4658-69-9

Upstream product

• 4658-67-7 Methyl-phenyl-brenztraubensaeureamid 
• 201230-82-2 carbon monoxide 
• 672-65-1 (1-chloroethyl)benzene 
• 585-71-7 (1-bromoethyl)benzne 
• 116130-11-1 (+/-)-(Z)-9-methylchorismic acid 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 74-88-4 methyl iodide 
• 22122-01-6 2-Aethoxy-3-methyl-zimtsaeure-aethylester 
• 5801-57-0 (Z)-2-hydroxy-3-phenyl-acrylic acid 
• 24441-66-5 2-carbonyl-3-phenylbutyric acid ethyl ester 
• 63-68-3 L-methionine 
• 114-76-1 sodium phenylphyruvate 
• 92288-80-7 2-carbamoyl-3-methyl-3-phenyl-oxiranecarboxylic acid 
• 186432-13-3 methyl 2-amino-4-phenylbutanoate 

Downstream Products

• 2643-78-9 (S)-2-amino-3(RS)-methyl-3-phenylpropioic acid 
• 91133-59-4 3-methyl-3-phenyl-2-oxobutanoic acid 
• 676627-53-5 3-methyl-3-(4-bromophenyl)-2-oxobutanoic acid 
• 676627-55-7 4-bromo-N,β,β-trimethylphenylalanine 
• 676627-57-9 4-bromo-N-β,β-trimethylphenylalanyl-N¹-[(1S,2E)-4-ethoxy-1-isopropyl-3-methyl-4-oxo-2-butenyl]-N¹,3-dimethyl-valinamide 
• 145432-51-5 (βR)-N-(tert-butoxycarbonyl)-β-methyl-L-phenylalanine 
• 25488-27-1 threo-L-(2S,3R)-β-methylphenylalanine 

Relevant academic research and scientific papers

N-(HETEROCYCLYL AND HETEROCYCLYLALKYL)-3-BENZYLPYRIDIN-2-AMINE DERIVATIVES AS SSTR4 AGONISTS

Disclosed are compounds of Formula (1), and pharmaceutically acceptable salts thereof, wherein n, R1, R4, R5, R6, R7, R8, R9, R10, R11, R14, Xsu

Stereoselective Synthesis of β-Branched Aromatic α-Amino Acids by Biocatalytic Dynamic Kinetic Resolution**

β-Branched noncanonical amino acids are valuable molecules in modern drug development efforts. However, they are still challenging to prepare due to the need to set multiple stereocenters in a stereoselective fashion, and contemporary methods for the synthesis of such compounds often rely on the use of rare-transition-metal catalysts with designer ligands. Herein, we report a highly diastereo- and enantioselective biocatalytic transamination method to prepare a broad range of aromatic β-branched α-amino acids. Mechanistic studies show that the transformation proceeds through dynamic kinetic resolution that is unique to the optimal enzyme. To highlight its utility and practicality, the biocatalytic reaction was applied to the synthesis of several sp3-rich cyclic fragments and the first total synthesis of jomthonic acid A.

Tricyclic derivative inhibitor as well as preparation method and applications thereof

The invention relates to a tricyclic derivative inhibitor as well as a preparation method and applications thereof, in particular to a compound shown in a general formula (I) in the description, a preparation method of the compound, pharmaceutical composi

Formation of Complex α-Imino Esters via Multihetero-Cope Rearrangement of α-Keto Ester Derived Nitrones

A sequential benzoylation and multihetero-Cope rearrangement of α-keto ester derived nitrones has been developed. The reaction furnishes a diverse array of complex α-imino ester derivatives. The products can be transformed into amino alcohols via LiAlH 4 reduction.

Asymmetric C-Alkylation by the S-Adenosylmethionine-Dependent Methyltransferase SgvM

S-Adenosylmethionine-dependent methyltransferases (MTs) play a decisive role in the biosynthesis of natural products and in epigenetic processes. MTs catalyze the methylation of heteroatoms and even of carbon atoms, which, in many cases, is a challenging reaction in conventional synthesis. However, C-MTs are often highly substrate-specific. Herein, we show that SgvM from Streptomyces griseoviridis features an extended substrate scope with respect to the nucleophile as well as the electrophile. Aside from its physiological substrate 4-methyl-2-oxovalerate, SgvM catalyzes the (di)methylation of pyruvate, 2-oxobutyrate, 2-oxovalerate, and phenylpyruvate at the β-carbon atom. Chiral-phase HPLC analysis revealed that the methylation of 2-oxovalerate occurs with R selectivity while the ethylation of 2-oxobutyrate with S-adenosylethionine results in the S enantiomer of 3-methyl-2-oxovalerate. Thus SgvM could be a valuable tool for asymmetric biocatalytic C-alkylation reactions.

Probing the interaction of HTI-286 with tubulin using a stilbene analogue

HTI-286 is a synthetic analogue of the natural product hemiasterlin. HTI-286 is a potent antitumor agent that induces tubulin oligomerization. To investigate the binding stoichiometry and the binding site during this ligand-induced tubulin association, we

Enamine/imine tautomerism in α,β-unsaturated-α-amino acids

Investigation of the α,β-unsaturated-α-amino acids-dehydrovaline, dehydrophenylalanine, and dehydropipecolinic acid-revealed that these compounds undergo rapid hydrolysis in neutral aqueous medium, via the imine tautomers, even when the corresponding este

Reactions of Trialkylsilyl Trifluoromethanesulfonates XI. - Synthesis of α-Oxocarboxylic Acid Derivatives from 2-O-Functionalized Trimethylsilyl Ketene Acetals

The cyclic ketene acetals 3, 5 are prepared from the dioxolanone 2 resp. the oxazolidinediones 4 by silylation with trimethylsilyl triflate (1)/triethylamine.In an aldol addition/Peterson olefination reaction catalysed by 1 the ketene acetals 3, 5 yield the (E/Z)-benzylidene derivatives 7, 12, 13 in reaction with aromatic aldehydes 6.In a side reaction the α-(trimethylsilyl)benzylidene derivatives 8 are formed from 3 and 6.Compounds 7 can be hydrolysed to yield α-ketocarboxylic acids 14.The latter are also obtained via β-elimination of trimethylsilanol from 2,3-bis(trimethylsiloxy)carboxylic acid anhydride/DMAP/pyridine. Key Words: 1,3-Dioxolanes / 1,3-Oxazolidines / α-Oxocarboxylic acids

Uncatalyzed and Chorismate Mutase Catalyzed Claisen Rearrangement of (Z)-9-Methylchorismic Acid

A synthesis of (-)- and (+/-)-(Z)-9-methylchorismic acid (3) is reported.The half-life for the uncatalyzed Claisen rearrangement of (+/-)-3 in H2O (pH 7.5, 30 deg C) is 5.7 h.Chorismate analogue (-)-3 was a modest substrate for chorismate mutase (chorismate mutase-prephenate dehydrogenase from E. coli): Km = 4.0 mM, kcat./kuncat. = 4.2*104.It was established that the enzyme-catalyzed Claisen rearrangement of (-)-3 proceeds through a chairlike transition state in similar fashion to the chorismate mutase catalyzed rearrangement of (-)-chorismic acid (1).

COBALT-CATALYZED LOW PRESSURE DOUBLE CARBONYLATION OF ARYL AND SECONDARY BENZYL HALIDES

α-Ketoacids can be easily synthesized with satisfactory yields and selectivities by carbonylation of aryl halides and secondary benzyl halides under very mild conditions.The reactions are catalyzed by Co2(CO)8 in alcoholic solvents; the presence of a methyl source (dimethyl sulfate or methyl iodide) is necessary for the carbonylation of the aryl halides.Base, temperature and solvent have large effects on the course of the reaction.