Medicinal Enzyme Engineering Laboratory

established  Dec. 1st  2022

Published Papers
2024年
Integrated pathway mining and selection of an artificial CYP79-mediated bypass to improve benzylisoquinoline alkaloid biosynthesis
Musashi Takenaka, Kouhei Kamasaka, Kim Daryong, Keiko Tsuchikane, Seiha Miyazawa, Saeko Fujihana, Yoshimi Hori, Christopher J. Vavricka, Akira Hosoyama, Hiroko Kawasaki, Tomokazu Shirai, Michihiro Araki, Akira Nakagawa, Hiromichi Minami, Akihiko Kondo & Tomohisa Hasunuma
Microbial Cell Factories 23, Article number: 178 (2024)

Synthesis of the A/D/E-ring Core Compounds of Maoecrystal V
Hiroki Asao, Yasuharu Shimasaki, Ayaka Sasaki, Shunki Katayama, Kousuke Ida, Masaaki Kotake, Eriko Sato, Yuki Sato, Taiki Ishimoto, Minoru Izumi, Christopher J Vavricka, Shigefumi Kuwahara, Hiromasa Kiyota,
Bioscience, Biotechnology, and Biochemistry 2024;, zbae049


2023年
Synthesis of the C/D/E-Ring Core Compound of Maoecrystal V
Katayama, Shunki, Mitsuki Nishimoto, Tatsuya Ura, Taiki Ishimoto, Kousuke Ida, Yuki Sato, Christopher J. Vavricka, Minoru Izumi, and Hiromasa Kiyota,
Synthetic Communications 53, no. 10 (2023): 708–12.

Dark accumulation of downstream glycolytic intermediates initiates robust photosynthesis in cyanobacteria
Kenya Tanaka, Tomokazu Shirai, Christopher J Vavricka, Mami Matsuda, Akihiko Kondo, Tomohisa Hasunuma,
Plant Physiology, Volume 191, Issue 4, April 2023, Pages 2400–2413

3,4-Dihydroxyphenylacetaldehyde synthase evolved an ordered and distinct active site to promote elastic cuticle formation and blood intake in Aedes aegypti,
Jing Chen, Christopher Vavricka, Shuangshuang Wei et al.
28 March 2023

Online SFE-SFC-MS/MS colony screening: A high-throughput approach for optimizing (-)-limonene production,
Musashi Takekana, Takanobu Yoshida, Erika Yoshida, Sumika Ono, Shinnosuke Horie, Christopher J. Vavricka, Moe Hiratani, Kenji Tsuge, Jun Ishii, Yoshihiro Hayakawa, Akihiko Kondo, Tomohisa Hasunuma,
Journal of Chromatography B,Volume 1215,2023,123588,ISSN 1570-0232,


2022年

Simple and Rapid Non-ribosomal Peptide Synthetase Gene Assembly Using the SEAM-OGAB Method.
Jagadeesh V, Yoshida T, Uraji M, Okahashi N, Matsuda F, Vavricka CJ, Tsuge K, Kondo A.
ACS Synth Biol. 2023 Jan 20;12(1):305-318.

Synthesis and Neuraminidase Inhibitory Activity of Sialic Acid Analogues with Fluoro, Phosphono, and Sulfo Functionalities
Vavricka, C.J., Sriwilaijaroen, N., Suzuki, Y., Kiyota, H.
In: Suzuki, Y. (eds) Glycovirology. Methods in Molecular Biology, vol 2556. (2022).

Influenza A Virus Neuraminidase Inhibitors
Sriwilaijaroen, N., Vavricka, C.J., Kiyota, H., Suzuki, Y.
In: Suzuki, Y. (eds) Glycovirology. Methods in Molecular Biology, vol 2556.(2022).

Comprehensive Machine Learning Prediction of Extensive Enzymatic Reactions
Naoki Watanabe, Masaki Yamamoto, Masahiro Murata, Christopher J. Vavricka, Chiaki Ogino, Akihiko Kondo, and Michihiro Araki
The Journal of Physical Chemistry B 2022 126 (36), 6762-6770

Dark accumulation of downstream glycolytic intermediates confers robust initiation of photosynthesis in cyanobacteria.
Tanaka K, Shirai T, Vavricka CJ, et al.
bioRxiv; 2022.

Synthesis of the Oxazolidinone Fragment of Thelepamide.
Ashida, Naoki, Kousuke Ida, Yumi Koide, Christopher J. Vavricka, Minoru Izumi, and Hiromasa Kiyota.
Natural Product Research 36, no. 7 (2022): 1686–92.

Machine learning discovery of missing links that mediate alternative branches to plant alkaloids.
Vavricka, C.J., Takahashi, S., Watanabe, N. et al.
Nat Commun 13, 1405 (2022).


2021年Enhancing carbohydrate repartitioning into lipid and carotenoid by disruption of microalgae starch debranching enzyme.
Kato, Y., Oyama, T., Inokuma, K. et al.
Commun Biol 4, 450 (2021).

An ion-pair free LC-MS/MS method for quantitative metabolite profiling of microbial bioproduction systems.
Takenaka M, Yoshida T, Hori Y, Bamba T, Mochizuki M, Vavricka CJ, Hattori T, Hayakawa Y, Hasunuma T, Kondo A.
Talanta vol. 222 (2021).

Amino Acids | Aromatic Amino Acid Metabolism Across Species
Jianyong Li, Christopher J. Vavricka, Cihan Yang, Qian Han, Arthur J.L. Cooper
Encyclopedia of Biological Chemistry III (Third Edition),2021,Pages 22-42


2020年

Exploration and Evaluation of Machine Learning-Based Models for Predicting Enzymatic Reactions
Naoki Watanabe, Masahiro Murata, Teppei Ogawa, Christopher J. Vavricka, Akihiko Kondo, Chiaki Ogino, and Michihiro Araki
Journal of Chemical Information and Modeling 2020 60 (3), 1833-1843

Towards Improvement of Covalent Neuraminidase Inhibitors with Anomeric Substitution
Christopher J. Vavricka, Tatsuma Matsumoto, Hiromasa Kiyota
Trends in Glycoscience and Glycotechnology, 2020, 32 巻, 185 号, p. E1-E5, 公開日 2020/01/25,


2019年Light/dark cycling causes delayed lipid accumulation and increased photoperiod-based biomass yield by altering metabolic flux in oleaginous Chlamydomonas sp.
Kato, Y., Fujihara, Y., Vavricka, C.J. et al.
Biotechnol Biofuels 12, 39 (2019)

Single-Stage Astaxanthin Production Enhances the Nonmevalonate Pathway and Photosynthetic Central Metabolism in Synechococcus sp. PCC 7002
Tomohisa Hasunuma, Ayako Takaki, Mami Matsuda, Yuichi Kato, Christopher J. Vavricka, and Akihiko Kondo
ACS Synthetic Biology 2019 8 (12), 2701-2709

Dynamic Metabolomics for Engineering Biology: Accelerating Learning Cycles for Bioproduction.
Vavricka, C. J., Hasunuma, T., & Kondo, A.
Trends in biotechnology vol. 38,1 (2020): 68-82.

Mechanism-based tuning of insect 3,4-dihydroxyphenylacetaldehyde synthase for synthetic bioproduction of benzylisoquinoline alkaloids.
Vavricka, C.J., Yoshida, T., Kuriya, Y. et al.
Nat Commun 10, 2015 (2019).

Chemo-enzymatic synthesis of p-nitrophenyl β-D-galactofuranosyl disaccharides from Aspergillus sp. fungal-type galactomannan.
Ota, R., Okamoto, Y., Vavricka, C. J., Oka, T., Matsunaga, E., Takegawa, K., Kiyota, H., & Izumi, M.
Carbohydrate research vol. 473 (2019): 99-103


2018年Structural insight into the mechanism of neuraminidase inhibitor-resistant mutations in human-infecting H10N8 Influenza A virus
Babayemi O. Oladejo, Yuhai Bi, Christopher J. Vavricka, Chunrui Li, Yan Chai, Kun Xu, Liqiang Li, Zhe Lu, Jiandong Li, Gary Wong, Sankar Mohan, B. Mario Pinto, Haihai Jiang, Jianxun Qi, George Fu Gao, Po Tien, Yan Wu
bioRxiv 378075

Temperature enhanced succinate production concurrent with increased central metabolism turnover in the cyanobacterium Synechocystis sp. PCC 6803.
Hasunuma T, Matsuda M, Kato Y, Vavricka CJ, Kondo A.
Metabolic engineering vol. 48 (2018): 109-120.

Multigram-scale and column chromatography-free synthesis of L-azetidine-2-carboxylic acid for the synthesis of nicotianamine and its derivatives.
Takaishi, T, Wakisaka, K, Vavricka, CJ, Kiyota, H & Izumi, M
Heterocycles, vol. 96, no. 12, pp. 2126-2134.

Synthesis of Halogenated-4-Nitrophenyl 2-deoxy-2-halogeno-pyranosides via N -Halogenosuccinimide Activated Glucal.
Inoue C, Okamoto Y, Vavricka CJ, Kiyota H, Izumi M.
Natural Product Communications. 2018;13(1).


2017年Evolutionary engineering of salt-resistant Chlamydomonas sp. strains reveals salinity stress-activated starch-to-lipid biosynthesis switching.
Kato Y, Ho SH, Vavricka CJ, Chang JS, Hasunuma T, Kondo A.
Bioresource technology vol. 245,Pt B (2017): 1484-1490.

Xylomexicanins I and J: Limonoids with Unusual B/C Rings from Xylocarpus granatum
Yi-Bing Wu, Ya-Zhen Wang, Zhi-Yu Ni, Xia Qing, Qing-Wen Shi, Françoise Sauriol, Christopher J. Vavricka, Yu-Cheng Gu, and Hiromasa Kiyota
Journal of Natural Products 2017 80 (9), 2547-2550

Chemical and pharmacological research on the plants from genus Ajuga
Qing, Xia, Yan, Hui-Min, Ni, Zhi-Yu, Vavricka, Christopher J., Zhang, Man-Li, Shi, Qing-Wen, Gu, Yu-Cheng and Kiyota, Hiromasa.
Heterocyclic Communications, vol. 23, no. 4, 2017, pp. 245-268.

Synthesis of Sulfo-Sialic Acid Analogues: Potent Neuraminidase Inhibitors in Regards to Anomeric Functionality.
Vavricka, C.J., Muto, C., Hasunuma, T. et al.
Sci Rep 7, 8239 (2017).

Glycoform of a newly identified pollen allergen, Cha o 3, from Chamaecyparis obtusa (Japanese cypress, Hinoki)
Osada T, Maeda M, Tanabe C, Furuta K, Vavricka CJ, Sasaki E, Okano M, Kimura Y.
Carbohydrate research, 448, 18–23.

Occurrence of complex type free N-glycans with a single GlcNAc residue at the reducing termini in the fresh-water plant, Egeria densa
Maeda, M., Ebara, N., Tani, M. et al.
Glycoconj J 34, 229–240 (2017).

Xylomexicanins I and J: Limonoids with Unusual B/C Rings from Xylocarpus granatum
Yi-Bing Wu, Ya-Zhen Wang, Zhi-Yu Ni, Xia Qing, Qing-Wen Shi, Françoise Sauriol, Christopher J. Vavricka, Yu-Cheng Gu, and Hiromasa Kiyota
Journal of Natural Products 2017 80 (9), 2547-2550


2016年
Resistance to Mutant Group 2 Influenza Virus Neuraminidases of an Oseltamivir-Zanamivir Hybrid Inhibitor
Wu YGao F, Qi J, Bi YFu L, Mohan S, Chen Y, Li X, Pinto BM, Vavricka CJ, Tien P, Gao GF
J Virol 90 (2016): 1484-1490.

Structural features of N-glycans linked to glycoproteins expressed in three kinds of water plants: Predominant occurrence of the plant complex type N-glycans bearing Lewis a epitope.
Maeda M, Tani M, Yoshiie T, Vavricka CJ, Kimura Y.
Carbohydrate research vol. 435 (2016): 50-57.


2015年

Atypical group 1 neuraminidase pH1N1-N1 bound to a group 1 inhibitor
Ying Wu, Christopher J Vavricka, Yan Wu, Qing Li, Santosh Rudrawar, Robin J Thomson, Mark von Itzstein, George F Gao, Jianxun Qi
Protein & Cell, Volume 6, Issue 10, October 2015, Pages 771–773,


2014年

Structure of Influenza Virus N7: the Last Piece of the Neuraminidase “Jigsaw” Puzzle
Sun XLi QWu Y, Wang M, Liu Y, Qi J, Vavricka CJ, Gao GF
J Virol 88 2014

Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity.
Abdel-Mageed, W. M., Bayoumi, S. A., Chen, C., Vavricka, C. J., Li, L., Malik, A., Dai, H., Song, F., Wang, L., Zhang, J., Gao, G. F., Lv, Y., Liu, L., Liu, X., Sayed, H. M., & Zhang, L.
Bioorganic & medicinal chemistry vol. 22,7 (2014)

Tyrosine metabolic enzymes from insects and mammals: A comparative perspective.
Vavricka, C.J., Han, Q., Mehere, P., Ding, H., Christensen, B.M. and Li, J.
Insect Science, 21: 13-19.(2014)


2013年

Characterization of two distinct neuraminidases from avian-origin human-infecting H7N9 influenza viruses.
Wu, Y., Bi, Y., Vavricka, C. et al.
Cell Res 23, 1347–1355 (2013)

Functional and Structural Analysis of Influenza Virus Neuraminidase N3 Offers Further Insight into the Mechanisms of Oseltamivir Resistance.
Li QQi J, Wu Y, Kiyota H, Tanaka K, Suhara Y, Ohrui H, Suzuki Y, Vavricka CJ, Gao GF
J Virol 87(2013)

Induced opening of influenza virus neuraminidase N2 150-loop suggests an important role in inhibitor binding.
Wu, Y., Qin, G., Gao, F. et al.
Sci Rep 3, 1551 (2013).

Influenza neuraminidase operates via a nucleophilic mechanism and can be targeted by covalent inhibitors.
Vavricka, C., Liu, Y., Kiyota, H. et al.
Nat Commun 4, 1491 (2013).


2012年

Structural and functional characterization of neuraminidase-like molecule N10 derived from bat influenza A virus.
Li, Q., Sun, X., Li, Z., Liu, Y., Vavricka, C. J., Qi, J., & Gao, G. F.
Proceedings of the National Academy of Sciences of the United States of America, 109(46), 18897–18902.


2011年Structural and functional analysis of laninamivir and its octanoate prodrug reveals group specific mechanisms for influenza NA inhibition.
Vavricka CJ, Li Q, Wu Y, Qi J, Wang M, Liu Y, Gao F, Liu J, Feng E, He J, Wang J, Liu H, Jiang H, Gao GF.
PLoS pathogens vol. 7,10 (2011): e1002249.

Influenza A Virus N5 Neuraminidase Has an Extended 150-Cavity .
Wang MQi J, Liu Y, Vavricka CJ, Wu Y, Li Q, Gao GF
J Virol 85 (2011): e1002249.

Adventures and lessons of an American biochemist in China.
Vavricka C. J.
Protein & cell vol. 2,8 (2011): 601-3.

Special features of the 2009 pandemic swine-origin influenza A H1N1 hemagglutinin and neuraminidase.
Vavricka, C.J., Liu, Y., Li, Q. et al.
Chin. Sci. Bull. 56, 1747–1752 (2011).

What job can a bug give? A controversy over the arsenic-guzzling bacterium cultured by NASA.
Sun, M., Vavricka, C. J., & Zhu, B.
Protein & cell vol. 2,4 (2011): 261-3.

From L-dopa to dihydroxyphenylacetaldehyde: a toxic biochemical pathway plays a vital physiological function in insects.
Vavricka, C., Han, Q., Huang, Y., Erickson, S. M., Harich, K., Christensen, B. M., & Li, J.
PloS one vol. 6,1 e16124. 24 Jan. 2011

2009 Pandemic Influenza Virus: What Special for its HA and NA?
George F. Gao, Christopher J. Vavricka,
Antiviral Research,Volume 90, Issue 2,2011,Page A26,


2010年Novel Immunodominant Peptide Presentation Strategy: a Featured HLA-A*2402-Restricted Cytotoxic T-Lymphocyte Epitope Stabilized by Intrachain Hydrogen Bonds from Severe Acute Respiratory Syndrome Coronavirus Nucleocapsid Protein.
Liu JWu PGao F, Qi JKawana-Tachikawa A, Xie J, Vavricka CJ, Iwamoto ALi T, Gao GF
J Virol 84 2010

Tyrosine aminotransferase: biochemical and structural properties and molecular dynamics simulations,
Prajwalini Mehere, Qian Han, Justin A Lemkul, Christopher J Vavricka, Howard Robinson, David R Bevan, Jianyong Li,
Protein & Cell, Volume 1, Issue 11, November 2010, Pages 1023–1032,

The 2009 pandemic H1N1 neuraminidase N1 lacks the 150-cavity in its active site.
Li, Q., Qi, J., Zhang, W. et al.
Nat Struct Mol Biol 17, 1266–1268 (2010)

Melanization in living organisms: a perspective of species evolution.
Vavricka, C.J., Christensen, B.M. & Li, J.
Protein Cell 1, 830–841 (2010).

In silico characterization of the functional and structural modules of the hemagglutinin protein from the swine-origin influenza virus A (H1N1)-2009.
Sun, Y., Shi, Y., Zhang, W., Li, Q., Liu, D., Vavricka, C., Yan, J., & Gao, G. F.
Science China. Life sciences vol. 53,6 (2010): 633-42.

In silico characterization of the functional and structural modules of the hemagglutinin protein from the swine-origin influenza virus A (H1N1)-2009.
Sun, Y., Shi, Y., Zhang, W. et al.
Sci. China Life Sci. 53, 633–642 (2010).

Crystal structure of the swine-origin A (H1N1)-2009 influenza A virus hemagglutinin (HA) reveals similar antigenicity to that of the 1918 pandemic virus
Wei Zhang, Jianxun Qi, Yi Shi, Qing Li, Feng Gao, Yeping Sun, Xishan Lu, Qiong Lu, Christopher J Vavricka, Di Liu, Jinghua Yan, George F Gao
Protein & Cell, Volume 1, Issue 5, May 2010, Pages 459–467

Purification and N-Glycosylation Analysis of Melanoma Antigen Dopachrome Tautomerase.
Vavricka, C.J., Ray, K.W., Christensen, B.M. et al.
Protein J 29, 204–212 (2010).


2009年

Mass Spectrometric Analysis of Tyrosine Metabolic Enzymes
CJ Vavricka
Virginia Tech(2009).


2007年
Proteomic analysis of N-glycosylation in mosquito dopachrome conversion enzyme.
Li, J. S., Vavricka, C. J., Christensen, B. M., & Li, J.
Proteomics vol. 7,15 (2007): 2557-69.


2006年
The matrix of ancient biofilms modulates stress tolerance
Richard F. Helm, Jody Jervis, Deborah Wright, Christopher J. Vavricka, Malcolm Potts
Volume20, Issue4, Experimental Biology 2006 (Part I), March 2006, Pages A516-A516


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