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    METHOD FOR PRODUCING a-SUBSTITUTED CYSTEINE OR SALT THEREOF OR SYNTHETIC INTERMEDIATE OF a-SUBSTITUTED CYSTEINE
    1.
    发明申请
    METHOD FOR PRODUCING a-SUBSTITUTED CYSTEINE OR SALT THEREOF OR SYNTHETIC INTERMEDIATE OF a-SUBSTITUTED CYSTEINE 审中-公开
    生产取代的CYSTEINE或其盐的方法或其取代的CYSTEINE的合成中间体

    公开(公告)号：US20160083341A1

    公开(公告)日：2016-03-24

    申请号：US14888576

    申请日：2014-05-01

    申请人： API Corporation

    发明人： Yuuki Asuma ,  Hisatoshi Uehara ,  Tomoko Maeda ,  Yasuyo Saito ,  Ryoma Miyake ,  Hiroshi Kawabata

    IPC分类号： C07C319/06 ,  C07C323/52 ,  C12P13/12 ,  C07C323/58 ,  C07D277/14 ,  C07C319/14 ,  C07C319/20 ,  C07C323/60

    CPC分类号： C07C319/06 ,  C07C319/02 ,  C07C319/14 ,  C07C319/20 ,  C07C323/52 ,  C07C323/58 ,  C07C323/60 ,  C07D277/14 ,  C12P13/12 ,  C07C323/12 ,  C07C323/03

    摘要： According to the present invention, it becomes possible to perform a process for converting into an α-substituted cysteine represented by general formula (1) or a salt thereof at low cost and on an industrial scale by employing a process that is routed through a compound represented by general formula (3) to a compound represented by general formula (6). Particularly, by employing a process that is routed through a compound represented by general formula (7-2), it becomes possible to detach a tert-butyl protection group in a simple manner and to produce the compound represented by general formula (1) with high purity. Furthermore, by employing a process that is routed through tert-butylthiomethanol or a process that is routed through a compound represented by general formula (9), it becomes possible to produce a compound represented by general formula (2) without generating bischloromethylether that is an oncogenic substance. In the production of an α-substituted-D-cysteine or a salt thereof, it becomes possible to perform a process for converting the compound represented by general formula (2) into a compound represented by general formula (3S) in one step by allowing an enzyme or the like to act on the compound represented by general formula (2).

    摘要翻译： 根据本发明，可以通过使用通过化合物的方法，以低成本和工业规模进行转化成由通式（1）表示的α-取代的半胱氨酸或其盐的方法 由通式（3）表示的化合物与通式（6）表示的化合物反应。 特别是通过使用通过通式（7-2）表示的化合物的方法，可以简单地分离叔丁基保护基，并制备通式（1）表示的化合物与 高纯度 此外，通过使用通过叔丁基硫醇的方法或通过通式（9）表示的化合物的方法，可以生成由通式（2）表示的化合物，而不产生作为 致癌物质。 在制备α-取代-D-半胱氨酸或其盐时，可以通过以下步骤进行将由通式（2）表示的化合物转化为通式（3S）表示的化合物的方法：允许 酶等作用于由通式（2）表示的化合物。

    Pipecolinic acid 4-hydroxylase and method for producing 4-hydroxy amino acid using same
    4.
    发明授权
    Pipecolinic acid 4-hydroxylase and method for producing 4-hydroxy amino acid using same 有权

    公开(公告)号：US09969988B2

    公开(公告)日：2018-05-15

    申请号：US15115028

    申请日：2015-01-27

    申请人： API CORPORATION

    发明人： Makoto Hibi ,  Jun Ogawa ,  Ryoma Miyake ,  Hiroshi Kawabata

    IPC分类号： C12P13/04 ,  C12P17/10 ,  C12P17/12 ,  C12N9/02

    CPC分类号： C12N9/0071 ,  C12P13/04 ,  C12P17/10 ,  C12P17/12 ,  C12Y114/00 ,  C12Y114/11006

    摘要： The present invention provides a pipecolic acid 4-hydroxylase protein exemplified by the following (A), (B), and (C), having activity to react with L-pipecolic acid in the presence of 2-oxoglutaric acid and iron(II) ions to produce trans-4-hydroxy-L-pipecolic acid, and a method for producing 4-hydroxy amino acid, which method comprises reacting the pipecolic acid 4-hydroxylase protein, cells containing the protein, a treated product of the cells, and/or a culture liquid obtained by culturing the cells, with α-amino acid to produce 4-hydroxy amino acid: (A) a polypeptide comprising the amino acid sequence represented by SEQ ID NO:2, 4, 6, 8, 10, 12, 16, or 18; (B) a polypeptide comprising the amino acid sequence represented by SEQ ID NO:2, 4, 6, 8, 10, 12, 16, or 18 except that one or several amino acids are deleted, substituted, and/or added, and having pipecolic acid 4-hydroxylase activity; and (C) a polypeptide having an amino acid sequence that is not less than 80% identical to the amino acid sequence represented by SEQ ID NO:2, 4, 6, 8, 10, 12, 16, or 18, and having pipecolic acid 4-hydroxylase activity.

    Hydrolase protein
    5.
    发明授权
    Hydrolase protein 有权
    水解酶蛋白

    公开(公告)号：US09334509B2

    公开(公告)日：2016-05-10

    申请号：US14637429

    申请日：2015-03-04

    申请人： API CORPORATION

    发明人： Hiroshi Kawabata ,  Ryoma Miyake ,  Kuniko Asada ,  Ryouhei Katou

    IPC分类号： C12P7/62 ,  C12N9/18 ,  C12P41/00 ,  C12N9/14

    CPC分类号： C12P7/62 ,  C12N9/14 ,  C12N9/18 ,  C12P41/005 ,  Y02P20/52

    摘要： It is an object of the present invention to provide a novel hydrolase, which is used when dialkyl 2-vinylcyclopropane-1,1-dicarboxylate is hydrolyzed with an enzyme, so as to efficiently obtain (1S,2S)-1-alkoxycarbonyl-2-vinylcyclopropanecarboxylic acid that is useful as an intermediate for synthesizing therapeutic agents for hepatitis C. According to the present invention, there is provided a hydrolase protein, which consists of the amino acid sequence shown in any one of SEQ ID NOS. 2 to 5 and which has activity of catalyzing, at higher selectivity than the protein consisting of the amino acid sequence shown in SEQ ID NO. 1, a reaction of producing (1S,2S)-1-ethoxycarbonyl-2-vinylcyclopropanecarboxylic acid from diethyl 2-vinylcyclopropane-1,1 -dicarboxylate.

    摘要翻译： 本发明的一个目的是提供一种新的水解酶，其在2-乙烯基环丙烷-1,1-二羧酸二烷基酯用酶水解时使用，以有效地获得（1S，2S）-1-烷氧基羰基-2 - 乙烯基环丙烷羧酸，其可用作合成丙型肝炎治疗剂的中间体。根据本发明，提供了水解酶蛋白质，其由SEQ ID NOS中任一项所示的氨基酸序列组成。 2至5，并且其具有以比由SEQ ID NO。所示的氨基酸序列组成的蛋白质更高的选择性催化的活性。 1，从2-乙烯基环丙烷-1,1-二羧酸二乙酯生产（1S，2S）-1-乙氧基羰基-2-乙烯基环丙烷甲酸的反应。

    L-Lysine Hydroxylase and Production Method for Hydroxy-L-Lysine and Hydroxy-L-Pipecolic Acid Using Same
    6.
    发明申请
    L-Lysine Hydroxylase and Production Method for Hydroxy-L-Lysine and Hydroxy-L-Pipecolic Acid Using Same 有权
    L-赖氨酸羟化酶及使用其的羟基-L-赖氨酸和羟基-L-胆酸的制备方法

    公开(公告)号：US20150259715A1

    公开(公告)日：2015-09-17

    申请号：US14431193

    申请日：2014-02-18

    申请人： API CORPORATION

    发明人： Kuniki Kino ,  Ryotaro Hara ,  Ryoma Miyake ,  Hiroshi Kawabata

    IPC分类号： C12P13/08 ,  C12N9/02 ,  C12P17/12

    CPC分类号： C12P13/08 ,  C12N9/0071 ,  C12P13/04 ,  C12P17/12 ,  C12Y114/11 ,  C12Y114/11004 ,  Y02P20/52

    摘要： The present invention aims to provide a method for efficiently producing hydroxy-L-lysine. The present invention provides a method for producing hydroxy-L-lysine, the method comprising allowing 2-oxoglutarate-dependent L-lysine hydroxylase, a cell containing 2-oxoglutarate-dependent L-lysine hydroxylase, a processed product of the cell, and/or a culture broth obtained by culturing the cell, to act on L-lysine to produce hydroxy-L-lysine represented by the following General Formula (I) (wherein each of R1, R2 and R3 represents a hydrogen atom or hydroxyl group, with the proviso that at least one of R1, R2 and R3 represents a hydroxyl group).

    摘要翻译： 本发明的目的在于提供一种高效生产羟基-L-赖氨酸的方法。 本发明提供一种生产羟基-L-赖氨酸的方法，该方法包括使2-氧戊二酸依赖性L-赖氨酸羟化酶，含有2-氧戊二酸依赖性L-赖氨酸羟化酶的细胞，细胞的加工产物和/ 或通过培养细胞获得的培养液，作用于L-赖氨酸以产生由以下通式（I）表示的羟基-L-赖氨酸（其中R1，R2和R3各自表示氢原子或羟基，与 条件是R 1，R 2和R 3中的至少一个表示羟基）。

    Method for producing hydroxy-L-pipecolic acid
    8.
    发明授权
    Method for producing hydroxy-L-pipecolic acid 有权

    公开(公告)号：US10954539B2

    公开(公告)日：2021-03-23

    申请号：US15765148

    申请日：2016-09-30

    申请人： API CORPORATION

    发明人： Ryoma Miyake ,  Hiroshi Kawabata

    IPC分类号： C12P17/12 ,  C12N9/10 ,  C12N9/06 ,  C12N9/02 ,  C12N15/09

    摘要： A novel method of producing high-purity hydroxy-L-pipecolic acids in an efficient and inexpensive manner while suppressing the production of hydroxy-L-proline is provided. The method includes allowing an L-pipecolic acid hydroxylase, a microorganism or cell having the ability to produce the enzyme, a processed product of the microorganism or cell, and/or a culture liquid comprising the enzyme and obtained by culturing the microorganism or cell, to act on L-pipecolic acid as a substrate in the presence of 2-oxoglutaric acid and ferrous ion, wherein the L-pipecolic acid hydroxylase has the properties: (1) the enzyme can act on L-pipecolic acid in the presence of 2-oxoglutaric acid and ferrous ion to add a hydroxy group to the carbon atom at positions 3, 4, and/or 5 of L-pipecolic acid; and (2) the enzyme has a catalytic efficiency (kcat/Km) with L-proline that is equal to or less than 7 times the catalytic efficiency (kcat/Km) with L-pipecolic acid.

    Method for manufacturing cis-5-hydroxy-L-pipecolic acid
    9.
    发明授权
    Method for manufacturing cis-5-hydroxy-L-pipecolic acid 有权

    公开(公告)号：US10087473B2

    公开(公告)日：2018-10-02

    申请号：US15526031

    申请日：2015-11-02

    申请人： API CORPORATION

    发明人： Ryoma Miyake ,  Yasumasa Dekishima

    IPC分类号： C12N9/02 ,  C12P17/12

    摘要： A method for producing cis-5-hydroxy-L-pipecolic acid, the method comprising allowing a 2-oxoglutarate-dependent L-pipecolic acid hydroxylase to act on L-pipecolic acid to generate cis-5-hydroxy-L-pipecolic acid, wherein the 2-oxoglutarate-dependent L-pipecolic acid hydroxylase comprises the polypeptide (A), (B) or (C) below: (A) a polypeptide comprising the amino acid sequence represented by SEQ ID NO: 4 or 11; (B) a polypeptide comprising the amino acid sequence represented by SEQ ID NO: 4 or 11 except that one or several amino acids are deleted, substituted, and/or added, which polypeptide has 2-oxoglutarate-dependent L-pipecolic acid hydroxylase activity; or (C) a polypeptide comprising an amino acid sequence with an identity of not less than 60% to the amino acid sequence represented by SEQ ID NO: 4 or 11, which polypeptide has 2-oxoglutarate-dependent L-pipecolic acid hydroxylase activity.

    Method for producing hydroxy-L-pipecolic acid
    10.
    发明授权
    Method for producing hydroxy-L-pipecolic acid 有权

    公开(公告)号：US11591577B2

    公开(公告)日：2023-02-28

    申请号：US17177823

    申请日：2021-02-17

    申请人： API CORPORATION

    发明人： Ryoma Miyake ,  Hiroshi Kawabata

    IPC分类号： C12N9/02 ,  C12P17/12 ,  C12N9/10 ,  C12N9/06 ,  C12N15/09

    摘要： A novel method of producing high-purity hydroxy-L-pipecolic acids in an efficient and inexpensive manner while suppressing the production of hydroxy-L-proline is provided. The method includes allowing an L-pipecolic acid hydroxylase, a microorganism or cell having the ability to produce the enzyme, a processed product of the microorganism or cell, and/or a culture liquid comprising the enzyme and obtained by culturing the microorganism or cell, to act on L-pipecolic acid as a substrate in the presence of 2-oxoglutaric acid and ferrous ion, wherein the L-pipecolic acid hydroxylase has the properties: (1) the enzyme can act on L-pipecolic acid in the presence of 2-oxoglutaric acid and ferrous ion to add a hydroxy group to the carbon atom at positions 3, 4, and/or 5 of L-pipecolic acid; and (2) the enzyme has a catalytic efficiency (kcat/Km) with L-proline that is equal to or less than 7 times the catalytic efficiency (kcat/Km) with L-pipecolic acid.