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    Method for removing FMOC group
    3.
    发明授权
    Method for removing FMOC group 有权
    去除FMOC组的方法

    公开(公告)号：US09334302B2

    公开(公告)日：2016-05-10

    申请号：US14305841

    申请日：2014-06-16

    Applicant: Ajinomoto Co., Inc.

    Inventor： Daisuke Takahashi

    IPC: A61K38/04 ,  C07K5/00 ,  C07K7/00 ,  C07K16/00 ,  C07K17/00 ,  C07K1/00 ,  C07K1/06 ,  C07C227/16 ,  C07K1/08 ,  C07B43/04

    CPC classification number: C07K1/00 ,  C07B43/04 ,  C07C227/16 ,  C07K1/063 ,  C07K1/064 ,  C07K1/08 ,  C07C227/04 ,  C07C229/08

    Abstract: The present invention relates to a method of removing an Fmoc group, including a step of mixing a compound represented by the formula (I): HS-L-COOH  (I) wherein L is a C1-8 alkylene group optionally having substituent(s), an amino group-containing compound protected by an Fmoc group, and a base to give a reaction mixture containing a compound represented by the formula (II): Fm—S-L-COOH  (II) wherein Fm is a 9-fluorenylmethyl group, and L is as mentioned above, and an amino group-containing compound, and a step of removing the compound represented by the formula (II) by washing the obtained reaction mixture with a basic aqueous solution. According to the present invention, a removal method of Fmoc group, which can remove a dibenzofulvene derivative as a byproduct with ease, can be provided.

    Abstract translation: 本发明涉及一种除去Fmoc基团的方法，包括将式（I）表示的化合物：HS-L-COOH（I）（其中L是任选具有取代基的C 1-8亚烷基） ），由Fmoc基保护的含氨基的化合物和碱，得到含有式（II）表示的化合物的反应混合物：Fm-SL-COOH（II）其中Fm为9-芴基甲基， 和L如上所述，含氨基化合物，以及通过用碱性水溶液洗涤所得反应混合物除去由式（II）表示的化合物的步骤。 根据本发明，可以提供能够容易地除去作为副产物的二苯并菲衍生物的Fmoc基团的除去方法。

    OLIGONUCLEOTIDE PRODUCTION METHOD, AND NUCLEOSIDE, NUCLEOTIDE, OR OLIGONUCLEOTIDE
    4.
    发明申请
    OLIGONUCLEOTIDE PRODUCTION METHOD, AND NUCLEOSIDE, NUCLEOTIDE, OR OLIGONUCLEOTIDE 审中-公开

    公开(公告)号：US20180282365A1

    公开(公告)日：2018-10-04

    申请号：US16009533

    申请日：2018-06-15

    Applicant: AJINOMOTO CO., INC.

    Inventor： Kunihiro HIRAI ,  Satoshi Katayama ,  Naoko Hirose ,  Taisuke Ichimaru ,  Ken Yamashita ,  Daisuke Takahashi

    IPC: C07H21/02

    Abstract: Oligonucleotides may be produced by a process, including (1) condensing a nucleoside, nucleotide or oligonucleotide (a) or the like wherein a 5′-hydroxy group is not protected and a nucleoside, nucleotide or oligonucleotide (b) wherein a 5′-hydroxy group is protected in a non-polar solvent to give a reaction solution containing a phosphite triester product (c); (3) oxidizing or sulfurizing the phosphite triester product (c) to give a reaction solution containing an oligonucleotide (d) wherein the 5′-hydroxy group is protected; (4) deprotecting the oligonucleotide (d) to give a reaction solution containing an oligonucleotide (e) wherein the 5′-hydroxy group is not protected; and (6) adding a polar solvent to the reaction solution containing the oligonucleotide (e) and purifying the oligonucleotide (e) by solid-liquid separation or extraction.

    Oligonucleotide with protected base
    5.
    发明授权
    Oligonucleotide with protected base 有权
    具有受保护碱基的寡核苷酸

    公开(公告)号：US09371353B2

    公开(公告)日：2016-06-21

    申请号：US14491683

    申请日：2014-09-19

    Applicant: Ajinomoto Co., Inc.

    Inventor： Kunihiro Hirai ,  Satoshi Katayama ,  Takayoshi Torii ,  Ryotaro Nakaya ,  Daisuke Takahashi

    IPC: C07H1/02 ,  C07H21/00 ,  C07H1/00 ,  C07H19/06 ,  C07H19/073 ,  C07H19/173

    CPC classification number: C07H21/00 ,  C07H1/00 ,  C07H1/02 ,  C07H19/06 ,  C07H19/073 ,  C07H19/173

    Abstract: The present invention provides a protected nucleotide for elongation, which can be purified efficiently and in a high yield by a liquid-liquid extraction operation, and can achieve an oligonucleotide production method by a phosphoramidite method.It has been found that the above-mentioned problem can be solved by a particular oligonucleotide comprising a protected base and/or particular oligonucleotide protected by a branched chain-containing aromatic group at 3′-position.

    Abstract translation: 本发明提供了用于延伸的被保护的核苷酸，其可以通过液 - 液萃取操作有效地和高产率地纯化，并且可以通过亚磷酰胺方法实现寡核苷酸制备方法。 已经发现，上述问题可以通过包含受保护碱和/或在3'-位具有支链含芳族基团保护的特定寡核苷酸的特定寡核苷酸来解决。

    MORPHOLINO OLIGONUCLEOTIDE MANUFACTURING METHOD
    6.
    发明申请
    MORPHOLINO OLIGONUCLEOTIDE MANUFACTURING METHOD 有权
    莫比诺寡糖制备方法

    公开(公告)号：US20160076033A1

    公开(公告)日：2016-03-17

    申请号：US14946991

    申请日：2015-11-20

    Applicant: AJINOMOTO CO., INC.

    Inventor： Takayoshi Torii ,  Daisuke Takahashi ,  Satoshi Katayama

    IPC: C12N15/113

    CPC classification number: C12N15/113 ,  C07D413/04 ,  C07D487/04 ,  C07D519/00 ,  C07H21/00 ,  C12N15/111 ,  C12N2310/11 ,  C12N2310/3233 ,  C12N2330/30 ,  Y02P20/55

    Abstract: Using a morpholino nucleotide wherein 5′-hydroxy group or a hydroxy group present on the substituent of the 5′-hydroxy group is protected by a protecting group having an alkyl group having not less than 10 and not more than 300 carbon atoms and/or an alkenyl group having not less than 10 and not more than 300 carbon atoms as a starting material, a method capable of efficiently producing the morpholino oligonucleotide in a high yield by a liquid phase synthesis can be provided.

    Abstract translation: 使用存在于5'-羟基的取代基上的5'-羟基或羟基的吗啉代核苷酸被具有不少于10个且不多于300个碳原子的烷基的保护基保护，和/或 可以提供具有不少于10个且不超过300个碳原子的烯基作为原料，可以通过液相合成以高产率有效地制备吗啉代寡核苷酸的方法。

    Benzylic compound
    9.
    发明授权
    Benzylic compound 有权
    苄基化合物

    公开(公告)号：US09206230B2

    公开(公告)日：2015-12-08

    申请号：US14475019

    申请日：2014-09-02

    Applicant: AJINOMOTO CO., INC.

    Inventor： Daisuke Takahashi

    IPC: C07K1/06 ,  C07K5/11 ,  C07C43/23 ,  C07C217/58 ,  C07C235/40

    CPC classification number: C07K5/1019 ,  C07C43/23 ,  C07C217/58 ,  C07C235/40 ,  C07C2601/14 ,  C07K1/062

    Abstract: The present invention provides a protecting reagent that can be removed in a high yield even under acidic conditions and can afford a resulting product at a high purity in an organic synthesis reaction such as peptide synthesis and the like. The inventive protecting reagent is particular benzylic compound having only one hydroxyl group substituted by an organic group having an aliphatic hydrocarbon group having a carbon number of not less than 14.

    Abstract translation: 本发明提供即使在酸性条件下也可以以高产率除去的保护试剂，并能够在有机合成反应如肽合成等中提供高纯度的所得产物。 本发明的保护试剂是仅具有一个羟基被具有碳数不少于14的脂族烃基的有机基团取代的特定苄基化合物。

    Production method for oligonucleotides
    10.
    发明授权
    Production method for oligonucleotides 有权

    公开(公告)号：US12269841B2

    公开(公告)日：2025-04-08

    申请号：US17400488

    申请日：2021-08-12

    Applicant: AJINOMOTO CO., INC.

    Inventor： Daisuke Takahashi ,  Taisuke Ichimaru ,  Kunihiro Hirai

    IPC: C07H21/00 ,  C07H1/00

    Abstract: A method for producing an oligonucleotide, including a step of removing a temporary protecting group of a 5′-hydroxyl group by adding an acid to a protected oligonucleotide having a phosphorothioate (PS), phosphate (PO) or H-phosphonate moiety, and deacylating a by-product having an acylated 5′-hydroxyl group by solvolysis can complete a condensation reaction to improve a condensation yield, and can markedly reduce impurities such as single base deletion form (N-1mer) and the like.

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