4829-14-5

Usage

Uses

Used in Pharmaceutical Industry:
D-Alanine N-carboxyanhydride is used as a reagent for the synthesis of poly(alanine), which is an important component in the development of various pharmaceutical compounds. It is particularly useful in the creation of peptidomimetics, which are synthetic compounds that mimic the structure and function of natural peptides.
Used in Polymer Industry:
D-Alanine N-carboxyanhydride is used as a modifier in the production of poly(ethylene glycol) (PEG) and l-poly(alanine-co-phenylalanine). These modified polymers have a range of applications, including drug delivery systems, where they can improve the solubility, stability, and bioavailability of therapeutic agents.
Used in Antibiotic Synthesis:
D-Alanine N-carboxyanhydride is used as a key intermediate in the synthesis of certain antibiotics, such as vancomycin and teicoplanin. These antibiotics are effective against gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and other drug-resistant strains.
Used in Peptidoglycan Synthesis:
D-Alanine N-carboxyanhydride is also used in the synthesis of peptidoglycan, a major component of bacterial cell walls. D-Alanine N-carboxyanhydride plays a crucial role in the development of new antimicrobial agents targeting bacterial cell wall synthesis, which can help combat antibiotic resistance.

Upstream product

• 75-44-5 phosgene 
• 338-69-2 D-Alanine 
• 26607-51-2 N-benzyloxycarbonyl-D-alanine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 3744-87-4 Boc-(R)-Ala 
• 302-72-7 rac-Ala-OH 
• 4132-86-9 N-benzyloxycarbonylalanine 
• 34653-64-0 N-ethoxycarbonyl-DL-alanine trimethylsilanyl ester 
• 2899-44-7 N,O-bis(trimethylsilyl)-α-alanine 
• 77340-50-2 N-carbamoyl-DL-alanine 
• 56-41-7 L-alanine 
• 15761-38-3 L-N-Boc-Ala 

Downstream Products

• 129288-48-8 (R)-benzyl 4-methyl-2,5-dioxooxazolidine-3-carboxylate 
• 124491-96-9 (RS)-alanine N,N-dimethylamide 
• 86211-51-0 D,L-alanine cyclohexylamide 
• 34582-44-0 5-Cyclohexyl-2-methylhydantoinsaeure 
• 34582-46-2 2-(3-Benzyl-ureido)-propionic acid 
• 2508-25-0 DL-alanine hydroxamic acid 
• 5265-18-9 (+/-)-cathinone 

Relevant academic research and scientific papers

Capsidone artificial hapten, artificial antigen and preparation method and application thereof

The invention relates to the field of cathinone artificial antigen structures, and particularly relates to a cathinone artificial antigen, an artificial antigen as well as a preparation method and application thereof. The cathinone artificial antigen is characterized in that a molecular structural formula of the cathinone artificial antigen is shown as follows: the formula (1) is shown in the description. According to the cathinone artificial antigen provided by the invention, a connecting arm is introduced onto a site N of cathinone, and the connecting arm is introduced onto the decoration site so that a characteristic structure of the cathinone is kept to a maximum extent; moreover, the cathinone artificial antigen has an active group coupled with carrier protein and can be used as an antigen determinant group. Compared with an annular connecting arm, the connecting arm adopted by the invention is chain-shaped, an identification degree of T cells to the connecting arm can be reducedas much as possible during immunization, so that an antibody obtained by immunization has higher specificity and affinity to the cathinone.

Improved Scale-up Synthesis and Purification of Clinical Asthma Candidate MIDD0301

We report an improved and scalable synthesis of MIDD0301, a positive GABAA receptor modulator that is under development as oral and inhaled treatments for asthma. In contrast to other benzodiazepines in clinical use, MIDD0301 is a chiral compound that has limited brain absorption. The starting material to generate MIDD0301 is 2-amino-5-bromo-2′-fluorobenzophenone, which has a nonbasic nitrogen due to electron-withdrawing substituents in the ortho and para positions, reducing its reactivity toward activated carboxylic acids. Investigations of peptide coupling reagents on a multigram scale resulted in moderate yields due to incomplete conversions. Second, the basic conditions used for the formation of the seven-membered 1,4-diazepine ring resulted in racemization of the chiral center. We found that neutral conditions comparable to the pKa of the primary amine were sufficient to support the formation of the intramolecular imine but did not enable the simultaneous removal of the protecting group. Both difficulties were overcome with the application of the N-carboxyanhydride of d-alanine. Activated in the presence of an acid, this compound reacted with nonbasic 2-amino-5-bromo-2′-fluorobenzophenone and formed the 1,4-diazepine upon neutralization with triethylamine. Carefully designed workup procedures and divergent solubility of the synthesic intermediates in solvents and solvent combinations were utilized to eliminate the need for column chromatography. To improve compatibility with large-scale reactors, temperature-controlled slow addition of reagents generated the imidazodiazepine at -20 °C. All intermediates were isolated with a purity of >97% and impurities were identified and quantified. After the final hydrolysis step, MIDD0301 was isolated in a 44% overall yield and a purity of 98.9% after recrystallization. The enantiomeric excess was greater than 99.0%.

Novel derivatives of substituted 6-fluorobenzothiazole diamides: synthesis, antifungal activity and cytotoxicity

A new series of 1-[(1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]-3-substituted phenyl diamides were synthesized in vitro as potential antifungal agents. Chemical structures of the synthesised compounds were substantiated by IR, 1H, 13C, 19F nuclear magnetic resonance spectra, high resolution mass spectrometry, elemental analysis and also by X-ray diffraction. In addition, the cytotoxicity of the most active compounds was investigated against cancer cell line (Jurkat) and one type of normal lung fibroblast cells (MRC-5) by (2,3-bis-(2-methoxy-4-nitro-5-sulfophenyl)-2H-tetrazolium-5-carboxanilide) tetrazolium salt reduction assay, propidium iodide flow cytometry assay and xCELLigence system allowing a label-free assessment of the cells proliferation. Compounds indicated as 11e, 11g, 11j, 11n and 11o, were the best of the series, showing minimum inhibitory concentration values of 6.25–50 μg/mL against pathogenic strains Candida albicans HE 169, Candida tropicalis 31/HK and Candida parapsilosis p69. Moreover compounds 11e, 11g, 11j and 11o did not show any cytotoxic effect against human Jurkat and MRC-5 cells.

Synthesis, structural characterization, antimicrobial and antifungal activity of substituted 6-fluorobenzo[d]thiazole amides

A series of novel 1-[(1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]-3-substituted phenyl amides was synthesized by the condensation reaction of (1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethanamine with substituted benzoyl chlorides under mild conditions. Their structures were confirmed by 1H NMR, 13C NMR and 19F NMR spectra, elemental analyses and in three cases also by single-crystal X-ray diffraction techniques. The optical activities were confirmed by optical rotation measurements. All the synthesized compounds were screened for antibacterial and antifungal activity against a variety of bacterial and fungal strains. Some of the compounds reveal antibacterial and antifungal activity comparable or slightly better to that of chloramphenicol, cefoperazone and amphotericin B used as medicinal standards.

Synthesis of 1-[(1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]-3-substituted phenyl ureas and their inhibition activity to acetylcholinesterase and butyrylcholinesterase

A series of novel 1-[(1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]-3- substituted phenyl ureas were synthesized by the condensation of (1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethanamine with substituted phenyl isocyanates under mild conditions. Their structures were confirmed 1H, 13C, and 19F NMR spectra, and elemental analyses. The optical activities were confirmed by optical rotation measurements. The inhibition activity of 1-[(1R)-1-(6-fluoro-1,3-benzothiazol-2- yl)ethyl]-3-substituted phenyl ureas to acetylcholinesterase (ACHE) and butyrylcholinesterase (BCHE) was also tested. Preliminary bioassay indicated that the target ureas displayed excellent acetylcholinesterase and butyrylcholinesterase inhibition activity.

AN IMPROVED PROCESS FOR PREPARATION OF ALANINE-NCA

Alanine-N-carboxy anhydride (Tyrosine-NCA, I) is one of the four amino acid building blocks used in the preparation of glatiramer acetate. The present invention describes a process for preparation of alanine-NCA by industrially convenient, environmentally friendly and safe process involving the reaction of triphosgene and tyrosine. Alanine-NCA obtained by this process is > 99.0% pure with 0.01% chloride content and substantially free from tyrosine impurity.

A new simple and quantitative synthesis of α-aminoacid-N-carboxyanhydrides (oxazolidines-2,5-dione)

Nitrosation of chiral N-carbamoylaminoacids with a mixture of NO and O2 gives, with the same configuration and in quantitative yield the corresponding α-aminoacid-N-carboxyanhydrides (NCA), well known precursors of peptides. The by products of this reaction are N2 and H2O. Copyright (C) 1996 Elsevier Science Ltd.

THE PREPARATION OF N-CARBOXYANHYDRIDES OF α-AMINO ACIDS USING BIS(TRICHLOROMETHYL)CARBONATE

A syntheis of the N-carboxyanhydrides (NCA's) of several α-amino acids using bis(trichloromethyl)carbonate, 1, is reported.The triphosgene is used to supply phosgene in situ in stoichiometric amounts; it is particularly effective for preparing NCA's of amino acids with long, aliphatic side chains.

ENANTIOMERIC QUANTIFICATIONS OF AMINO ACIDS THROUGH THEIR Nα-ACYL AMIDES BY GAS CHROMATOGRAPHY.

Apparent separation of 1.1 or higher on Chiralsil Val III can be obtained for Nα-acyl N-alkyl aminoacid amides allowing the use of short capillary gas chromatographic columns.A clean derivatization protocol without racemization is described, proceding through the NCA derivatives that are prepared from "in situ" silylated amino acids with trimethylsilyl cyanide.

SYNTHETIC ENZYMES-4. HIGHLY ENANTIOSELECTIVE EPOXIDATION BY MEANS OF POLYAMINOACIDS IN A TRIPHASE SYSTEM: INFLUENCE OF STRUCTURAL VARIATIONS WITHIN THE CATALYSTS.

The asymmetric epoxidation of chalcone and other electron-poor olefins in a triphase system (water-organic solvent-polyaminoacid) affords optically active oxiranes.The influence of the molecular structure of catalysts and of their secondary conformation on the enantioselectivity of the reaction has also been examined.