457
Views
79
CrossRef citations to date
0
Altmetric
Original Articles

Enzymatic Production of trans-4-Hydroxy-L-proline by Regio- and Stereospecific Hydroxylation of L-Proline

, &
Pages 746-750 | Received 15 Oct 1999, Accepted 24 Nov 1999, Published online: 22 May 2014

Keep up to date with the latest research on this topic with citation updates for this article.

Read on this site (1)

Ryotaro Hara, Naoko Uchiumi, Naoko Okamoto & Kuniki Kino. (2014) Regio- and stereoselective oxygenation of proline derivatives by using microbial 2-oxoglutarate-dependent dioxygenases. Bioscience, Biotechnology, and Biochemistry 78:8, pages 1384-1388.
Read now

Articles from other publishers (78)

Yu Gong, Ruiqi Wang, Ling Ma, Shuo Wang, Changgeng Li & Qingyang Xu. (2023) Optimization of trans-4-hydroxyproline synthesis pathway by rearrangement center carbon metabolism in Escherichia coli. Microbial Cell Factories 22:1.
Crossref
Christian R. ZwickIIIIII & Hans Renata. (2023) Overview of Amino Acid Modifications by Iron- and α-Ketoglutarate-Dependent Enzymes. ACS Catalysis 13:7, pages 4853-4865.
Crossref
Xiaoyan Hu, Xue Huang, Jiao Liu, Ping Zheng, Weimin Gong & Lin Yang. (2023) Structures of L -proline trans -hydroxylase reveal the catalytic specificity and provide deeper insight into AKG-dependent hydroxylation . Acta Crystallographica Section D Structural Biology 79:4, pages 318-325.
Crossref
Zhenyu Zhang, Weike Su, Yunyun Bao, Qianqian Huang, Kai Ye, Pengfu Liu & Xiaohe Chu. (2022) Modular reconstruction and optimization of the trans-4-hydroxy-L-proline synthesis pathway in Escherichia coli. Microbial Cell Factories 21:1.
Crossref
Erika Tassano, Charles Moore, Solene Dussauge, Alexandra Vargas & Radka Snajdrova. (2022) Discovery of New Fe(II)/α-Ketoglutarate-Dependent Dioxygenases for Oxidation of l -Proline . Organic Process Research & Development 26:7, pages 1996-2003.
Crossref
Eleni Theodosiou, Adrian Tüllinghoff, Jörg Toepel & Bruno Bühler. (2022) Exploitation of Hetero- and Phototrophic Metabolic Modules for Redox-Intensive Whole-Cell Biocatalysis. Frontiers in Bioengineering and Biotechnology 10.
Crossref
P. Ferreira, P.A. Fernandes & M.J. Ramos. (2022) The archaeal non-heme iron-containing Sulfur Oxygenase Reductase. Coordination Chemistry Reviews 455, pages 214358.
Crossref
Kiran S. Dalal, Girish B. Pendharkar, Dipak S. Dalal & Bhushan L. Chaudhari. 2022. Industrial Microbiology and Biotechnology. Industrial Microbiology and Biotechnology 335 378 .
Rajesh Kumar, Carlos A. Martinez & John W. Wong. 2022. Green Chemistry in Drug Discovery. Green Chemistry in Drug Discovery 375 401 .
Zhenyu Zhang, Pengfu Liu, Weike Su, Huawei Zhang, Wenqian Xu & Xiaohe Chu. (2021) Metabolic engineering strategy for synthetizing trans-4-hydroxy-l-proline in microorganisms. Microbial Cell Factories 20:1.
Crossref
Ryotaro Hara, Yuta Nakajima, Hiroaki Yanagawa, Ryo Gawasawa, Izumi Hirasawa & Kuniki Kino. (2021) Enzymatic Synthesis of l - threo -β-Hydroxy-α-Amino Acids via Asymmetric Hydroxylation Using 2-Oxoglutarate-Dependent Hydroxylase from Sulfobacillus thermotolerans Strain Y0017 . Applied and Environmental Microbiology 87:20.
Crossref
Judith Münch, Pascal Püllmann, Wuyuan Zhang & Martin J. Weissenborn. (2021) Enzymatic Hydroxylations of sp 3 -Carbons . ACS Catalysis 11:15, pages 9168-9203.
Crossref
Fabian Brandenburg, Eleni Theodosiou, Carolin Bertelmann, Marcel Grund, Stephan Klähn, Andreas Schmid & Jens O. Krömer. (2021) Trans-4-hydroxy-L-proline production by the cyanobacterium Synechocystis sp. PCC 6803. Metabolic Engineering Communications 12, pages e00155.
Crossref
Xiulai Chen, Juyang Yi, Jia Liu, Qiuling Luo & Liming Liu. (2020) Enzymatic production of trans ‐4‐hydroxy‐ l ‐proline by proline 4‐hydroxylase . Microbial Biotechnology 14:2, pages 479-487.
Crossref
Xiulai Chen, Juyang Yi, Wei Song, Jia Liu, Qiuling Luo & Liming Liu. (2020) Chassis engineering of Escherichia coli for trans ‐4‐hydroxy‐ l ‐proline production . Microbial Biotechnology 14:2, pages 392-402.
Crossref
Liangzhen Jiang, Jing Pang, Lixia Yang, Wei Li, Lili Duan, Guolin Zhang & Yinggang Luo. (2021) Engineering endogenous l-proline biosynthetic pathway to boost trans-4-hydroxy-l-proline production in Escherichia coli. Journal of Biotechnology 329, pages 104-117.
Crossref
Sjoerd Slagman & Wolf-Dieter Fessner. (2021) Biocatalytic routes to anti-viral agents and their synthetic intermediates. Chemical Society Reviews 50:3, pages 1968-2009.
Crossref
Jingxuan Qiu, Haishuang Huang, Hui He, Haoyou Liu, Shen Hu, Jiaming Han, Ying Guo & Peng Wang. (2020) Measurement and Correlation of trans -4-Hydroxy- l -proline Solubility in Sixteen Individual Solvents and a Water + Acetonitrile Binary Solvent System . Journal of Chemical & Engineering Data 66:1, pages 575-587.
Crossref
Shuke Wu, Radka Snajdrova, Jeffrey C. Moore, Kai Baldenius & Uwe T. Bornscheuer. (2020) Biocatalysis: Enzymatic Synthesis for Industrial Applications. Angewandte Chemie International Edition 60:1, pages 88-119.
Crossref
Shuke Wu, Radka Snajdrova, Jeffrey C. Moore, Kai Baldenius & Uwe T. Bornscheuer. (2020) Biokatalyse: Enzymatische Synthese für industrielle Anwendungen. Angewandte Chemie 133:1, pages 89-123.
Crossref
Sergio Martínez-Rodríguez, Jesus M. Torres, Pilar Sánchez & Esperanza Ortega. (2020) Overview on Multienzymatic Cascades for the Production of Non-canonical α-Amino Acids. Frontiers in Bioengineering and Biotechnology 8.
Crossref
Ryotaro Hara & Kuniki Kino. (2020) Enzymatic reactions and microorganisms producing the various isomers of hydroxyproline. Applied Microbiology and Biotechnology 104:11, pages 4771-4779.
Crossref
Mengfei Long, Meijuan XuZhenfeng MaXuewei PanJiajia YouMengkai HuYu ShaoTaowei YangXian ZhangZhiming Rao. (2020) Significantly enhancing production of trans -4-hydroxy- l -proline by integrated system engineering in Escherichia coli . Science Advances 6:21.
Crossref
Wei Song, Xiulai Chen, Jing Wu, Jianzhong Xu, Weiguo Zhang, Jia Liu, Jian Chen & Liming Liu. (2020) Biocatalytic derivatization of proteinogenic amino acids for fine chemicals. Biotechnology Advances 40, pages 107496.
Crossref
Tristan J. Smart, Refaat B. Hamed, Timothy D.W. Claridge & Christopher J. Schofield. (2020) Studies on the selectivity of proline hydroxylases reveal new substrates including bicycles. Bioorganic Chemistry 94, pages 103386.
Crossref
Jing Zhao, Chao Liu, Xuan Guo, Jinyu Wang, Haiping Liu, Ping Zheng, Jibin Sun & Yanhe Ma. (2019) Efficient production of trans-3-hydroxyproline by a bacterial trans-3-proline hydroxylase and characterization of enzymatic properties. Biochemical Engineering Journal 147, pages 57-61.
Crossref
Mattia Lazzarotto, Lucas Hammerer, Michael Hetmann, Annika Borg, Luca Schmermund, Lorenz Steiner, Peter Hartmann, Ferdinand Belaj, Wolfgang Kroutil, Karl Gruber & Michael Fuchs. (2019) Chemoenzymatic Total Synthesis of Deoxy‐, epi ‐, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones . Angewandte Chemie International Edition 58:24, pages 8226-8230.
Crossref
Mattia Lazzarotto, Lucas Hammerer, Michael Hetmann, Annika Borg, Luca Schmermund, Lorenz Steiner, Peter Hartmann, Ferdinand Belaj, Wolfgang Kroutil, Karl Gruber & Michael Fuchs. (2019) Chemoenzymatische Totalsynthese von Deoxy‐, epi ‐ und Podophyllotoxin sowie biokatalytische kinetische Racematspaltung von Dibenzylbutyrolactonen . Angewandte Chemie 131:24, pages 8310-8315.
Crossref
Xiaoran Jing, Xinye Wang, Wenli Zhang, Jianhong An, Pengjie Luo, Yao Nie & Yan Xu. (2019) Highly Regioselective and Stereoselective Hydroxylation of Free Amino Acids by a 2-Oxoglutarate-Dependent Dioxygenase from Kutzneria albida . ACS Omega 4:5, pages 8350-8358.
Crossref
Christopher K Prier & Birgit Kosjek. (2019) Recent preparative applications of redox enzymes. Current Opinion in Chemical Biology 49, pages 105-112.
Crossref
Christin Peters & Rebecca Buller. (2019) Industrial Application of 2-Oxoglutarate-Dependent Oxygenases. Catalysts 9:3, pages 221.
Crossref
Chao Liu, Jing Zhao, Jiao Liu, Xuan Guo, Deming Rao, Haiping Liu, Ping Zheng, Jibin Sun & Yanhe Ma. (2018) Simultaneously improving the activity and thermostability of a new proline 4-hydroxylase by loop grafting and site-directed mutagenesis. Applied Microbiology and Biotechnology 103:1, pages 265-277.
Crossref
Xing-Chu Wang, Jiao Liu, Jing Zhao, Xiao-Meng Ni, Ping Zheng, Xuan Guo, Cun-Min Sun, Ji-Bin Sun & Yan-He Ma. (2018) Efficient production of trans-4-hydroxy-l-proline from glucose using a new trans-proline 4-hydroxylase in Escherichia coli. Journal of Bioscience and Bioengineering 126:4, pages 470-477.
Crossref
Md. Saiful IslamThomas M. LeissingRasheduzzaman ChowdhuryRichard J. HopkinsonChristopher J. Schofield. (2018) 2-Oxoglutarate-Dependent Oxygenases. Annual Review of Biochemistry 87:1, pages 585-620.
Crossref
H.-L. Zhang, C. Zhang, C.-H. Pei, M.-N. Han, Z.-D. Xu, C.-H. Li & W. Li. (2018) Efficient production of trans -4-Hydroxy- l -proline from glucose by metabolic engineering of recombinant Escherichia coli . Letters in Applied Microbiology 66:5, pages 400-408.
Crossref
Shu-Shan Gao, Nathchar Naowarojna, Ronghai Cheng, Xueting Liu & Pinghua Liu. (2018) Recent examples of α-ketoglutarate-dependent mononuclear non-haem iron enzymes in natural product biosyntheses. Natural Product Reports 35:8, pages 792-837.
Crossref
Kequan Chen, Yang Pang, Bowen Zhang, Jiao Feng, Sheng Xu, Xin Wang & Pingkai Ouyang. (2017) Process optimization for enhancing production of cis-4-hydroxy-l-proline by engineered Escherichia coli. Microbial Cell Factories 16:1.
Crossref
Baixue Lin & Yong Tao. (2017) Whole-cell biocatalysts by design. Microbial Cell Factories 16:1.
Crossref
Ryotaro Hara, Kai Yamagata, Ryoma Miyake, Hiroshi Kawabata, Hisatoshi Uehara & Kuniki Kino. (2017) Discovery of Lysine Hydroxylases in the Clavaminic Acid Synthase-Like Superfamily for Efficient Hydroxylysine Bioproduction. Applied and Environmental Microbiology 83:17.
Crossref
Johanna Mattay & Wolfgang Hüttel. (2017) Pipecolic Acid Hydroxylases: A Monophyletic Clade among cis -Selective Bacterial Proline Hydroxylases that Discriminates l -Proline . ChemBioChem 18:15, pages 1523-1528.
Crossref
Tong-Xin Zhao, Mei Li, Xiang Zheng, Cheng-Hua Wang, Hong-Xin Zhao, Chong Zhang & Xin-Hui Xing. (2017) Improved production of trans-4-hydroxy-l-proline by chromosomal integration of the Vitreoscilla hemoglobin gene into recombinant Escherichia coli with expression of proline-4-hydroxylase. Journal of Bioscience and Bioengineering 123:1, pages 109-115.
Crossref
Jinxia Wang, Zhenyu Zhang, Hedong Liu, Fubao Fuelbiol Sun, Chun Yue, Jinguang Hu & Chundi Wang. (2016) Construction and optimization of trans -4-hydroxy-L-proline production recombinant E. coli strain taking the glycerol as carbon source . Journal of Chemical Technology & Biotechnology 91:9, pages 2389-2398.
Crossref
Jun Ogawa, Makoto Hibi & Shigenobu Kishino. 2016. Green Biocatalysis. Green Biocatalysis 545 555 .
Ryotaro Hara, Saki Kitatsuji, Kai Yamagata & Kuniki Kino. (2015) Development of a multi-enzymatic cascade reaction for the synthesis of trans-3-hydroxy-l-proline from l-arginine. Applied Microbiology and Biotechnology 100:1, pages 243-253.
Crossref
Shigeru Nakamori. 2017. Amino Acid Fermentation. Amino Acid Fermentation 35 53 .
Eleni Theodosiou, Oliver Frick, Bruno Bühler & Andreas Schmid. (2015) Metabolic network capacity of Escherichia coli for Krebs cycle-dependent proline hydroxylation. Microbial Cell Factories 14:1.
Crossref
Kento Koketsu, Yasuhito Shomura, Kei Moriwaki, Mikiro Hayashi, Satoshi Mitsuhashi, Ryotaro Hara, Kuniki Kino & Yoshiki Higuchi. (2014) Refined Regio- and Stereoselective Hydroxylation of l -Pipecolic Acid by Protein Engineering of l -Proline cis -4-Hydroxylase Based on the X-ray Crystal Structure . ACS Synthetic Biology 4:4, pages 383-392.
Crossref
Yulan Yi, Huakai Sheng, Zhimin Li & Qin Ye. (2014) Biosynthesis of trans-4-hydroxyproline by recombinant strains of Corynebacterium glutamicum and Escherichia coli. BMC Biotechnology 14:1.
Crossref
Damien Baud, Pierre‐Loïc Saaidi, Adam Monfleur, Marine Harari, Julien Cuccaro, Aurélie Fossey, Marielle Besnard, Adrien Debard, Aline Mariage, Virginie Pellouin, Jean‐Louis Petit, Marcel Salanoubat, Jean Weissenbach, Véronique de Berardinis & Anne Zaparucha. (2014) Synthesis of Mono‐ and Dihydroxylated Amino Acids with New α‐Ketoglutarate‐Dependent Dioxygenases: Biocatalytic Oxidation of CH Bonds. ChemCatChem 6:10, pages 3012-3017.
Crossref
Makoto Hibi & Jun Ogawa. (2014) Characteristics and biotechnology applications of aliphatic amino acid hydroxylases belonging to the Fe(II)/α-ketoglutarate-dependent dioxygenase superfamily. Applied Microbiology and Biotechnology 98:9, pages 3869-3876.
Crossref
Andreas Karau & Ian Grayson. 2014. Biotechnology of Food and Feed Additives. Biotechnology of Food and Feed Additives 189 228 .
Thi Mai Hoa Bach & Hiroshi Takagi. (2013) Properties, metabolisms, and applications of l-proline analogues. Applied Microbiology and Biotechnology 97:15, pages 6623-6634.
Crossref
Wolfgang Hüttel. (2013) Biocatalytic Production of Chemical Building Blocks in Technical Scale with α‐Ketoglutarate‐Dependent Dioxygenases. Chemie Ingenieur Technik 85:6, pages 809-817.
Crossref
Francesco Falcioni, Lars M. Blank, Oliver Frick, Andreas Karau, Bruno Bühler & Andreas Schmid. (2013) Proline Availability Regulates Proline-4-Hydroxylase Synthesis and Substrate Uptake in Proline-Hydroxylating Recombinant Escherichia coli. Applied and Environmental Microbiology 79:9, pages 3091-3100.
Crossref
H. Suzuki. 2013. Microbial Production of Food Ingredients, Enzymes and Nutraceuticals. Microbial Production of Food Ingredients, Enzymes and Nutraceuticals 385 412 .
Manfred Schrewe, Mattijs K. Julsing, Bruno Bühler & Andreas Schmid. (2013) Whole-cell biocatalysis for selective and productive C–O functional group introduction and modification. Chemical Society Reviews 42:15, pages 6346.
Crossref
Thi Mai Hoa Bach, Ryotaro Hara, Kuniki Kino, Iwao Ohtsu, Nobuyuki Yoshida & Hiroshi Takagi. (2012) Microbial production of N-acetyl cis-4-hydroxy-l-proline by coexpression of the Rhizobium l-proline cis-4-hydroxylase and the yeast N-acetyltransferase Mpr1. Applied Microbiology and Biotechnology 97:1, pages 247-257.
Crossref
Sergey V. Smirnov, Pavel M. Sokolov, Tomohiro Kodera, Masakazu Sugiyama, Makoto Hibi, Sakayu Shimizu, Kenzo Yokozeki & Jun Ogawa. (2012) A novel family of bacterial dioxygenases that catalyse the hydroxylation of free l-amino acids. FEMS Microbiology Letters 331:2, pages 97-104.
Crossref
Juquan JiangLynnette C. Johnson, John KnightMichael F. Callahan, Travis J. Riedel, Ross P. HolmesW. Todd Lowther. (2012) Metabolism of [ 13 C 5 ]hydroxyproline in vitro and in vivo: implications for primary hyperoxaluria . American Journal of Physiology-Gastrointestinal and Liver Physiology 302:6, pages G637-G643.
Crossref
K. Robins, A. Osorio-Lozada, M. Avi & M. Richter. 2012. Comprehensive Chirality. Comprehensive Chirality 481 515 .
Christian Klein & Wolfgang Hüttel. (2011) Tertiary alcohol preferred: Hydroxylation of trans -3-methyl-L-proline with proline hydroxylases . Beilstein Journal of Organic Chemistry 7, pages 1643-1647.
Crossref
F. Özde Ütkür, Sushil Gaykawad, Bruno Bühler & Andreas Schmid. (2010) Regioselective aromatic hydroxylation of quinaldine by water using quinaldine 4-oxidase in recombinant Pseudomonas putida. Journal of Industrial Microbiology & Biotechnology 38:8, pages 1067-1077.
Crossref
Christian Klein & Wolfgang Hüttel. (2011) A Simple Procedure for Selective Hydroxylation of L ‐Proline and L ‐Pipecolic Acid with Recombinantly Expressed Proline Hydroxylases . Advanced Synthesis & Catalysis 353:8, pages 1375-1383.
Crossref
Stefanie Wenda, Sabine Illner, Annett Mell & Udo Kragl. (2011) Industrial biotechnology—the future of green chemistry?. Green Chemistry 13:11, pages 3007.
Crossref
Lars M. BlankBirgitta E. EbertKatja BuehlerBruno Bühler. (2010) Redox Biocatalysis and Metabolism: Molecular Mechanisms and Metabolic Network Analysis. Antioxidants & Redox Signaling 13:3, pages 349-394.
Crossref
Shin‐Ichi Hashimoto, Satoshi Koizumi & Akio Ozaki. 2010. Asymmetric Catalysis on Industrial Scale. Asymmetric Catalysis on Industrial Scale 301 320 .
Kazuhiko Tabata & Satoshi Koizumi. 2010. Biotechnology in Functional Foods and Nutraceuticals. Biotechnology in Functional Foods and Nutraceuticals 127 138 .
Robert M. Johnston, Linda N. Chu, Mark Liu, Steven L. Goldberg, Animesh Goswami & Ramesh N. Patel. (2009) Hydroxylation of l-proline to cis-3-hydroxy-l-proline by recombinant Escherichia coli expressing a synthetic l-proline-3-hydroxylase gene. Enzyme and Microbial Technology 45:6-7, pages 484-490.
Crossref
Ryotaro Hara & Kuniki Kino. (2009) Characterization of novel 2-oxoglutarate dependent dioxygenases converting l-proline to cis-4-hydroxy-l-proline. Biochemical and Biophysical Research Communications 379:4, pages 882-886.
Crossref
Jens Müller & Martin Bröring. 2008. Iron Catalysis in Organic Chemistry. Iron Catalysis in Organic Chemistry 29 72 .
H. Mizoguchi, Y. Sawano, J.-i. Kato & H. Mori. (2008) Superpositioning of Deletions Promotes Growth of Escherichia coli with a Reduced Genome. DNA Research 15:5, pages 277-284.
Crossref
Mattijs K Julsing, Sjef Cornelissen, Bruno Bühler & Andreas Schmid. (2008) Heme-iron oxygenases: powerful industrial biocatalysts?. Current Opinion in Chemical Biology 12:2, pages 177-186.
Crossref
Laszlo N. Csonka & Thomas Leisinger. (2007) Biosynthesis of Proline. EcoSal Plus 2:2.
Crossref
Pericles Stavropoulos, Remle Çelenligil‐Çetin, Salma Kiani, Amy Tapper, Devender Pinnapareddy & Patrina Paraskevopoulou. 2005. Handbook of C–H Transformations. Handbook of C–H Transformations 497 651 .
Bruno Bühler & Andreas Schmid. (2004) Process implementation aspects for biocatalytic hydrocarbon oxyfunctionalization. Journal of Biotechnology 113:1-3, pages 183-210.
Crossref
Jun Ogawa & Sakayu Shimizu. (2002) Industrial microbial enzymes: their discovery by screening and use in large-scale production of useful chemicals in Japan. Current Opinion in Biotechnology 13:4, pages 367-375.
Crossref
Ian J. Clifton, Li‐Ching Hsueh, Jack E. Baldwin, Karl Harlos & Christopher J. Schofield. (2002) Structure of proline 3‐hydroxylase. European Journal of Biochemistry 268:24, pages 6625-6636.
Crossref
TAKESHI SHIBASAKI, SHINICHI HASHIMOTO, HIDEO MORI & AKIO OZAKI. (2000) Construction of a Novel Hydroxyproline-Producing Recombinant Escherichia coli by Introducing a Proline 4-Hydroxylase Gene.. Journal of Bioscience and Bioengineering 90:5, pages 522-525.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.