Faculty Profiles - IZUMI Minoru

Papers - IZUMI Minoru

Division display 1 - 20 of about 43 ／ All the affair displays >>

Synthesis of the A/D/E-ring Core Compounds of Maoecrystal V†. Reviewed International journal

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 88 ( 7 ) 733 - 741 2024.6

Fischer Glycosidation Using Organotitanium Catalyst ORGATIX Reviewed

Minoru Izumi, Nana Yanagida, Keita Kato, Mako Matsushita

HETEROCYCLES 106 ( 8 ) 1309 - 1309 2023.8

Synthesis of the C/D/E-ring core compound of maoecrystal V Reviewed

Shunki Katayama, Mitsuki Nishimoto, Tatsuya Ura, Taiki Ishimoto, Kousuke Ida, Yuki Sato, Christopher J. Vavricka, Minoru Izumi, Hiromasa Kiyota

Synthetic Communications 53 ( 10 ) 708 - 712 2023.3

Synthesis of the oxazolidinone fragment of thelepamide Reviewed

Naoki Ashida, Kousuke Ida, Yumi Koide, Christopher J. Vavricka, Minoru Izumi, Hiromasa Kiyota

NATURAL PRODUCT RESEARCH 36 ( 7 ) 1686 - 1692 2022.3

Language：English Publishing type：Research paper (scientific journal) Publisher：TAYLOR & FRANCIS LTD

Thelepamide, an unique ketide-amino acid isolated from a marine annelid wormThelepus crispus, has a unique oxazolidinone ring derived from cysteine, glycine and valine. Rareness in nature as well as promising bioactive possibility make the oxazolidinone ring an attractive synthetic target. The hydroxy oxazolidinone fragment of thelepamide was prepared by acid-catalysedN,O-acetal formation between a ketoamide and formaldehyde. Lactone-carbonyl selective isopropyl addition to an oxazilidine-dione under Grignard conditions also forms the target compound.

DOI： 10.1080/14786419.2020.1809398

Web of Science

researchmap

Evaluation of an improved antinematodal assay against the plantparasitic nematode Bursaphelenchus xylophilus and its application to an antinematodal activity study of synthetic 4-methylumbelliferyl glycoside Reviewed

Minoru Izumi, Kentaro Nakamura, Ayuko Ishizaka, Hiromasa Kiyota, Shuhei Nakajima

Nematological Research 51 ( 2 ) 33 - 36 2021.12

Synthesis of (12R,13S)-pyriculariol and (12R,13S)-dihydropyriculariol revealed that the rice blast fungus, Pyricularia oryzae, produces these phytotoxins as racemates Reviewed

Yuta Nagashima, Ayaka Sasaki, Ryoya Hiraoka, Yuko Onoda, Koji Tanaka, Zi-Yi Wang, Atsuki Kuwana, Yuki Sato, Yuji Suzuki, Minoru Izumi, Shigefumi Kuwahara, Manabu Nukina, Hiromasa Kiyota

Bioscience, Biotechnology, and Biochemistry 85 ( 1 ) 134 - 142 2021.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Oxford University Press (OUP)

<title>Abstract</title>
Synthesis of assumed natural (12R,13S)-enantiomers of pyriculariol (1) and dihydropyriculariol (2), phytotoxins isolated from rice blast disease fungus, Pyricularia oryzae, was achieved using Wittig reaction or microwave-assisted Stille coupling reaction as the key step. The synthesis revealed that the natural 1 and 2 are racemates. Foliar application test on a rice leaf indicated that both the salicylaldehyde core and side chain were necessary for phytotoxic activity. The fungus is found to produce optically active phytotoxins when incubated with rotary shaker, but racemic ones when cultured using an aerated jar fermenter.

DOI： 10.1093/bbb/zbaa002

researchmap

Microbial α-L-Rhamnosidases of Glycosyl Hydrolase Families GH78 and GH106 Have Broad Substrate Specificities toward α-L-Rhamnosyl- and α-L-Mannosyl-Linkages Reviewed

Feunai Agape Papalii Tautau, Minoru Izumi, Emiko Matsunaga, Yujiro Higuchi, Kaoru Takegawa

Journal of Applied Glycoscience 67 ( 3 ) 87 - 93 2020.9

Biosynthesis of β-(1→5)-Galactofuranosyl Chains of Fungal-Type and O-Mannose-Type Galactomannans within the Invasive Pathogen Aspergillus fumigatus. Reviewed International journal

Yuria Chihara, Yutaka Tanaka, Minoru Izumi, Daisuke Hagiwara, Akira Watanabe, Kaoru Takegawa, Katsuhiko Kamei, Nobuyuki Shibata, Kazuyoshi Ohta, Takuji Oka

mSphere 5 ( 1 ) 2020.1

Language：English

The pathogenic fungus Aspergillus fumigatus contains galactomannans localized on the surface layer of its cell walls, which are involved in various biological processes. Galactomannans comprise α-(1→2)-/α-(1→6)-mannan and β-(1→5)-/β-(1→6)-galactofuranosyl chains. We previously revealed that GfsA is a β-galactofuranoside β-(1→5)-galactofuranosyltransferase involved in the biosynthesis of β-(1→5)-galactofuranosyl chains. In this study, we clarified the biosynthesis of β-(1→5)-galactofuranosyl chains in A. fumigatus Two paralogs exist within A. fumigatus: GfsB and GfsC. We show that GfsB and GfsC, in addition to GfsA, are β-galactofuranoside β-(1→5)-galactofuranosyltransferases by biochemical and genetic analyses. GfsA, GfsB, and GfsC can synthesize β-(1→5)-galactofuranosyl oligomers at up to lengths of 7, 3, and 5 galactofuranoses within an established in vitro highly efficient assay of galactofuranosyltransferase activity. Structural analyses of galactomannans extracted from ΔgfsB, ΔgfsC, ΔgfsAC, and ΔgfsABC strains revealed that GfsA and GfsC synthesized all β-(1→5)-galactofuranosyl residues of fungal-type and O-mannose-type galactomannans and that GfsB exhibited limited function in A. fumigatus The loss of β-(1→5)-galactofuranosyl residues decreased the hyphal growth rate and conidium formation ability and increased the abnormal hyphal branching structure and cell surface hydrophobicity, but this loss is dispensable for sensitivity to antifungal agents and virulence toward immunocompromised mice.IMPORTANCE β-(1→5)-Galactofuranosyl residues are widely distributed in the subphylum Pezizomycotina of the phylum Ascomycota. Pezizomycotina includes many plant and animal pathogens. Although the structure of β-(1→5)-galactofuranosyl residues of galactomannans in filamentous fungi was discovered long ago, it remains unclear which enzyme is responsible for biosynthesis of this glycan. Fungal cell wall formation processes are complicated, and information concerning glycosyltransferases is essential for understanding them. In this study, we showed that GfsA and GfsC are responsible for the biosynthesis of all β-(1→5)-galactofuranosyl residues of fungal-type and O-mannose-type galactomannans. The data presented here indicate that β-(1→5)-galactofuranosyl residues are involved in cell growth, conidiation, polarity, and cell surface hydrophobicity. Our new understanding of β-(1→5)-galactofuranosyl residue biosynthesis provides important novel insights into the formation of the complex cell wall structure and the virulence of the members of the subphylum Pezizomycotina.

DOI： 10.1128/mSphere.00770-19

PubMed

researchmap

Chemo-enzymatic synthesis of p-nitrophenyl β-D-galactofuranosyl disaccharides from Aspergillus sp. fungal-type galactomannan Reviewed

Ryo Ota, Yumi Okamoto, Christopher J. Vavricka, Takuji Oka, Emiko Matsunaga, Kaoru Takegawa, Hiromasa Kiyota, Minoru Izumi

Carbohydrate Research 473 99 - 103 2019.2

Multigram-Scale and Column Chromatography-Free Synthesis of L-Azetidine-2-carboxylic Acid for the Synthesis of Nicotianamine and Its Derivatives Reviewed

Minoru Izumi, Tomohiro Takaishi, Kyosuke Wakisaka, Christopher J Vavricka, Hiromasa Kiyota

HETEROCYCLES 96 ( 12 ) 2126 - 2126 2018.12

Synthesis of Halogenated-4-Nitrophenyl 2-deoxy-2-halogeno-pyranosides via N-Halogenosuccinimide Activated Glucal Reviewed

Chieri Inoue, Yumi Okamoto, Christopher J. Vavricka, Hiromasa Kiyota, Minoru Izumi

NATURAL PRODUCT COMMUNICATIONS 13 ( 1 ) 85 - 87 2018.1

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：NATURAL PRODUCTS INC

Reaction of 3,4,6-tri-O-acetyl-a-glucal with silver 4-nitrophenolate in the presence of N-iodosuccinimide and N-bromosuccinimide produced (2,6-dihalo-4-nitro)phenyl 2-halo-2-deoxy-alpha-D-glycopyranosides. Although bromination and iodination of the 4-nitrophenyl group could not be avoided, the resulting (2,6-dihalo-4-nitro)phenylated compounds can be used as substrates or covalent glycosidase inhibitors after deprotection. The stereoselectivity and regioselectivity of the halogenation reactions are described.

Web of Science

researchmap

Synthesis of Sulfo-Sialic Acid Analogues: Potent Neuraminidase Inhibitors in Regards to Anomeric Functionality Reviewed

Christopher J. Vavricka, Chiaki Muto, Tomohisa Hasunuma, Yoshinobu Kimura, Michihiro Araki, Yan Wu, George F. Gao, Hiroshi Ohrui, Minoru Izumi, Hiromasa Kiyota

SCIENTIFIC REPORTS 7 ( 1 ) 13802 - 13808 2017.8

Language：English Publishing type：Research paper (scientific journal) Publisher：NATURE PUBLISHING GROUP

The design, synthesis and application of N-acetylneuraminic acid-derived compounds bearing anomeric sulfo functional groups are described. These novel compounds, which we refer to as sulfo-sialic acid analogues, include 2-decarboxy-2-deoxy-2-sulfo-N-acetylneuraminic acid and its 4-deoxy-3,4-dehydrogenated pseudoglycal. While 2-decarboxy-2-deoxy-2-sulfo-N-acetylneuraminic acid contains no further modifications of the 2-deoxy-pyranose ring, it is still a more potent inhibitor of avian-origin H5N1 neuraminidase (NA) and drug-resistant His275Tyr NA as compared to the oxocarbenium ion transition state analogue 2,3-dehydro-2-deoxy-N-acetylneuraminic acid. The sulfo-sialic acid analogues described in this report are also more potent inhibitors of influenza NA (up to 40-fold) and bacterial NA (up to 8.5-fold) relative to the corresponding anomeric phosphonic acids. These results confirm that this novel anomeric sulfo modification offers great potential to improve the potency of next-generation NA inhibitors including covalent inhibitors.

DOI： 10.1038/s41598-017-07836-y

Web of Science

researchmap

GfsA is a beta 1,5-galactofuranosyltransferase involved in the biosynthesis of the galactofuran side chain of fungal-type galactomannan in Aspergillus fumigatus Reviewed

Yukako Katafuchi, Qiushi Li, Yutaka Tanaka, Saki Shinozuka, Yohei Kawamitsu, Minoru Izumi, Keisuke Ekino, Keiji Mizuki, Kaoru Takegawa, Nobuyuki Shibata, Masatoshi Goto, Yoshiyuki Nomura, Kazuyoshi Ohta, Takuji Oka

GLYCOBIOLOGY 27 ( 6 ) 568 - 581 2017.6

Language：English Publishing type：Research paper (scientific journal) Publisher：OXFORD UNIV PRESS INC

Previously, we reported that GfsA is a novel galactofuranosyltransferase involved in the biosynthesis of O-glycan, the proper maintenance of fungal morphology, the formation of conidia and anti-fungal resistance in Aspergillus nidulans and A. fumigatus (Komachi Y et al., 2013. GfsA encodes a novel galactofuranosyltransferase involved in biosynthesis of galactofuranose antigen of O-glycan in Aspergillus nidulans and Aspergillus fumigatus. Mol. Microbiol. 90:1054-1073). In the present paper, to gain an in depth-understanding of the enzymatic functions of GfsA in A. fumigatus (AfGfsA), we established an in vitro assay to measure galactofuranosyltransferase activity using purified AfGfsA, UDP-alpha-d-galactofuranose as a sugar donor, and p-nitrophenyl-beta-d-galactofuranoside as an acceptor substrate. LC/MS, H-1-NMR and methylation analyses of the enzymatic products of AfGfsA revealed that this protein has the ability to transfer galactofuranose to the C-5 position of the beta-galactofuranose residue via a beta-linkage. AfGfsA requires a divalent cation of manganese for maximal activity and consumes UDP-alpha-d-galactofuranose as a sugar donor. Its optimal pH range is 6.5-7.5 and its optimal temperature range is 20-30A degrees C. H-1-NMR, C-13-NMR and methylation analyses of fungal-type galactomannan extracted from the a dagger AfgfsA strain revealed that AfGfsA is responsible for the biosynthesis of beta 1,5-galactofuranose in the galactofuran side chain of fungal-type galactomannan. Based on these results, we conclude that AfGfsA acts as a UDP-alpha-d-galactofuranose: beta-d-galactofuranoside beta 1,5-galactofuranosyltransferase in the biosynthetic pathway of galactomannans.

DOI： 10.1093/glycob/cwx028

Web of Science

researchmap

Product Selectivity of Esterification of L-Aspartic Acid and L-Glutamic Acid Using Chlorotrimethylsilane Reviewed

Tomohiro Takaishi, Minoru Izumi, Ryo Ota, Chieri Inoue, Hiromasa Kiyota, Koichi Fukase

NATURAL PRODUCT COMMUNICATIONS 12 ( 2 ) 247 - 249 2017.2

Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：NATURAL PRODUCTS INC

TMSCl works as an acid catalyst precursor for selective esterification of L-aspartic and L-glutamic acids in the presence of primary, secondary and tertiary alcohols. Although excess TMSCl was required for the completion of esterification, the resulting alkyl TMS ether could be azeotropically removed by simple evaporation with alcohol.

Web of Science

researchmap

Synthesis of the spiroacetal fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tu 4113 Reviewed

Hiroyuki Sakauchi, Emi Higashi, Yuko Shimizu, Mikiko Kojima, Yuko Asamitsu, Shigefumi Kuwahara, Minoru Izumi, Hiromasa Kiyota

HETEROCYCLIC COMMUNICATIONS 21 ( 6 ) 337 - 343 2015.12

Language：English Publishing type：Research paper (scientific journal) Publisher：WALTER DE GRUYTER GMBH

The spiroacetal [C(9)-C(20)] fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tu 4113, were prepared from a known bromo alcohol derived from (S)-citronellal, using thermodynamically controlled iodolactonization and spiroacetalization as the key steps.

DOI： 10.1515/hc-2015-0193

Web of Science

researchmap

Identification and Characterization of a Novel Galactofuranose-Specific beta-D-Galactofuranosidase from Streptomyces Species Reviewed

Emiko Matsunaga, Yujiro Higuchi, Kazuki Mori, Nao Yairo, Takuji Oka, Saki Shinozuka, Kosuke Tashiro, Minoru Izumi, Satoru Kuhara, Kaoru Takegawa

PLOS ONE 10 ( 9 ) 2015.9

Language：English Publishing type：Research paper (scientific journal) Publisher：PUBLIC LIBRARY SCIENCE

beta-D-galactofuranose (Galf) is a component of polysaccharides and glycoconjugates and its transferase has been well analyzed. However, no beta-D-galactofuranosidase (Galf-ase) gene has been identified in any organism. To search for a Galf-ase gene we screened soil samples and discovered a strain, identified as a Streptomyces species by the 16S ribosomal RNA gene analysis, that exhibits Galf-ase activity for 4-nitrophenyl beta-D-galactofuranoside (pNP-beta-D-Galf) in culture supernatants. By draft genome sequencing of the strain, named JHA19, we found four candidate genes encoding Galf-ases. Using recombinant proteins expressed in Escherichia coli, we found that three out of four candidates displayed the activity of not only Galf-ase but also alpha-L-arabinofuranosidase (Araf-ase), whereas the other one showed only the Galf-ase activity. This novel Galf-specific hydrolase is encoded by ORF1110 and has an optimum pH of 5.5 and a Km of 4.4 mM for the substrate pNP-beta-D-Galf. In addition, this enzyme was able to release galactose residue from galactomannan prepared from the filamentous fungus Aspergillus fumigatus, suggesting that natural polysaccharides could be also substrates. By the BLAST search using the amino acid sequence of ORF1110 Galf-ase, we found that there are homolog genes in both prokaryotes and eukaryotes, indicating that Galf-specific Galf-ases widely exist in microorganisms.

DOI： 10.1371/journal.pone.0137230

Web of Science

researchmap

Safe and convenient nitroxyl radical and imide dual catalyzed NaOCl oxidation of alcohols to aldehydes/ketones Reviewed

Naohiro Fukuda, Minoru Izumi, Tomomi Ikemoto

TETRAHEDRON LETTERS 56 ( 25 ) 3905 - 3908 2015.6

Language：English Publishing type：Research paper (scientific journal) Publisher：PERGAMON-ELSEVIER SCIENCE LTD

A novel and practical oxidation of alcohols to carbonyl compounds using NaOCl in the presence of catalytic amounts of imide compound and nitroxyl radical has been developed. A wide variety of aliphatic, benzylic primary alcohols, and secondary alcohols were oxidized to afford the corresponding aldehydes and ketones in up to 98% yield without undesired halogenation on aromatic rings or double bonds. The oxidation safely proceeded not only in the presence of K2CO3 but also by a slow addition of NaOCl without tedious pH adjustment. (C) 2015 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2015.04.115

Web of Science

researchmap

Pictet-Spengler Reaction Using Ion-Exchange Resin as a Catalyst and Support for 'Catch and Release' Purification

Minoru Izumi, Takeshi Kido, Miyu Murakami, Shuhei Nakajima, A. Ganesan

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 75 ( 2 ) 391 - 392 2011.2

Language：English Publishing type：Research paper (scientific journal) Publisher：TAYLOR & FRANCIS LTD

The Pictet-Spengler reaction between tryptamine and aldehydes was catalyzed by Dowex 50W-X4 acidic ion-exchange resin. The products were obtained from the resin in high purity by 'catch and release' without the need for separate chromatographic purification.

DOI： 10.1271/bbb.100770

Web of Science

researchmap

Analogues of the Nicotinic Acid Adenine Dinucleotide Phosphate (NAADP) Antagonist Ned-19 Indicate Two Binding Sites on the NAADP Receptor Reviewed

Daniel Rosen, Alexander M. Lewis, Akiko Mizote, Justyn M. Thomas, Parvinder K. Aley, Sridhar R. Vasudevan, Raman Parkesh, Antony Galione, Minoru Izumi, A. Ganesan, Grant C. Churchill

JOURNAL OF BIOLOGICAL CHEMISTRY 284 ( 50 ) 34930 - 34934 2009.12

Language：English Publishing type：Research paper (scientific journal) Publisher：AMER SOC BIOCHEMISTRY MOLECULAR BIOLOGY INC

Nicotinic acid adenine dinucleotide phosphate (NAADP) is a Ca(2+)-releasing messenger. Biological data suggest that its receptor has two binding sites: one high-affinity locking site and one low-affinity opening site. To directly address the presence and function of these putative binding sites, we synthesized and tested analogues of the NAADP antagonist Ned-19. Ned-19 itself inhibits both NAADP-mediated Ca(2+) release and NAADP binding. A fluorometry bioassay was used to assess NAADP-mediated Ca(2+) release, whereas a radioreceptor assay was used to assess binding to the NAAD Preceptor (only at the high-affinity site). In Ned-20, the fluorine is para rather than ortho as in Ned-19. Ned-20 does not inhibit NAADP-mediated Ca(2+) release but inhibits NAADP binding. Conversely, Ned-19.4 (a methyl ester of Ned-19) inhibits NAADP-mediated Ca(2+) release but cannot inhibit NAADP binding. Furthermore, Ned-20 prevents the self-desensitization response characteristic of NAADP in sea urchin eggs, confirming that this response is mediated by a high-affinity allosteric site to which NAADP binds in the radioreceptor assay. Collectively, these data provide the first direct evidence for two binding sites (one high-and one low affinity) on the NAADP receptor.

DOI： 10.1074/jbc.M109.016519

Web of Science

researchmap

Different behavior of artemisinin and tetraoxane in the oxidative degradation of phospholipid Reviewed

Naokazu Kumura, Hirotaka Furukawa, Arnold N. Onyango, Minoru Izumi, Shuhei Nakajima, Hideyuki Ito, Tsutomu Hatano, Hye-Sook Kim, Yusuke Wataya, Naomichi Baba

CHEMISTRY AND PHYSICS OF LIPIDS 160 ( 2 ) 114 - 120 2009.8

Language：English Publishing type：Research paper (scientific journal) Publisher：ELSEVIER IRELAND LTD

The reaction of trioxane and tetraoxane endoperoxides with unsaturated phospholipid I in the presence of Fe(II) was investigated in the absence of oxygen by means of tandem ESI-MS analysis. The spectral analyses for the reaction mixtures showed that artemisinin 2 with a trioxane structure gave no peak except that for the remaining intact phospholipid 1 (m/z 758.9), indicating that there was no structural change to 1. On other hand, the reaction mixture of I with tetraoxanes 3 and 4 afforded a number of new peaks (m/z 620-850) that were presumably assigned to oxidative degradation products originating from phospholipid 1. Since this reaction was completely inhibited by the addition of a phenolic antioxidant. the process was considered to involve some free radical species. The newly discovered marked differences in reactivity between the trioxane and the tetraoxanes possibly reflects their different anti-malarial mechanisms, and this reactivity may contribute to the classification of a number of anti-malarial endoperoxides whose mode of action is based on phospholipid oxidation. (C) 2009 Elsevier Ireland Ltd. All rights reserved.

DOI： 10.1016/j.chemphyslip.2009.04.005

Web of Science

researchmap

　 PREV - NEXT 　

< IZUMI Minoru >

Papers - IZUMI Minoru