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    Enzymatic coupling reaction of N-protected-L-aspartic acid and phenylalanine methyl ester
    1.
    发明授权
    Enzymatic coupling reaction of N-protected-L-aspartic acid and phenylalanine methyl ester 失效
    N-保护的L-天冬氨酸和苯丙氨酸甲酯的酶偶联反应

    公开(公告)号：US5693485A

    公开(公告)日：1997-12-02

    申请号：US729507

    申请日：1996-10-11

    申请人： Tsuneo Harada ,  Shigeaki Irino ,  Yukio Kunisawa ,  Kiyotaka Oyama

    发明人： Tsuneo Harada ,  Shigeaki Irino ,  Yukio Kunisawa ,  Kiyotaka Oyama

    IPC分类号： C12P13/04 ,  C07K5/072 ,  C12P21/02 ,  C12P21/00 ,  C07K5/06

    CPC分类号： C07K5/0613 ,  C12P21/02

    摘要： The invention relates to a process for the preparation of N-protected-L-aspartyl-L-phenylalanine methyl ester by enzymatic coupling of an N-protected-L-aspartic acid and L- or DL-phenylalanine methyl ester in an aqueous solution with formation of a precipitate using a thermolysin-like protease enzyme, wherein a water-immiscible organic solvent is added to and blended with the reaction system during the formation of the precipitate in the course of the coupling reaction, which organic solvent has a relatively high affinity for the precipitate. The process is particularly suitable as a continuous process. The method results in lower enzyme deactivation during and after the enzymatic coupling reaction and in larger and thicker precipitated crystals.

    摘要翻译： 本发明涉及通过N-保护的L-天冬氨酸和L-或DL-苯丙氨酸甲酯在水溶液中的酶偶联来制备N-保护的L-天冬氨酰基-L-苯丙氨酸甲酯的方法， 使用嗜热菌蛋白酶蛋白酶形成沉淀物，其中在偶联反应过程中在形成沉淀物期间向反应体系中加入与水不混溶的有机溶剂并与其混合，该有机溶剂具有较高的亲和力 为沉淀。 该方法特别适合作为连续方法。 该方法在酶偶联反应期间和之后以及较大和较厚的沉淀晶体中导致较低的酶失活。

    Method for reductive elimination of protecting groups
    4.
    发明授权
    Method for reductive elimination of protecting groups 失效
    还原消除保护基团的方法

    公开(公告)号：US4564471A

    公开(公告)日：1986-01-14

    申请号：US188107

    申请日：1980-09-17

    申请人： Katsumi Sugiyama ,  Hideo Takeda ,  Hiroko Sato ,  Yuji Nonaka ,  Kiyotaka Oyama ,  Masashige Kubo

    发明人： Katsumi Sugiyama ,  Hideo Takeda ,  Hiroko Sato ,  Yuji Nonaka ,  Kiyotaka Oyama ,  Masashige Kubo

    IPC分类号： C07B31/00 ,  C07B51/00 ,  C07C67/00 ,  C07C227/00 ,  C07C227/16 ,  C07C227/18 ,  C07C227/20 ,  C07C231/00 ,  C07K1/06 ,  C07K1/12 ,  C07K5/075 ,  C07C101/02

    CPC分类号： C07K1/12 ,  C07K5/0613 ,  Y02P20/55

    摘要： The invention provides a novel and efficient method for the elimination of protecting groups, e.g. benzyloxycarbonyl group, from a protected amino acid, peptide or derivative thereof having at least one functional group protected by a protecting group, e.g. a lower alkyl ester of N-benzyloxycarbonyl-.alpha.-L-aspartyl-L-phenylalanine by catalytic hydrogen reduction to produce free amino acid, peptide or derivative thereof. In contrast to the conventional procedures in which the reaction is carried out in a solvent dissolving both the starting compound and the product compound or a solvent dissolving the starting compound but not dissolving the product compound, the inventive method utilizes a binary two-phase reaction medium composed of water and an organic solvent not freely miscible with water such as toluene. The reaction takes place in the organic phase containing the starting compound dissolved and the catalyst dispersed therein whereas the reaction product which is water-soluble is smoothly and successively transferred into the aqueous phase so that advantages are obtained in the unexpectedly high yield of the product as well as in the easiness of handling the reaction mixture after completion of the reaction.

    摘要翻译： 本发明提供了一种用于消除保护基团的新型和有效的方法，例如， 苄氧羰基，被保护的氨基酸，具有至少一个被保护基保护的官能团的肽或衍生物。 N-苄氧羰基-α-L-天冬氨酰基-L-苯丙氨酸的低级烷基酯通过催化氢还原反应产生游离氨基酸，肽或其衍生物。 与在溶解起始化合物和产物化合物的溶剂或溶解起始化合物但不溶解产物化合物的溶剂中进行反应的常规方法相反，本发明的方法利用二元二相反应介质 由水和不能与水如甲苯自由混溶的有机溶剂组成。 反应发生在含有溶解的起始化合物和分散在其中的催化剂的有机相中，而水溶性的反应产物顺利地依次转移到水相中，从而获得了产品出乎意料的高产率的优点， 以及在反应完成后容易处理反应混合物。

    Method for manufacturing dipeptides
    6.
    发明授权
    Method for manufacturing dipeptides 失效
    二肽制造方法

    公开(公告)号：US4284721A

    公开(公告)日：1981-08-18

    申请号：US136347

    申请日：1980-04-01

    申请人： Kiyotaka Oyama ,  Shigeaki Nishimura ,  Yuji Nonaka ,  Tsutomu Hashimoto ,  Keiichi Kihara

    发明人： Kiyotaka Oyama ,  Shigeaki Nishimura ,  Yuji Nonaka ,  Tsutomu Hashimoto ,  Keiichi Kihara

    IPC分类号： C12P21/02 ,  C07K5/072 ,  C07K5/075 ,  C07C103/52

    CPC分类号： C07K5/0613

    摘要： An improvement in a method for manufacturing dipeptides from an N-substituted aspartic acid and a phenylalanine lower alkyl ester. The two starting materials are allowed to react with each other in the presence of an immobilized metallo-proteinase in an organic solvent immiscible with water. The enzyme can be recovered for reuse thereof. The loss of materials due to the hydrolysis of the phenylalanine lower alkyl ester is reduced, so that use of the phenylalanine lower alkyl ester in a nearly stoichiometric quantity suffices for the reaction to ensure an improved yield and reduction in cost of industrial production.

    摘要翻译： 从N-取代天冬氨酸和苯丙氨酸低级烷基酯制备二肽的方法的改进。 允许两种起始物质在固定化的金属蛋白酶存在下在与水不混溶的有机溶剂中相互反应。 该酶可以回收再利用。 由于苯丙氨酸低级烷基酯的水解导致的材料损失减少，因此使用近乎化学计量的苯丙氨酸低级烷基酯足以使反应保证提高的产率和降低工业生产的成本。

    Process for producing DL-phenylalanine
    8.
    发明授权
    Process for producing DL-phenylalanine 失效
    生产DL-苯丙氨酸的方法

    公开(公告)号：US4704471A

    公开(公告)日：1987-11-03

    申请号：US854709

    申请日：1986-04-23

    申请人： Tuneo Harada ,  Kiyotaka Oyama

    发明人： Tuneo Harada ,  Kiyotaka Oyama

    IPC分类号： C07C67/00 ,  C07C227/00 ,  C07C227/08 ,  C07C229/36 ,  C07C99/00

    CPC分类号： C07C227/08

    摘要： A process for producing DL-phenylalanine by reacting an .alpha.-halogeno-.beta.-phenylpropionic acid represented by the general formula: ##STR1## where X is a halogen atom, or its salt, with ammonia, characterized in that the reaction is conducted while supplying the .alpha.-halogeno-.beta.-phenylpropionic acid or its salt into aqueous ammonia charged in a reactor in advance.

    摘要翻译： 通过使由以下通式表示的α-卤代-β-苯基丙酸（其中X是卤素原子）或其盐与氨反应生成DL-苯丙氨酸的方法，其特征在于反应是 在将α-卤代-β-苯基丙酸或其盐预先提供在反应器中的氨水中进行。

    Addition compound of dipeptide derivative and amino acid derivative
    10.
    发明授权
    Addition compound of dipeptide derivative and amino acid derivative 失效
    二肽衍生物和氨基酸衍生物的加成化合物

    公开(公告)号：US4436925A

    公开(公告)日：1984-03-13

    申请号：US270025

    申请日：1982-06-03

    申请人： Yoshikazu Isowa ,  Muneki Ohmori ,  Kaoru Mori ,  Tetsuya Ichikawa ,  Yuji Nonaka ,  Keiichi Kihara ,  Kiyotaka Oyama ,  Heijiro Satoh ,  Shigeaki Nishimura

    发明人： Yoshikazu Isowa ,  Muneki Ohmori ,  Kaoru Mori ,  Tetsuya Ichikawa ,  Yuji Nonaka ,  Keiichi Kihara ,  Kiyotaka Oyama ,  Heijiro Satoh ,  Shigeaki Nishimura

    IPC分类号： C07K5/072 ,  C07K5/075 ,  C07C101/00

    CPC分类号： C07K5/0613

    摘要： Addition compounds have the formula ##STR1## wherein R.sub.1 represents an aliphatic oxycarbonyl group, benzyloxycarbonyl group which can have nuclear substituents or benzoyl, aromatic sulfonyl or aromatic sulfinyl group; R.sub.2 represents methyl, isopropyl, isobutyl, isoamyl or benzyl group; R.sub.3 represents a lower alkoxyl, benzyloxy or benzhydryloxy group and n represents 1 or 2.The addition compounds are produced by reacting an N-substituted monoaminodicarboxylic acid having the formula ##STR2## with an amino carboxlic acid ester having the formula in an aqueous medium in the presence of a protease and reacting the resulting dipeptide ester with the amino carboxylic acid ester and separating the addition compound.The addition compounds can be decomposed into the constituent dipeptide esters and amino acid esters by the action of an acid.

    摘要翻译： 加成化合物具有式（I）其中R 1表示脂族氧羰基，可具有核取代基的苄氧基羰基或苯甲酰基，芳族磺酰基或芳族亚磺酰基; R 2表示甲基，异丙基，异丁基，异戊基或苄基; R3表示低级烷氧基，苄氧基或二苯甲氧基，n表示1或2.加成化合物通过使具有式（IV）的式（I）所示的N-取代的单氨基二羧酸与式 （V）在水性介质中，在蛋白酶存在下，使得到的二肽酯与氨基羧酸酯反应并分离加成化合物。 加成化合物可以通过酸的作用分解成组分二肽酯和氨基酸酯。