19794-53-7

Usage

Uses

Used in Pharmaceutical Industry:
DL-O-METHYLSERINE is used as a reagent for the synthesis of D-serine transporter inhibitors. These inhibitors are crucial in the treatment of visual system disorders and the enhancement of visual functions. By modulating the transport of D-serine, a neurotransmitter involved in the functioning of the visual system, DL-O-METHYLSERINE contributes to the development of therapeutic agents that can improve vision and address related disorders.

InChI:InChI=1/C4H9NO3/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)

Upstream product

• 98632-99-6 O-Methyl-N-acetyl-DL-serine 
• 51293-45-9 O-methyl-N,N-phthaloyl-L-serine 
• 98026-05-2 α-amino-β-methoxy-propionamide 
• 2544-05-0 2-chloro-3-methoxy propanoic acid 
• 65090-78-0 α-bromo-β-methoxypropanoic acid 
• 27704-96-7 methyl 2-bromo-3-methoxypropionate 
• 1356449-88-1 calyxamide B 
• 1356449-87-0 calyxamide A 
• 1190855-79-8 neomastoidin A 
• 124-41-4 sodium methylate 

Downstream Products

• 56-45-1 L-serin 
• 86096-33-5 N-Chloroacetyl-dl-O-methylserine 
• 51293-47-1 N-tert-butoxycarbonyl-(S)-O-methyl-serin 
• 86118-11-8 D-o-methylserine 
• 98632-99-6 O-Methyl-N-acetyl-DL-serine 
• 61493-99-0 DL-N-(3-Methoxycarbamoyl-5-nitrobenzoyl)-O-methylserin 
• 64356-74-7 N-(benzyloxycarbonyl)-O-methyl-DL-serine 
• 196601-69-1 (R)-2-amino-N-benzyl-3-methoxypropanamide 
• 474534-78-6 (S)-N-benzyl-2-amino-3-methoxypropionamide 
• 121470-74-4 N-benzoyl-DL-O-methylserine 
• 1800300-79-1 methyl 2-amino-3-methoxypropionoate hydrochloride 
• 3183-36-6 N-Dichloracetyl-O-methyl-DL-serin 
• 88642-84-6 O³-DL-Methylserin-methylester 
• 91248-69-0 O-methyl-N-(toluene-4-sulfonyl)-serine 

Relevant academic research and scientific papers

Synthesis method of O-methyl-D-serine

The invention discloses a synthesis method of O-methyl-D-serine. The synthesis method includes the following steps that 1, acrylic acid methyl ester is added into a reaction bottle, after the temperature is raised, bromine is dropwise added, after an addition reaction is conducted, decompression and distillation are conducted to remove excessive bromine, methyl alcohol is added to residues, after the temperature is lowered, sodium methylate is added, after an alcoholysis reaction, decompression and distillation are conducted to remove methyl alcohol, ammonium hydroxide is added, after an ammonium hydroxide, concentrated crystallization is conducted, and O-methyl-DL-serine is obtained; 2, acetic acid is added into the reaction bottle, the O-methyl-DL-serine, D-tartaric acid and salicylaldehyde are added in sequence, after the temperature is raised for a reaction, cooling and crystallization are conducted, separation is conducted, and O-methyl-D-serine double salt is obtained; 3, the O-methyl-D-serine double salt is dissolved in a methyl alcohol aqueous solution, ammonium hydroxide is added to regulate PH to be 7-8, crystallization and separation are conducted, and the O-methyl-D-serine is obtained. The synthesis method is mild in reaction temperature, safe to operate, low in cost and high in chirality purity, and raw materials are easy to obtain.

An efficient chemoenzymatic method to prepare optically active O-methyl-l-serine

O-Methyl-l-serine and its derivatives are relevant in peptide synthesis (food, pharmaceuticals, and cosmetics). Optically active O-methyl-l-serine was prepared using a chemoenzymatic method from inexpensive acrylamide. Our method is a four step reaction sequence; bromination of acrylamide; etherification of dibromopropionamide; ammonolysis of α-bromo-β-methoxy-propionamide; enzymatic racemization; and selective hydrolysis. The double-enzyme catalyst system, which consists of α-amino-*-caprolactam racemase (Locus, E01594) and peptidase B (Locus, D84499), was successfully applied to produce enantiopure O-methyl-l-serine (ee >99.9%) in high yield (>99.7%). Optically active O-methyl-l-serine was obtained with a total yield of 82.4%.

PROCESS FOR PREPARING LACOSAMIDE

The present invention provides a process for the preparation of lacosamide in substantially optically pure form, which in one aspect comprises the following steps: (i) resolution of O-methyl-D,L-serine to provide O-methyl-D-serine in substantially optically pure form; (ii) acetylation of O-methyl-D-serine thereby obtained to provide the N-acetyl 10 derivative thereof in substantially optically pure form; (iii) activating the carboxy group of the compound thereby obtained; and (iv) reacting the compound thereby obtained with benzylamine.

Calyxamides A and B, cytotoxic cyclic peptides from the marine sponge Discodermia calyx

Cyclic peptides containing 5-hydroxytryptophan and thiazole moieties were isolated from the marine sponge Discodermia calyx collected near Shikine-jima Island, Japan. The structures of calyxamides A (1) and B (2), including the absolute configurations of all amino acids, were elucidated by spectroscopic analyses and degradation experiments. The structures are similar to keramamides F and G, previously isolated from Theonella sp. The analysis of the 16S rDNA sequences obtained from the metagenomic DNA of D. calyx revealed the presence of Candidatus Entotheonella sp., an unculturable δ-proteobacterium inhabiting the Theonella genus and implicated in the biosynthesis of bioactive peptides.

Neomastoidin A, a novel monoacylglycerol with an amino acid moiety from Macrolepiota neomastoidea

A novel monoacylglycerol with an amino acid moiety, neomastoidin A (1), was isolated from the fruiting bodies of the poisonous mushroom Macrolepiota neomastoidea. The structure of 1 was established by extensive spectroscopic analysis and further confirmed

Process for producing beta-1, 3-n-acetylglucosamine transferase and n-acetylglucosamine- containing composite saccharide

The present invention can provide a process for producing a protein having β1,3-N-acetylglucosaminyltransferase activity using a transformant comprising a DNA encoding a protein having β1,3-N-acetylglucosaminyltransferase activity derived from a microorganism belonging to the genus Pasteurella and a process for producing an N-acetylglucosamine-containing complex carbohydrate using a transformant capable of producing a protein having β1,3-N-acetylglucosaminyltransferase activity derived from a microorganism.

METHOD OF SEARCHING SUBSTANE HAVING ANTIDIABETIC ACTIVITY

The present invention provides a screening method of a substance which inhibits binding of a condensed purine derivative to a pancreatic β cell or a treated product of the cell, a substance which inhibits binding of a condensed purine derivative to a protein capable of the condensed purine derivative, and a substance which inhibits the expression or enzymatic activity of a protein capable of a condensed purine derivative, which comprises using the condensed purine derivative and a pancreatic β cell or a treated product of the cell or a protein capable of binding to the condensed purine derivative.

Process for producing alpha 2,3/ alpha 2,8-sialyltransferase and sialic acid-containing complex sugar

The present invention can provide a process for producing a protein having α2,3/α2,8-sialyltransferase activity using a transformant comprising a DNA encoding a protein having α2,3/α2,8-sialyltransferase activity derived from a microorganism belonging to the genus Pasteurella and a process for producing a sialic acid-containing complex carbohydrate using a transformant capable of producing a protein having α2,3/α2,8-sialyltransferase activity derived from a microorganism.

Beta1, 3-galactose transferase and dna encoding the enzyme

The present invention provides a protein having β1,3-galactosyltransferase activity, a DNA encoding the protein, a transformant comprising the DNA, a process for producing the protein using the transformant, and a process for producing a galactose-containing complex carbohydrate using the transformant.