16820-18-1

Basic information

• Product Name: 2-Methyl-L-serine
• Synonyms: (+)-2-Methyl-L-serine;ALPHA-METHYL-D-SER;(R)-3-HYDROXY-2-METHYLALANINE;L-Serine, 2-methyl- (9CI);-Methyl-D-Ser;A-METHYL-D-SER ;(s)-(+)-2-amino-3-hydroxy-2-methylpropionic acid;L-α-methylserine
• CAS NO: 16820-18-1
• Molecular Formula: C4H9NO3
• Molecular Weight: 119.12
• EINECS: 226-565-5
• Product Categories: GLYCINESCAFFOLD;Amino Acid Derivatives;Serine [Ser, S];Aliphatics;Amino Acids & Derivatives;unnatural amino acids
• Mol File: 16820-18-1.mol
• Article Data: 29

Chemical Properties

• Melting Point: 286-288 °C
• Boiling Point: 222.38°C (rough estimate)
• Flash Point: 162.9oC
• Appearance: White/Powder
• Density: 1.3126 (rough estimate)
• Vapor Pressure: 3.77E-06mmHg at 25°C
• Refractive Index: 1.4183 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly, Heated), Water (Slightly)
• PKA: 2.20±0.10(Predicted)
• CAS DataBase Reference: 2-Methyl-L-serine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-L-serine(16820-18-1)
• EPA Substance Registry System: 2-Methyl-L-serine(16820-18-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-37/39-26
• Hazardous Substances Data: 16820-18-1(Hazardous Substances Data)

Usage

Description

2-Methyl-L-serine is an organic compound that serves as a potential chiral building block for the synthesis of various α-methyl α-amino acids. It is characterized by its white powder form and holds significant value in the field of chemical synthesis.

Uses

Used in Pharmaceutical Industry:
2-Methyl-L-serine is used as a chiral building block for the synthesis of different α-methyl α-amino acids, which are essential components in the development of various pharmaceutical compounds. Its unique structure allows for the creation of novel drugs with improved efficacy and selectivity.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Methyl-L-serine is utilized as a key component in the production of various α-methyl α-amino acids. These amino acids are crucial for the development of new molecules with specific properties and applications, such as in the creation of novel drugs, agrochemicals, and other specialty chemicals.
Used in Research and Development:
2-Methyl-L-serine is also employed in research and development settings, where it is used to study the properties and behavior of chiral compounds. Its unique structure makes it an ideal candidate for exploring the effects of chirality on molecular interactions and reactivity, leading to a deeper understanding of stereochemistry and its implications in various fields.

InChI:InChI=1/C4H9NO3/c1-4(5,2-6)3(7)8/h6H,2,5H2,1H3,(H,7,8)/t4-/m0/s1

Upstream product

• 16820-14-7 5-hydroxymethyl-5-methyl-imidazolidine-2,4-dione 
• 50-00-0 formaldehyd 
• 56-41-7 L-alanin 
• 96293-17-3 (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide 
• 117176-06-4 (S)-4-Methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 93250-94-3 (2R,4S)-methyl 2-tert-butyl-3-formyl-4-methyloxazolidine-4-carboxylate 
• 72953-33-4 (3R,6S)-Hydroxymethyl-2,5-dimethoxy-3,6-dimethyl-3,6-dihydropyrazin 
• 7508-94-3 2-Acetylamino-3-hydroxy-2-methyl-propionic acid 
• 121704-29-8 3-Hydroxy-2-(2-methoxy-acetylamino)-2-methyl-propionic acid 
• 657401-76-8 methyl hydrogen 2-(<(tert-butyl)dimethylsilyl>oxymethyl)-2-methylmalonate 
• 151075-00-2 (+)-(2S)-N-(3'-Hydroxypropyl)-3-hydroxy-2-methyl-2-<(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>propionamide 
• 168553-64-8 (S)-3-Benzyloxy-2-methyl-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionic acid 
• 211188-29-3 (2S)-3-hydroxy-2-(N-benzyloxyamino)-2-methylpropionic acid 
• 298704-91-3 (3S,6R)-N-1-(tert-butoxycarbonyl)-3-hydroxymethyl-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone 

Downstream Products

• 84311-19-3 (S)-2-tert-Butoxycarbonylamino-3-hydroxy-2-methyl-propionic acid 
• 84311-18-2 (R)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxy-propanoic acid 
• 188476-33-7 (S)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxypropanoic acid methyl ester 
• 188476-28-0 (R)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxypropanoic acid methyl ester 
• 179862-73-8 N-(t-butoxycarbonyl)-α-methylserine benzyl ester 
• 147316-32-3 (2S)-methyl 2-amino-3-hydroxy-2-methylpropanoate 
• 72953-37-8 methyl (R)-(+)-2-amino-3-hydroxy-2-methylpropionate 
• 114396-70-2 (S)-N-Cbz-α-MeSer(OH)-OH 
• 50-00-0 formaldehyd 
• 56-41-7 L-alanin 
• 1201590-90-0 C₁₃H₂₇NO₃Si 
• 1392494-40-4 Fmoc-Ala-(S)-(αMe)Ser(ΨH,HPro)-OH 
• 1392494-44-8 Z-(S)-(αMe)Ser(ΨH,HPro)-OH 
• 1392494-37-9 Fmoc-Ala-(R)-(αMe)Ser(ΨH,HPro)-OH 

Relevant articles and documents

Method for preparing 2-methylserine

The invention relates to a method for preparing 2-methylserine, and mainly solves the technical problem of being long in route, complicated in operation, and not conducive to mass production of the existing synthetic method. The method comprises the following steps: Cbz-chiral alanine and Benzaldehyde dimethyl acetal are reacted under the action of thionyl chloride and zinc chloride, a reaction product is crystallized to obtain an intermediate 1, the intermediate 1 is reacted under cooperation of an alkaline reagent to obtain an intermediate 2, an intermediate 3 is obtained from the intermediate 2 by the action of lithium hydroxide, and the final product 2-methylserine is obtained from the intermediate 3 by palladium carbon catalytic hydrogenolysis. High purity 2-methylserine can be obtained by the method.

Cloning of the gene encoding α-methylserine hydroxymethyltransferase from Aminobacter sp. AJ110403 and Ensifer sp. AJ110404 and characterization of the recombinant enzyme

Genes encoding α-methylserine hydroxymethyltransferase from Aminobacter sp. AJ110403 and Ensifer sp. AJ110404 were cloned and expressed in Escherichia coli. The purified enzymes were homodimers with a 46-kDa subunit and contained 1 mol/mol-subunit of pyridoxal 5′-phosphate. The V max of these enzymes catalyzing the conversion of α-methyl-L-serine to D-alanine via tetrahydrofolate was 22.1 U/mg (AJ110403) and 15.4 U/mg (AJ110404).

Stereoselective addition of organometallic reagents to a chiral acyclic nitrone derived from L-erythrulose

The additions of various organolithium and organomagnesium reagents to a chiral nitrone prepared from L-erythrulose took place with variable diastereoselectivity. The degree and strength of the facial selectivity can be modified if the reaction is performed in the presence of Lewis acid additives: zinc bromide enhances the attack to the Si face of the C=N bond whereas diethyl aluminium chloride promotes attack to the Re face. The obtained adducts can be then transformed into protected N-hydroxy-α,α-disubstituted-α- amino acid derivatives as well as into the corresponding α,α- disubstituted α-amino acids.