert,Yang, Xiao-Fang,Dustrude, Erik T.,Wang, Yuying,Wilson, Sarah M.,Barbosa, Cindy,Xiao, Yucheng,Cummins, Theodore R.,Khanna, Rajesh,Kohn, Harold. "Substituted N -(biphenyl-4′-yl)methyl (R)-2-acetamido-3- methoxypropionamides: Potent anticonvulsants that affect frequency (Use) dependence and slow inactivation of sodium channels". . p. 6165 - 6182. Retrieved 2014/08/18.