Metabolic engineering of Escherichia coli to produce (2S, 3R, 4S)-4-hydroxyisoleucine

被引:58
|
作者
Smirnov, Sergey V. [1 ]
Kodera, Tomohiro [2 ]
Samsonova, Natalya N. [1 ]
Kotlyarova, Veronika A. [1 ]
Rushkevich, Natalya Yu [1 ]
Kivero, Alexander D. [1 ]
Sokolov, Pavel M. [1 ]
Hibi, Makoto [3 ]
Ogawa, Jun [3 ]
Shimizu, Sakayu [3 ]
机构
[1] Ajinomoto Genet Res Inst, Moscow 117545, Russia
[2] Ajinomoto Co Inc, Inst Life Sci, Kawasaki Ku, Kawasaki, Kanagawa 2108681, Japan
[3] Kyoto Univ, Div Appl Life Sci, Grad Sch Agr, Sakyo Ku, Kyoto 6068502, Japan
关键词
4-Hydroxyisoleucine; Diabetes; Dioxygenase; Biotransformation; Escherichia coli; AMINO-ACID; 4-HYDROXYISOLEUCINE; IDENTIFICATION; ALDOLASE; GENES;
D O I
10.1007/s00253-010-2772-3
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
The stereo-specific l-isoleucine-4-hydroxylase (l-isoleucine dioxygenase (IDO)) was cloned and expressed in an Escherichia coli 2 Delta strain lacking the activities of alpha-ketoglutarate dehydrogenase (EC 1.2.4.2), isocitrate liase (EC 4.1.3.1), and isocitrate dehydrogenase kinase/phosphatase (EC 2.7.11.5). The 2 Delta strain could not grow in a minimal-salt/glucose/glycerol medium due to the blockage of TCA during succinate synthesis. The IDO activity in the 2 Delta strain was able to "shunt" destroyed TCA, thereby coupling l-isoleucine hydroxylation and cell growth. Using this strain, we performed the direct biotransformation of l-isoleucine into 4-HIL with an 82% yield.
引用
收藏
页码:719 / 726
页数:8
相关论文
共 50 条
  • [1] Metabolic engineering of Escherichia coli to produce (2S, 3R, 4S)-4-hydroxyisoleucine
    Sergey V. Smirnov
    Tomohiro Kodera
    Natalya N. Samsonova
    Veronika А. Kotlyarovа
    Natalya Yu Rushkevich
    Аlexander D. Kivero
    Pavel M. Sokolov
    Makoto Hibi
    Jun Ogawa
    Sakayu Shimizu
    Applied Microbiology and Biotechnology, 2010, 88 : 719 - 726
  • [2] Engineering Bacillus subtilis Isoleucine Dioxygenase for Efficient Synthesis of (2S,3R,4S)-4-Hydroxyisoleucine
    Du, Ping
    Yan, Shuai
    Qian, Xiao-Long
    Pan, Jiang
    Zhang, Zhi-Jun
    Yu, Hui-Lei
    Xu, Jian-He
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2020, 68 (49) : 14555 - 14563
  • [3] An Organocatalyzed Enantioselective Synthesis of (2S,3R,4S)-4-Hydroxyisoleucine and Its Stereoisomers
    Kumaraswamy, Gullapalli
    Jayaprakash, Neerasa
    Sridhar, Balasubramanian
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (08): : 2745 - 2747
  • [4] Synthesis of hydantoin analogues of (2S, 3R, 4S)-4-hydroxyisoleucine with insulinotropic properties
    Sergent, Didier
    Wang, Qian
    Sasaki, N. Andre
    Ouazzani, Jamal
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (15) : 4332 - 4335
  • [5] Isolation of (2S,3R,4S)-4-Hydroxyisoleucine from Trigonella foenum graecum Seeds
    Hari, N.
    Mohan, V.
    ASIAN JOURNAL OF CHEMISTRY, 2014, 26 (10) : 3082 - 3084
  • [6] A practical synthesis of (2S,3R,4S)-4-hydroxyisoleucine, a potent insulinotropic α-amino acid from fenugreek
    Wang, Q
    Quazzani, J
    Sasaki, NA
    Potier, P
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (05) : 834 - 839
  • [7] Engineering a short-chain dehydrogenase/reductase for the stereoselective production of (2S,3R,4S)-4-hydroxyisoleucine with three asymmetric centers
    Xuan Shi
    Takuya Miyakawa
    Akira Nakamura
    Feng Hou
    Makoto Hibi
    Jun Ogawa
    Yeondae Kwon
    Masaru Tanokura
    Scientific Reports, 7
  • [8] Engineering a short-chain dehydrogenase/reductase for the stereoselective production of (2S, 3R, 4S)-4-hydroxyisoleucine with three asymmetric centers
    Shi, Xuan
    Miyakawa, Takuya
    Nakamura, Akira
    Hou, Feng
    Hibi, Makoto
    Ogawa, Jun
    Kwon, Yeondae
    Tanokura, Masaru
    SCIENTIFIC REPORTS, 2017, 7
  • [9] Multi-Step Synthesis and Biological Evaluation of Analogues of Insulin Secretagogue (2S,3R,4S)-4-Hydroxyisoleucine
    Aouadi, Kaiss
    Lajoix, Anne-Dominique
    Gross, Rene
    Praly, Jean-Pierre
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (01) : 61 - 71
  • [10] Analogues of insulin secretagogue (2S,3R,4S)-4-hydroxyisoleucine:: synthesis by 1,3-dipolar cycloaddition reactions of chiral nitrones to alkenes
    Aouadi, Kaiss
    Jeanneau, Erwann
    Msaddek, Moncef
    Praly, Jean-Pierre
    TETRAHEDRON-ASYMMETRY, 2008, 19 (09) : 1145 - 1152