100665-68-7

Upstream product

• 74-96-4 ethyl bromide 
• 114155-71-4 N-benzylidenephenylalanine tert-butyl ester 
• 129893-52-3 3-Benzyl-5H,10bH-oxazolo<3,2-c><1,3>benzoxazine-2(3H),5-dione 
• 164262-30-0 ethyl 2-amino-2-ethyl-3-phenylpropionate 
• 129786-62-5 (3S,9bR)-3-Benzyl-3-ethyl-9bH-1,5-dioxa-3a-aza-cyclopenta[a]naphthalene-2,4-dione 

Downstream Products

• 169611-21-6 Ac-(Aib)2-L-(αEt)Phe-(Aib)2-OBu^t 
• 169611-18-1 Z-L-(αEt)Ph-(Aib)2-OBu^t 
• 169611-15-8 Z-L-(αEt)Phe-Aib-OBu^t 
• 169611-27-2 H-L-(αEt)Phe-(Aib)2-OBu^t 
• 1026308-57-5 (S)-4-Benzyl-2-benzyloxy-4-ethyl-4H-oxazol-5-one 
• 1028284-40-3 (S)-4-Benzyl-2-(4-bromo-phenyl)-4-ethyl-4H-oxazol-5-one 
• 169611-04-5 Z-L-(αEt)Phe-OH 

Relevant academic research and scientific papers

Enzymatic resolution of α,α-disubstituted α-amino acid esters and amides

The scope and limitations of the enzymatic resolution of α,α-disubstituted α-amino acid amides by an amino acid amidase from Mycobacterium neoaurum and of the corresponding ethyl esters with Pig liver esterase (PLE) have been studied. Moderate enantiomeric excesses were obtained with PLE, with only a narrow substrate specificity. Mycobacterium neoaurum on the contrary yields a broad range of S-α,α-disubstituted α-amino acids 1 and the corresponding R-amides 2.

METHOD FOR PRODUCING AMINO ACID AND AMINO ACID SYNTHESIS KIT

PROBLEM TO BE SOLVED: To provide a method for producing an amino acid and an amino acid synthesis kit, which enable synthesis of a desired amino acid in high stereoselectivity efficiently and in a very short time, irrespective whether a radioactive isotope is contained or not. SOLUTION: A method for producing an amino acid and an amino acid synthesis kit are disclosed. The method for producing an amino acid of the present invention comprises a step of alkylating a substrate compound with an alkylating agent in the presence of an optically active phase transfer catalyst as well as a medium and an inorganic base. An amount of use of the optically active phase transfer catalyst is 1 equivalent or more and 1000 equivalents or less relative to the alkylating agent. According to the present invention, a desired amino acid and a derivative thereof can be produced in high stereoselectivity efficiently and in a very short time. Therefore, the present production method is useful, for example, for research and development, and production of a radioactively labelled amino acid and a derivative thereof, which can be used as a tracer for neurodegenerative diseases such as Parkinson disease and Alzheimer disease, heart diseases, and cancerous diseases. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

A synthesis of optically active α-quaternary α-amino acids and esters by assembling three components, ketones, (R)-chloromethyl p-tolyl sulfoxide, and sodium azide, via sulfinyloxiranes

Treatment of lithium α-sulfinyl carbanion of chloromethyl p-tolyl sulfoxides with ketones at low temperature afforded adducts in almost quantitative yields, which were exposed to t-BuOK to give sulfinyloxiranes in high yields. The sulfinyloxirane was reac

Chemo-Enzymic Synthesis of Optically Active α,α-Disubstituted α-Amino Acids

A series of α,α-disubstituted α-amino esters was chemically synthesized and then resolved through enantioselective hydrolysis catalysed by a new enzyme isolated from crude Humicola langinosa lipase.This enzyme only accepts free amino esters as substrates with neither lipase activity toward olive oil nor esterase activity toward o-nitrophenyl butyrate.It is unique in that it successfully catalyses the resolution of amino esters with two large α-alkyl groups including aliphatic, aromatic and cyclic amino esters.Examples of resolutions where the alkyl groups differ in size by as little as a single carbon atom have been demonstrated.For determination of absolute configuration, some of the optically active α,α-disubstituted amino acids were also prepared through Schoellkopf's asymmetric synthesis and the structures were verified by X-ray crystallography.A model depicting the substrate binding site of the enzyme is proposed.

Process for the preparation of alpha-alkylated alpha-amino acids and alpha-halogenated alpha-amino acids

A novel process for the preparation of α-alkylated α-amino acids and α-halogenated α-amino acids is disclosed. These α-alkylated α-amino acids and α-halogenated α-amino acids are useful as intermediates for the preparation of enzyme inhibitors (for example, renin inhibitors) and other peptides or amino acid derivatives or analogs.

Synthesis of Optically Pure α-Alkylated α-Amino Acids and a Single-Step Method for Enatiomeric Excess Determination

A method for the enzymatic resolution of the amides of some racemic α-alkylated amino acids is described as well as a method involving derivatization with (S)-2-chloropropionyl chloride followed by 1H NMR analysis to establish the enantiomeric excesses of the free amino acids.