2788-84-3

Usage

Uses

Used in Pharmaceutical Industry:
L-Serine methyl ester is used as a chiral building block for the synthesis of various pharmaceuticals, agrochemicals, and natural products. Its unique stereochemistry allows for the creation of enantiomerically pure compounds, which are essential for the development of effective and safe drugs.
Used in Medicinal Chemistry:
L-Serine methyl ester is used as a research compound for studying its potential neuroprotective and antioxidant properties. Its ability to scavenge free radicals and protect cells from oxidative stress makes it a promising candidate for the development of therapies targeting neurodegenerative diseases and other conditions associated with oxidative stress.
Used in Drug Delivery Systems:
L-Serine methyl ester is used in the development of novel materials for drug delivery systems. Its unique properties can be leveraged to improve the efficiency, targeting, and bioavailability of therapeutic agents, potentially leading to more effective treatments for various diseases.
Used in Tissue Engineering Applications:
L-Serine methyl ester is investigated for its use in tissue engineering, where it can be incorporated into biomaterials to promote cell growth, differentiation, and tissue regeneration. Its potential to enhance the properties of engineered tissues makes it a valuable component in the development of advanced medical devices and regenerative therapies.

Upstream product

• 67-56-1 methanol 
• 56-45-1 L-serin 
• 69942-12-7 N-tert-butoxycarbonylserine methyl ester 
• 34143-74-3 1H,1H,2H,2H-Perfluorodecanethiol 
• 198836-50-9 N-(2-nitrobenzenesulfonyl)-L-serine methyl ester 
• 82911-78-2 N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester 
• 1169571-16-7 aspereline E 
• 2104-89-4 Ser-OMe 
• 5619-04-5 methyl 2-amino-3-hydroxypropanoate hydrochloride 
• 95715-86-9 (S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 312-84-5 D-Serine 
• 75-36-5 acetyl chloride 
• 93204-36-5 (R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate 
• 5874-57-7 R-(-)-serine methyl ester hydrochloride 

Downstream Products

• 76357-18-1 methyl 1-tritylaziridine-2-carboxylate 
• 108849-83-8 benzyloxycarbonyl-Gly-Ser-OMe 
• 56410-68-5 3-chloro-DL-alanine methyl ester 
• 25739-59-7 serine amide 
• 534-03-2 serinol 
• 101399-34-2 N-[N-(toluene-4-sulfonyl)-glycyl]-serine methyl ester 
• 56612-65-8 2-(3,5-dioxo-1,2-diphenyl-pyrazolidin-4-ylidene)-oxazolidine-4-carboxylic acid methyl ester 
• 58861-77-1 4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 55779-32-3 serine hydroxamate 
• 82679-63-8 3-Hydroxy-2-[(E)-3-phenyl-prop-2-en-(Z)-ylideneamino]-propionic acid methyl ester 
• 78479-32-0 2-((E)-2-Benzyloxycarbonylamino-but-2-enoylamino)-3-hydroxy-propionic acid methyl ester 
• 78464-22-9 2-((E)-2-Benzyloxycarbonylamino-3-phenyl-acryloylamino)-3-hydroxy-propionic acid methyl ester 
• 78464-19-4 2-((E)-2-Benzyloxycarbonylamino-pent-2-enoylamino)-3-hydroxy-propionic acid methyl ester 
• 78464-21-8 2-((E)-2-Benzyloxycarbonylamino-4-methyl-pent-2-enoylamino)-3-hydroxy-propionic acid methyl ester 

Relevant academic research and scientific papers

Synthesis and conformational analysis of poly(phenylacetylene)s with serinol-tethered carbohydrate appendages

We synthesized phenylacetylenes containing β-lactoside, β-cellobioside, or β-maltoside, and polymerized them to produce the corresponding poly (phenylacetylene)s. In these poly (phenylacetylene)s, the pendent carbohydrates were tethered to the mainchains

Chiral α-aminoxy acid/achiral cyclopropane α-aminoxy acid unit as a building block for constructing the α N-O helix

(Figure Presented) The monomer 1 derived from achiral 1-(aminoxy) cyclopropanecarboxylic acid (OAcc) and oligopeptides 2-9 consisting of a chiral α-aminoxy acid and an achiral α-aminoxy acid such as OAcc were synthesized and their structures characterized. The eight-membered-ring intramolecular hydrogen bond, namely the α N-O turn, was formed between adjacent residues independent of their chirality. However, the helix formation was sequence-dependent. Dipeptide 2 bearing chiral α-aminoxy acid (d-OAA) at the N-terminus and achiral OAcc at the C-terminus preferentially adopted a right-handed 1.88 helical structure, but dipeptide 3 (OAcc-d-OAA) did not. Theoretical calculation results, in good agreement with experimental ones, revealed that the biased handedness of α N-O turn found in OAcc residue depends on its preceding chiral residue. It was then found that the helical conformation was destroyed in the case of oligopeptides 6 and 7 [OAA-(OAcc) n, n = 2, 3]. The crystal structure of tripeptide 8 ( iPrCO-d-OVal-OAcc-d-OVal-NHiBu) further disclosed the helical structure formed by three consecutive homochiral α N-O turns. This study has uncovered achiral aminoxy acid residues such as the OAcc unit as a useful building block to be incorporated into chiral aminoxy peptides to mimic chiral helix structure.

Alcohol functionality in the fatty acid backbone of sphingomyelin guides the inhibition of blood coagulation

Cell-surface sphingomyelin (SM) inhibits binary and ternary complex activity of blood coagulation by an unknown mechanism. Here we show the OH functionality of SM contributes in forming the close assembly through intermolecular H-bond and through Ca2+ chelation, which restricts the protein-lipid/protein-protein interactions and thus inhibits the coagulation procedure.

N-Pyrazinoyl substituted amino acids as potential antimycobacterial agents-the synthesis and biological evaluation of enantiomers

Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis (Mtb), each year causing millions of deaths. In this article, we present the synthesis and biological evaluations of new potential antimycobacterial compounds containing a fragment of the first-line antitubercular drug pyrazinamide (PZA), coupled with methyl or ethyl esters of selected amino acids. The antimicrobial activity was evaluated on a variety of (myco)bacterial strains, including Mtb H37Ra, M. smegmatis, M. aurum, Staphylococcus aureus, Pseudomonas aeruginosa, and fungal strains, including Candida albicans and Aspergillus flavus. Emphasis was placed on the comparison of enantiomer activities. None of the synthesized compounds showed any significant activity against fungal strains, and their antibacterial activities were also low, the best minimum inhibitory concentration (MIC) value was 31.25 μM. However, several compounds presented high activity against Mtb. Overall, higher activity was seen in derivatives containing l-amino acids. Similarly, the activity seems tied to the more lipophilic compounds. The most active derivative contained phenylglycine moiety (PC-d/l-Pgl-Me, MIC 1.95 μg/mL). All active compounds possessed low cytotoxicity and good selectivity towards Mtb. To the best of our knowledge, this is the first study comparing the activities of the d- and l-amino acid derivatives of pyrazinamide as potential antimycobacterial compounds.

Liposomal FRET Assay Identifies Potent Drug-Like Inhibitors of the Ceramide Transport Protein (CERT)

Ceramide transfer protein (CERT) mediates non-vesicular transfer of ceramide from endoplasmic reticulum to Golgi apparatus and thus catalyzes the rate-limiting step of sphingomyelin biosynthesis. Usually, CERT ligands are evaluated in tedious binding assays or non-homogenous transfer assays using radiolabeled ceramides. Herein, a facile and sensitive assay for CERT, based on F?rster resonance energy transfer (FRET), is presented. To this end, we mixed donor and acceptor vesicles, each containing a different fluorescent ceramide species. By CERT-mediated transfer of fluorescent ceramide, a FRET system was established, which allows readout in 96-well plate format, despite the high hydrophobicity of the components. Screening of a 2 000 compound library resulted in two new potent CERT inhibitors. One is approved for use in humans and one is approved for use in animals. Evaluation of cellular activity by quantitative mass spectrometry and confocal microscopy showed inhibition of ceramide trafficking and sphingomyelin biosynthesis.

Nascent-HBr-Catalyzed Removal of Orthogonal Protecting Groups in Aqueous Surfactants

Organic reactions in the aqueous environment have recently emerged as a promising research area. The generation of nascent-HBr from the slow hydrolysis of the dispersed catalyst, benzyl bromide, with the interior water present in the hydrophobic core of the confined micellar medium in aqueous surfactant is described for the first time. The sustained-release nascent-HBr enabled the chemoselective cleavages of acid-sensitive orthogonal functionalities present in carbohydrates, amino alcohols, and hydroxylated acyclic compounds in good to excellent yields.

Catalytic Mechanism Study on the 1,2- and 1,4-Transfer Hydrogenation of Ketimines and β-Enamino Esters Catalyzed by Axially Chiral Biscarboline-Based Alcohols

Axial N-O alcohols, which have two large carboline moieties connected to the axis were synthesized and used in catalytic enantioselective 1,2- and 1,4-transfer hydrogenations of total 26 ketimines and β-enamino esters. Excellent levels of enantioselectivity ranging from 91% to 99% were achieved by using catalyst (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide. Interestingly, a mixture of (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide and (aR)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide was also able to provide high enantioselectivities up to 95% that is the same as that using pure (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide. A plausible catalytic mechanism was suggested and total four kinds of transition states (TS) including almost 60 TS structures were investigated using density functional theory (DFT) with different basis sets such as 6-311G(2d,p). The predicted activation energy data are consistent with the experimental results. (Figure presented.).

HETEROCYCLIC COMPOUNDS FOR THE TREATMENT OF ABNORMAL CELLULAR PROLIFERATION

This invention is in the area of heterocyclic-based compounds for the treatment of disorders involving abnormal cellular proliferation, including but not limited to tumors and cancers.

Glycosylated tris-bipyridine ferrous complexes as molecular mimics of densely packed glycoclusters on cell surfaces: spatial carbohydrate packing of glycoclusters changes on additions of salts

Tris-bipyridine ferrous complexes having β-lactosides, β-maltosides or α-mannosides with serinol spacers were prepared as molecular mimics of densely packed carbohydrate clusters on cell surfaces. Conformational analysis on these glycosylated complexes we

In situ formation of AuNPs using fatty N-acylamino hydrazide organogelators as templates

This work reports, for the first time, the synthesis of new fatty N-acylamino hydrazides and demonstrates the activity of these compounds as low-molecular-weight organic gelators and templates for preparation of gold nanoparticles (AuNPs). Initially, we evaluated the gelation properties of fatty N-acylamino hydrazides in various nonpolar and polar solvents (n-hexane, toluene, benzene, cyclohexane, and ethanol). Fatty N-acylamino hydrazide derived of the glycine and stearic acid (C18:0) did not form gels in any of the tested solvents. All other hydrazides did form gels in at least two of the organic solvents tested. The morphology of each gel was observed via scanning electron microscopy. The organogels derived from alanine, valine, and phenylalanine had translucid properties, while the serine organogels were opaque. Afterwards, the synthesis of AuNPs in the presence of the organogelator using microwave irradiation was realized. Organogelator agents reduced HAuCl4 showing plasmon band peaks between 530 and 543 nm. In addition, the method does not require a reducing agent, which is typically a potential source of contamination and toxicity. Therefore, this work confirms the importance of the hydrazide group of the new fatty N-acylamino hydrazides in gel formation and as organogelator agents for preparation of AuNPs.