METHOD FOR PRODUCING AMINO ACID AND AMINO ACID SYNTHESIS KIT

Title:

METHOD FOR PRODUCING AMINO ACID AND AMINO ACID SYNTHESIS KIT

Document Type and Number:

WIPO Patent Application WO/2014/126244

Kind Code:

A1

Abstract:

Disclosed are a method for producing an amino acid and an amino acid synthesis kit that can efficiently and in an extremely short period of time synthesize a desired amino acid at a high stereoselectivity regardless of the presence/absence of a radioisotope. The method for producing an amino acid includes a step for alkylating a compound that is the substrate by means of an alkylating agent in the presence of an optically active phase-transfer catalyst and a base that is inorganic and in a medium, and the amount of the optically active phase-transfer catalyst used is a proportion of 1-1000 equivalents inclusive with respect to the alkylating agent. By means of the present invention, it is possible to produce a desired amino acid and a derivative thereof at a high stereoselectivity, efficiently, and in an extremely short period of time. As a result, the present invention is useful in the production and research and development of a radiolabelled amino acid and a derivative thereof usable as a tracer for example for neurodegenerative diseases such as Parkinson's disease and Alzheimer's disease, cardiovascular diseases, and cancer.

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Inventors:

YAMAMOTO KENICHIRO (JP)
KODAMA KAZUYA (JP)
ANZAI KINSEI (JP)
MATSUYAMA KEISUKE (JP)
SASANO YUMI (JP)
HASHIZUME YOSHINOBU (JP)
HUME WILLIAM EWAN (JP)
YASHIO KEIJI (JP)
NOZAKI SATOSHI (JP)

Application Number:

PCT/JP2014/053659

Publication Date:

August 21, 2014

Filing Date:

February 17, 2014

Export Citation:

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Assignee:

NAGASE & CO LTD (JP)
RIKEN (JP)

International Classes:

C07C227/18; C07B53/00; C07C229/08; C07C229/34

Domestic Patent References:

WO2005073196A1

2005-08-11

Foreign References:

JP2008179566A	2008-08-07
JP2001048866A	2001-02-20
JP2008007460A	2008-01-17
JP2008007461A	2008-01-17
JP2005041791A	2005-02-17

Other References:

OOI, T. ET AL.: "Design of N-Spiro C2-Symmetric Chiral Quaternary Ammonium Bromides as Novel Chiral Phase-Transfer Catalysts:Synthesis and Application to Practical Asymmetric Synthesis of alpha-Amino Acids", J. AM. CHEM. SOC., vol. 125, no. 17, 2003, pages 5139 - 5151
OOI, T. ET AL.: "Molecular Design of a C2- Symmetric Chiral Phase-Transfer Catalyst for Practical Asymmetric Synthesis of a-Amino Acids", J. AM. CHEM. SOC., vol. 121, no. 27, 1999, pages 6519 - 6520
OOI, T. ET AL.: "Practical Catalytic Enantioselective Synthesis of sigma, sigma-Dialkyl-sigma- amino Acids by Chiral Phase-Transfer Catalysis", J. AM. CHEM. SOC., vol. 122, 2000, pages 5228 - 5229
KITAMURA, M. ET AL.: "Powerful Chiral Phase- Transfer Catalysts for the Asymmetric Synthesis of a-Alkyl- and alpha,alpha-Dialkyl-alpha-amino Acids", ANGEW. CHEM. INT. ED., vol. 44, 2005, pages 1549 - 1551
KITAMURA, MASANORI ET AL.: "Combinatorial design of simplified high-performance chiral phase- transfer catalysts for practical asymmetric synthesis of a-alkyl- and alpha,alpha-dialkyl-alpha-amino acids", CHEMISTRY - AN ASIAN JOURNAL, vol. 3, no. 8-9, 2008, pages 1702 - 1714