岡山大学農学部Acta Medica Okayama0474-02549412005アルキン型リンカーを用いた糖鎖固相合成--薗頭反応による高反応部位の選択8184ENMinoruIzumiTwo new alkyne-type linkers having alkynylmethyloxy moieties were elaborated for solid-phase synthesis of oligosaccharide. A propargyl glycoside-type linker between a sugar residue and a solid support was formed by the Sonogashira reaction of a propargyl glycoside with polymer-supported iodobenzene. A propargyl ester-type linker was also constructed by the same reaction of a 4-(proparygyloxycarbonyl)benzyl glycoside with the latter. Both linkers are stable against acids such as TFA but can be readily cleaved with this acid after conversion to the corresponding alkyne-cobalt complex by treatment with Co2(CO)8. The latter ester linker is generally advantageous in that mild cleavage liberates a proceed only at spatially reactive sites on the solid support where the reagent accesses readily, so that the subsequent reactions including glycosylation on solid phase proceeded smoothly to result in high total yields of the desired oligosaccharides.No potential conflict of interest relevant to this article was reported.岡山大学農学部Acta Medica Okayama2186-77551062017半強制的な反復学習による基礎科目の徹底教育13ENMinoruIzumiGraduate School of Environmental and life Science, Okayama UniversityYoshiyukiMurataGraduate School of Environmental and life Science, Okayama University We employ the methodology of “Compulsory Repetitive Learning” to improve student learning and performance in fundamental subjects. It is a challenge for many universities to intrinsically motivate students and it is a demanding issue that a large part of students do not sufficiently do homework. Here, we let students solve the problems associated with the teaching immediately following each lecture. Through the usage of “Compulsory Repetitive Learning”, each student as well as the subject teacher(s) could monitor and evaluate the quality of student learning and performance.No potential conflict of interest relevant to this article was reported.Nature Publishing GroupActa Medica Okayama2045-2322712017Synthesis of Sulfo-Sialic Acid Analogues: Potent Neuraminidase Inhibitors in Regards to Anomeric Functionality8239ENChristopher J.VavrickGraduate School of Environmental and Life Science, Okayama UniversityChiakiMutoGraduate School of Environmental and Life Science, Okayama UniversityTomohisaHasunumaGraduate School of Science, Technology and Innovation, Kobe UniversityYoshinobuKimuraGraduate School of Environmental and Life Science, Okayama UniversityMichihiroArakiGraduate School of Science, Technology and Innovation, Kobe UniversityYanWuCAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of SciencesGeorge F.GaoCAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of SciencesHiroshiOhruiYokohama College of PharmacyMinoruIzumiGraduate School of Environmental and Life Science, Okayama UniversityHiromasaKiyotaGraduate School of Environmental and Life Science, Okayama University 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.No potential conflict of interest relevant to this article was reported.Japan Society for Bioscience, Biotechnology, and AgrochemistryActa Medica Okayama0916-84517142007Synthesis of lipid derivatives of pyrrole polyamide and their biological activity10781082ENMasahikoYamamotoChangjinZhuLuiYiZhengRongYoshieMiuraMinoruIzumiShuheiNakajimaKen-ichiTanamotoSakayuShimizuNaomichiBabaNovel fatty acyl and phospholipid derivatives of pyrrole polyamide were synthesized. Their cytotoxicity against a cancer cell line of MT-4 cells and those infected by human immunodeficiency virus (HIV) was examined. Although no anti-HIV activity was found, their cytotoxicitty against the cancer cells was significantly enhanced by introducing a lipophilic group into the pyrrole polyamide.No potential conflict of interest relevant to this article was reported.Japan Society for Bioscience, Biotechnology, and AgrochemistryActa Medica Okayama0916-84517132007Glucosylation of Sucrose Laurate with Cyclodextrin Glucanotransferase826829ENKatsuhideOkadaHaisuoZhaoMinoruIzumiShuheiNakajimaNaomichiBabaSucrose monolauroyl esters were found to serve as substrates for cyclodextrin glucanotransferase (CGTase)-catalyzed transglucosidation reactions, affording new sucrose esters that have an additional 1-3 glucose residues on the pyranose ring of the sucrose moiety in the ester.No potential conflict of interest relevant to this article was reported.Japan Society for Bioscience, Biotechnology, and AgrochemistryActa Medica Okayama0916-84517142007Three antinematodal diterpenes from Euphorbia kansui10861089ENJian-XiaoShiZhi-XuanLiTeruhikoNitodaMinoruIzumiHiroshiKanzakiNaomichiBabaKazuyoshiKawazuShuheiNakajimaThree compounds, 20-O-acetyl-[3-O-(2'E,4'Z)-deca-dienoyl]-ingenol (1), 20-O-acetyl-[5-O-(2'E,4'Z)-decadienoyl]-ingenol (2) and 3-O-(2'E,4'Z)-decadienoylingenol (3), were isolated from Euphorbia kansui under the bioassay-guided method. Each compound showed the same antinematodal activity against the nematode, Bursaphelenchus xylophilus, at a minimum effective dose (MED) of 5 mu g/cotton ball.No potential conflict of interest relevant to this article was reported.Oxford University Press (OUP)Acta Medica Okayama1347-69478512021Synthesis of (12R,13S)-pyriculariol and (12R,13S)-dihydropyriculariol revealed that the rice blast fungus, Pyricularia oryzae, produces these phytotoxins as racemates134142ENYutaNagashimaLaboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku UniversityAyakaSasakiLaboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku UniversityRyoyaHiraokaGraduate School of Environmental and Life Science, Okayama UniversityYukoOnodaGraduate School of Environmental and Life Science, Okayama UniversityKojiTanakaLaboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku UniversityZi-YiWangGraduate School of Environmental and Life Science, Okayama UniversityAtsukiKuwanaGraduate School of Environmental and Life Science, Okayama UniversityYukiSatoLaboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku UniversityYujiSuzukiLaboratory of Plant Nutrition and Function, Graduate School of Agricultural Science, Tohoku UniversityMinoruIzumiGraduate School of Environmental and Life Science, Okayama UniversityShigefumiKuwaharaLaboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku UniversityManabuNukinaProfessor Emeritus, Yamagata UniversityHiromasaKiyotaGraduate School of Environmental and Life Science, Okayama UniversitySynthesis 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.No potential conflict of interest relevant to this article was reported.