16354-58-8

Basic information

• Product Name: N-Acetyl-L-serine
• Synonyms: N-Acetyl-L-serine;(2S)-2-acetamido-3-hydroxy-propanoic acid;N-Acetylserine;N-Ac-L-Ser-OH;L-Serine, N-acetyl-;(S)-2-AcetaMido-3-hydroxypropanoic acid
• CAS NO: 16354-58-8
• Molecular Formula: C₅H₉NO₄
• Molecular Weight: 147.13
• Mol File: 16354-58-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 207.6℃
• Boiling Point: 468.4°Cat760mmHg
• Flash Point: 237.1°C
• Appearance: /
• Density: 1.343g/cm³
• Vapor Pressure: 9.68E-11mmHg at 25°C
• Refractive Index: 1.494
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly, Sonicated), Methanol (Sparingly), Water (Sparingly)
• PKA: 3.27±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: N-Acetyl-L-serine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-L-serine(16354-58-8)
• EPA Substance Registry System: N-Acetyl-L-serine(16354-58-8)

Safety Data

• Hazardous Substances Data: 16354-58-8(Hazardous Substances Data)

Usage

Uses

N-Acetyl-L-serine (cas# 16354-58-8) was useful for studying wheat drought tolerance.

Definition

ChEBI: An N-acetyl-L-amino acid in which the amino acid specified is L-serine. Metabolite observed in cancer metabolism.

InChI:InChI=1/C5H9NO4/c1-3(8)6-4(2-7)5(9)10/h4,7H,2H2,1H3,(H,6,8)(H,9,10)

Synthetic route

D,L-serine hydrochloride (16428-75-4, 51221-50-2) + acetyl chloride (75-36-5) → N-acetyl-L-serine (16354-58-8)

Conditions	Yield
With triethylamine In dichloromethane at 4℃; for 4.5h; Time;	85%

L-serin (56-45-1) + acetic anhydride (108-24-7) → N-acetyl-L-serine (16354-58-8)

Conditions	Yield
With sodium hydroxide In water for 4h; pH=10;	81.1%
With sodium hydroxide
With acetic acid for 24h; Ambient temperature;
In acetic acid at 20℃;

tetrachloromethane (56-23-5) + L-serin (56-45-1) + acetic anhydride (108-24-7) → N-acetyl-L-serine (16354-58-8)

Conditions	Yield
at 0 - 5℃;

O-acetyl-L-serine (5147-00-2) → N-acetyl-L-serine (16354-58-8)

Conditions	Yield
In water at 30℃; Rate constant; phosphate buffer pH 8.03-8.91, μ=0.5 (KCl);

2-[(Z)-(R)-2-Acetylamino-2-carboxy-ethoxyimino]-pentanedioic acid (114118-71-7) → Glutamic acid (617-65-2) + N-acetyl-L-serine (16354-58-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal

2-[(E)-(S)-2-Acetylamino-2-carboxy-ethoxyimino]-pentanedioic acid (114118-71-7) → Glutamic acid (617-65-2) + N-acetyl-L-serine (16354-58-8)

Conditions	Yield
With hydrogen; platinum In acetic acid Product distribution;

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) + acetic acid (64-19-7) → N-acetyl-L-serine (16354-58-8)

Conditions	Yield
With triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 5h;

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) + acetyl chloride (75-36-5) → N-acetyl-L-serine (16354-58-8)

Conditions	Yield
With triethylamine In ethanol; chloroform

L-serin (56-45-1) + acetic anhydride (108-24-7) → N-acetyl-L-serine (16354-58-8) + N,O-D-diacetyl serine (2233-54-7)

Conditions	Yield
With acetic acid for 18h;

(S)-methyl 2-acetamido-3-hydroxypropanoate (2311-26-4, 54322-41-7, 55299-56-4) → N-acetyl-L-serine (16354-58-8)

Conditions	Yield
With water; lithium hydroxide In methanol for 0.5h;	15 mg

methyl bromide (74-83-9) + N-acetyl-L-serine (16354-58-8) → (RS)-2-acetylamino-3-methoxypropionic acid methyl ester

Conditions	Yield
With sodium hydride In tetrahydrofuran at 60℃; for 5h; Solvent; Reagent/catalyst;	90%

N-acetyl-L-serine (16354-58-8) + L-alanine methyl ester hydrochloride (2491-20-5) → N-acetyl-L-serinyl-L-alanine methyl ester

Conditions	Yield
With diethylphosphoryl-glyceroacetonide-Oxyma; sodium hydrogencarbonate In N,N-dimethyl-formamide for 2h;	85%

N-acetyl-L-serine (16354-58-8) + 1-isocyanato-2-methyl-3-nitrobenzene → N-acetyl-O-[(3-nitro-2-methylphenyl)carbamoyl]-serine

Conditions	Yield
In pyridine at 80℃; for 3h;	81%

N-acetyl-L-serine (16354-58-8) + 2-methyl-5-nitrophenyl isocyanate (13471-68-6) → N-acetyl-O-[(5-nitro-2-methylphenyl)carbamoyl]-serine

Conditions	Yield
In pyridine at 80℃; for 3h;	75%

N-acetyl-L-serine (16354-58-8) + Artenimol → C21H33NO8

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether at -5℃; for 19.5h;	75%

N-acetyl-L-serine (16354-58-8) + (9H-fluoren-9-yl)methyl ((S)-4-amino-5-(((S)-1-amino-4-methyl-1-oxopentan-2-yl)amino)-5-oxopentyl)carbamate → (9H-fluoren-9-yl)methyl ((S)-4-((S)-2-acetamido-3-hydroxypropanamido)-5-(((S)-1-amino-4-methyl-1-oxopentan-2-yl)amino)-5-oxopentyl)carbamate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 12h; Inert atmosphere;	75%

N-acetyl-L-serine (16354-58-8) + 3-nitro-4-methylphenyl isocyanate (13471-69-7) → N-acetyl-O-[(3-nitro-4-methylphenyl)carbamoyl]-serine

Conditions	Yield
In pyridine at 80℃; for 3h;	70%

N-acetyl-L-serine (16354-58-8) + (S)-(9H-fluoren-9-yl)methyl (5,6-diamino-6-oxohexyl)carbamate → (9H-fluoren-9-yl)methyl ((S)-5-((S)-2-acetamido-3-hydroxypropanamido)-6-amino-6-oxohexyl)carbamate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;	70%

N-acetyl-L-serine (16354-58-8) + trityl chloride (76-83-5) → (S)-2-Acetylamino-3-trityloxy-propionic acid (906666-20-4)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 12h;	65.3%

N-acetyl-L-serine (16354-58-8) + (S)-(9H-fluoren-9-yl)methyl (4-amino-5-((1-carbamoylcyclopentyl)amino)-5-oxopentyl)carbamate → (9H-fluoren-9-yl) methyl ((S)-4-((S)-2-acetamido-3-hydroxypropanamido)-5-((1-carbamoylcyclopentyl)amino)-5-oxopentyl)carbamate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 12h; Inert atmosphere;	46%

diazomethane (186581-53-3, 908094-01-9) + N-acetyl-L-serine (16354-58-8) → (S)-methyl 2-acetamido-3-hydroxypropanoate (2311-26-4, 54322-41-7, 55299-56-4)

Conditions	Yield
In methanol; diethyl ether

N-acetyl-L-serine (16354-58-8) → Ac-Ser-NHNH2 (7721-87-1)

Conditions	Yield
(i) MeOH, HCl, (ii) N2H4; Multistep reaction;

N-acetyl-L-serine (16354-58-8) + (S)-3-Amino-N-[(S)-1-((S)-1-{(S)-2-methyl-1-[N'-(2,2,2-trichloro-ethoxycarbonyl)-hydrazinocarbonyl]-propylcarbamoyl}-ethylcarbamoyl)-ethyl]-succinamic acid benzyl ester → Ac-Ser-Asp(OBzl)-Ala-Ala-Val-NHNH-Troc (134327-75-6)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 4℃; for 8h; Yield given;

N-acetyl-L-serine (16354-58-8) + H-Asp(OBzl)-Ala-Ala-Val-ONb → Ac-Ser-Asp(OBzl)-Ala-Ala-Val-ONb (77313-52-1)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In water; N,N-dimethyl-formamide at 0℃; Yield given;

N-acetyl-L-serine (16354-58-8) → L-serin (56-45-1)

Conditions	Yield
With Aspergillus oryzae acylase relative rates;

N-acetyl-L-serine (16354-58-8) + 1-bromomethyl-4-nitro-benzene (100-11-8) → (S)-2-Acetylamino-3-hydroxy-propionic acid 4-nitro-benzyl ester (119144-08-0)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 3h; Ambient temperature;

N-acetyl-L-serine (16354-58-8) + benzylamine (100-46-9) → (S)-N-Benzyl 2-Acetamidohydracrylamide (171623-03-3)

Conditions	Yield
With 4-methyl-morpholine; isobutyl chloroformate 1.) THF, -78 deg C, 2 min, 2.) THF, RT, 30 min; Yield given. Multistep reaction;

N-acetyl-L-serine (16354-58-8) + N-α-9-fluorenylmethoxycarbonyl-aspartic acid (136083-57-3, 136083-73-3, 119062-05-4) + C22H25N3O3 + H-Pro-2-chlorotrityl resin → C21H35N5O9

Conditions	Yield
Multistep reaction;

N-acetyl-L-serine (16354-58-8) → N-(3,4-dihydroxyphenethyl)-2-acetamido-3-hydroxypropanamide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 65.3 percent / triethylamine / CH2Cl2 / 12 h / 20 °C 2.1: 1-hydroxybenzotriazole; 2-dimethylaminoisopropyl chloride hydrochloride / dimethylformamide / 2 h 2.2: 73.7 percent / potassium carbonate / dimethylformamide / 12 h / 20 °C 3.1: 63.2 percent / trifluoroacetic acid / CH2Cl2 / 2 h / 20 °C View Scheme

N-acetyl-L-serine (16354-58-8) → 2-acetylamino-N-[2-(3,4-dihydroxy-phenyl)-ethyl]-3-trityloxy-propionamide (906666-21-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 65.3 percent / triethylamine / CH2Cl2 / 12 h / 20 °C 2.1: 1-hydroxybenzotriazole; 2-dimethylaminoisopropyl chloride hydrochloride / dimethylformamide / 2 h 2.2: 73.7 percent / potassium carbonate / dimethylformamide / 12 h / 20 °C View Scheme

Upstream product

• 56-23-5 tetrachloromethane 
• 56-45-1 L-serin 
• 108-24-7 acetic anhydride 
• 5147-00-2 O-acetyl-L-serine 
• 16428-75-4 D,L-serine hydrochloride 
• 75-36-5 acetyl chloride 
• 2311-26-4 (S)-methyl 2-acetamido-3-hydroxypropanoate 
• 5680-80-8 methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride 
• 64-19-7 acetic acid 
• 114118-71-7 2-[(E)-(S)-2-Acetylamino-2-carboxy-ethoxyimino]-pentanedioic acid 
• 114118-71-7 2-[(Z)-(R)-2-Acetylamino-2-carboxy-ethoxyimino]-pentanedioic acid 

Downstream Products

• 134327-75-6 Ac-Ser-Asp(OBzl)-Ala-Ala-Val-NHNH-Troc 
• 77313-52-1 Ac-Ser-Asp(OBzl)-Ala-Ala-Val-ONb 
• 56-45-1 L-serin 
• 906666-20-4 (S)-2-Acetylamino-3-trityloxy-propionic acid 
• 1197983-02-0 (S)-N-4-(amino)benzyl 2-acetamido-3-hydroxypropionamide 
• 134304-89-5 Ac-Ser-Asp(OBzl)-Ala-Ala-Val-NHNH₂ 
• 77313-53-2 Ac-Ser-Asp(OBzl)-Ala-Ala-Val-OH 
• 175481-36-4 (2S)-2-(acetylamino)-N-benzyl-3-methoxypropanamide 
• 906666-21-5 2-acetylamino-N-[2-(3,4-dihydroxy-phenyl)-ethyl]-3-trityloxy-propionamide 
• 171623-03-3 (S)-N-Benzyl-2-acetamidohydracrylamide 
• 119144-08-0 (S)-2-Acetylamino-3-hydroxy-propionic acid 4-nitro-benzyl ester 
• 2311-26-4 (S)-methyl 2-acetamido-3-hydroxypropanoate 

Relevant articles and documents

Intramolecular Aminolysis of Esters. O-Acetylserine and γ-Esters of Glutamic Acid

The kinetics of the concurrent hydrolysis and intramolecular aminolysis of γ-ethyl glutamate have been studied in aqueous solution (40 deg C) in range of pH 7.6-10.4.While hydrolysis contributes only 3percent to the overall rate of reaction of γ-ethyl glutamate at pH 10.4, its importance relative to aminolysis increases with decreasing pH; at pH 8, the hydrolysis pathway accounts for 32percent of the rate of disapperance of the ester.The pH-rate profile for the aminolysis pathway indicates the presence of water and a hydroxide-catalyzed reaction and provides no evidence for intermediates.The conversion of diethyl glutamate to pyrrolidone-5-carboxylate may occur through either of two competing pathways: (a) rate-determining aminolysis to ethyl pyrrolidone-5-carboxylate, followed by rapid hydrolysis of the ester; (b) rate-determining hydrolysis to γ-ethylglutamate, followed by rapid cyclization.The pH-rate profile for the intramolecular aminolysis of O-acetylserine, determined at zero buffer concentration (30 deg C), has the complex appearance characteristic for acyl-transfer reactions involving neutral and anionic tetrahedral intermediates.Quantitative support for the interpretation of the pH-rate profile comes from the analysis of the nonlinear increases in the rate of aminolysis observed in the presence of increasing concentrations of phosphate buffers.The results of this and earlier studies suggest that there may not be major differences in the mechanisms of the intra- and intermolecular aminolysis of weakly acidic alcohols.

GRANZYME B DIRECTED IMAGING AND THERAPY

Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.

CHEMOSELECTIVE ENRICHMENT FOR COMPOUND ISOLATION

Chemoselective isolation of aliphatic hydroxyl group-containing and aromatic hydroxyl group-containing compounds is accomplished via formation of polymeric siloxyl ethers. Chemoselective release of aliphatic hydroxyl group-containing and aromatic hydroxyl group-containing compounds from polymeric siloxyl reagents is described.