1989 年度実績報告書

生体機能物質の生合成機構とその応用に関する研究

研究課題

研究課題/領域番号	63303003
研究機関	北海道大学
研究代表者	村井章夫北海道大学, 理学部, 教授 (20000838)
研究分担者	丹羽治樹名古屋大学, 理学部, 助教授 (20135297) 野老山喬大阪市立大学, 理学部, 教授 (90046938) 三川潮東京大学, 薬学部, 教授 (60012613) 柿澤寛筑波大学, 化学系, 教授 (50015492) 高杉光雄北海道大学, 理学部, 教授 (70000833)
キーワード	グリシノエクレピンA / 生合成 / 生合成推定経路
研究概要	1.大豆シスト線虫ふ化促進物質グリシノエクレピンAの生合成推定経路による合成においてA/B環部を完成させ、C/D環部の構築を残すのみとなった(村井)。2.重水素で標識したブラシニンは、シクロブラシニンとスピロブラシニンに効率よく取り込まれた(高杉)3.アミジグサより生合成的に興味深いジテルペン5種を単離した(柿澤)。4.多重標識マロン酸を用いて芳香族ポリケチド鎖の延長に関わるマロニルCoAのメチレン水素の芳香化における脱離様式を検討した所、オルセリン酸生合成酸素では立体選択性を認めることが出来なかった(三川)。5.ニトロオレフィンの共役付加反応を利用した方法による生合成モデル前駆体の効率的合成に成功した(野老山)。6.ピロリチジンアルカロイドによる化学発癌の初期過程の研究の一環としてデビドロモノクロタリンと各種ヌクレオジドノ反応を行なった(丹羽)。7.その他、HMG-CoA還元酵素阻害活性を持つコンパクチンの生合成仮想中間体の新合成法の発立(平間)、ヘキサプレニルニリン酸合成酵素の2つの必須タンパク成分の会合による活性複合体形成の証明(小倉)、ゲラニルニリン酸の8位のメチル基に鎮長の違うアルコキシ基を導入した基質についてFEP合成酵素反応を試み、各基質の反応性の比較と生成物の分析を行なった(槇)。抗生物質セルレニンと脂肪酸合成酵素の作用機構の解明(川口)。2デオキシン-scyllo-イノソ-スの無細胞生合成系の構築(柿沼)。マメ科植物メドハギより植物の葉を夜間開かせる活性化合物の2種の単離、構造決定、全合成(志津里)。パリトキシンカルボン酸の分離と構造活性相関(上村)。シソ葉の紫色色素の構造決定(後藤)。インドネシア産ガマからの新アルカロイドの単離(徳山)。大豆の葉からの新規ポリプレノ-ルの単離、構造決定(菅)。生合成研究に有用な前駆体の合成(白浜、野副、冨士、伊東、香月)。

研究成果

(34件)

すべてその他

すべて文献書誌 (34件)

[文献書誌] M.Takasugi: "Brassicanals A and B,Novel Sulfur-containing Phytoalexins from the Chinese Cabbage Brassica compestris L.ssp.pekinensis" Chemistry Letters. 209-210 (1990)
[文献書誌] M.Takasugi: "4-Methoxybrassinin,a Sulfur-containing Phytoalexin from Brassica oleraces" Phytochemistry.
[文献書誌] K.Ogura: "Protection of Hexaprenyl Diphosphate Synthase of Micrococcus luteus B-P 26 against Inactivation by Sulphydryl Reagents and Arginine-specific Reagents" Biochem.Biophys.Acta. 995. 138-143 (1989)
[文献書誌] K.Ogura: "The Biosynthesis of Dehydrolichyl Phosphates by Rat Liver Microsomes" Biochem.Biophys.Acta. 1002. 218-224 (1989)
[文献書誌] K.Ogura: "Artificially Elicited Capabilities of Enzymes and Their Application in Natural Product Chemistry" Pure Apple.Chem.61. 477-480 (1989)
[文献書誌] K.Ogura: "Formation of a Stable and Catalytically Active Complex of the Two Essential Components of Hexaprenyl Diphoshphate synthese from Micrococcus luteus B-P26" Biochem.Biophys.Res.Commun.160. 448-452 (1989)
[文献書誌] K.Ogura: "Undecaprenyl Diphoshate Synthase Reaction with Artificial Substrate Homelogues---Novel Behavior in the Termination of Prenyl Chain Elongation" Tetrahedron. 45. 6145-6160 (1989)
[文献書誌] K.Ogura: "Kinetic Studies on th Prenyl Chain Elongation by Undecaprenyl Diphosphate Synthase with Artificial Substrate Homologues" FEBS Let.257. 71-74 (1989)
[文献書誌] S.Nozoe: "Chirospecific Synthesis of Amino Acids and Analogues" Amino Acids.
[文献書誌] S.Nozoe: "Synthesis of (3S,5R)-Carbapenam-3-carboxylate" J.Chem.soe.,chem.Commun.
[文献書誌] Y.Maki: "N-acylation of stimulatory amino acids changes chiral recognition of the flesh fly labellar sugar site" J.compt.Physiol.,A. 165. 193-196 (1989)
[文献書誌] Y.Maki: "Farnesyl Diphosphate Synthetase Reaction of Articifial Substrates with Oxygen" Chemistry Letters.
[文献書誌] H.Kakisawa: "Absolute Configuration of Marine Diterpenes Possessing a Xenicane Skeleton" Tetrahedron Letters. 30. 3147-3150 (1989)
[文献書誌] H.Kakisawa: "The Absolute Configuration at 8- and 9-Carbons of Adda, an Amino Acid Component of Hepatotoxin,Cyanoviridin RR" Tetrahedron Letters. 30. 4245-4248 (1989)
[文献書誌] U.Sankawa: "Nonstereospecific Proton Removal in the Enzymatic Formation of Orsellinic Acid from Chiral Malonate" J.Am.Chem.Soc.111. 5498-5500 (1989)
[文献書誌] A.Kawaguchi: "Binding site of Cerulenin in fatty acid synthetase" J.Biochem.105. 751-755 (1989)
[文献書誌] Y.Shizuri: "Potasium Lespedezate and Potassium Isolespedezate,Bioactive Substances concerned with Circadian Rhythem in Nyctinastic Plants" Tetrahedron Letters. 30. 3991-3994 (1989)
[文献書誌] Y.Shizuri: "Total Syntheses of Potassium Lespedezate and Potassium Isolespedezate,Bioactive Substances Concerned with Circadian Rhythm in Nyctinastic Plants" Tetrahedron Letters. 30. 6389-6392 (1989)
[文献書誌] Y.Shizuri: "Bioactive Substances from Lespedeza Cuneata L.G.Don and Their Biological Activities" Tetrahedron. 46. 383-394 (1990)
[文献書誌] D.Uemura: "Structure-Activity Studies of the Nonphorbol Tumor Promoter Palytoxin in Swiss 3T3 Cells" Cancer Res.49. 5837-5842 (1989)
[文献書誌] T.Goto: "Structure of Anthocyanins in Scarlet,Purple, and Blue Flowers of Salvia" Tetrahedron Lettrs. 30. 6729-6732 (1989)
[文献書誌] T.Goto: "Structure of Lobel-nin A and B,Novel Anthocyanins Acylated with Three and Four Different Organic Acids,Respectively" Tetrahedron Lettrs. 30. 6055-6058 (1989)
[文献書誌] T.Goto: "Structure of Malonylshisonin,a Genuine Pigment in Purple Leaves of Perilla ocimoides L.var.crispa Benth" Agric.Biol.Chem.53. 797-800 (1989)
[文献書誌] H.Niwa: "An Efficient Enantioselective Synthesis of(+)-Indicine N-Oxide,an Antitumor Pyrrolizidine Alkaloid" Tetrahedron Letters. 30. 4985-4986 (1989)
[文献書誌] K.Fuji: "Chiral Total Synthesis of Indole Alkaloids of the Aspidosperma and Hunteria Types" J.Org.Chem.55. 517-521 (1990)
[文献書誌] T.Tokoroyama: "Synthetic Studies on Terpenoid compounds Part 27.Total Synthesis of Calodendrolide" J.Chem.Soc.,Chem.Commun.
[文献書誌] T.Tokuyama: "Alkaloids from Dendrobatid Poison Frogs:Further(allo)-pumiliotoxins and a Ressignment of the Keto Function in Pumiliotoxin 307F" Tetrahedron.
[文献書誌] T.Suga: "Glycinoprenols:Novel Polyprenols Possessing a.Phythyl Residue from the Leaves of Soybean" J.Org.chem. 54. 3390-3393 (1989)
[文献書誌] T.Suga: "Sesquiterpene Glycosides and other Terpene Constituents from the Flowers of Pittosporum Tobira" Phytochemistry. 28. 3085-3091 (1989)
[文献書誌] T.Suga: "Synthesis of 4- and 5-Regioselectively Deuterated Geranyl Diphosphates" J.Chem.Soc.,Perkin Trans.l. 1811-1814 (1989)
[文献書誌] S.Ito: "Azaclaisen Rearrangement of Amide Enolates.Stereoselective Syntheses of 2,3-Disubstituted Carboxamides" Tetrahedron Letters. 31. 727-730 (1990)
[文献書誌] S.Ito: "An Efficient Method for Hydrolysis of N-Monosubstituted Amides via Acetoxypivalimides." Tetrahedron Letters. 31. 731-734 (1990)
[文献書誌] S.Ito: "A few new Method for Asymmetric Synthesis" Pure and Appl.Chem.
[文献書誌] T.Katsuki: "Stereoelectronically Controlled[2,3]Witting Rearrangement of Isopropyl 2'-Heterosubstituted 2'-Alkenyloxyacetates" Tetrahedron Letters.

1989 年度 実績報告書

生体機能物質の生合成機構とその応用に関する研究

研究代表者

村井 章夫 北海道大学, 理学部, 教授 (20000838)

研究成果

[文献書誌] M.Takasugi: "Brassicanals A and B,Novel Sulfur-containing Phytoalexins from the Chinese Cabbage Brassica compestris L.ssp.pekinensis" Chemistry Letters. 209-210 (1990)

[文献書誌] M.Takasugi: "4-Methoxybrassinin,a Sulfur-containing Phytoalexin from Brassica oleraces" Phytochemistry.

[文献書誌] K.Ogura: "Protection of Hexaprenyl Diphosphate Synthase of Micrococcus luteus B-P 26 against Inactivation by Sulphydryl Reagents and Arginine-specific Reagents" Biochem.Biophys.Acta. 995. 138-143 (1989)

[文献書誌] K.Ogura: "The Biosynthesis of Dehydrolichyl Phosphates by Rat Liver Microsomes" Biochem.Biophys.Acta. 1002. 218-224 (1989)

[文献書誌] K.Ogura: "Artificially Elicited Capabilities of Enzymes and Their Application in Natural Product Chemistry" Pure Apple.Chem.61. 477-480 (1989)

[文献書誌] K.Ogura: "Formation of a Stable and Catalytically Active Complex of the Two Essential Components of Hexaprenyl Diphoshphate synthese from Micrococcus luteus B-P26" Biochem.Biophys.Res.Commun.160. 448-452 (1989)

[文献書誌] K.Ogura: "Undecaprenyl Diphoshate Synthase Reaction with Artificial Substrate Homelogues---Novel Behavior in the Termination of Prenyl Chain Elongation" Tetrahedron. 45. 6145-6160 (1989)

[文献書誌] K.Ogura: "Kinetic Studies on th Prenyl Chain Elongation by Undecaprenyl Diphosphate Synthase with Artificial Substrate Homologues" FEBS Let.257. 71-74 (1989)

[文献書誌] S.Nozoe: "Chirospecific Synthesis of Amino Acids and Analogues" Amino Acids.

[文献書誌] S.Nozoe: "Synthesis of (3S,5R)-Carbapenam-3-carboxylate" J.Chem.soe.,chem.Commun.

[文献書誌] Y.Maki: "N-acylation of stimulatory amino acids changes chiral recognition of the flesh fly labellar sugar site" J.compt.Physiol.,A. 165. 193-196 (1989)

[文献書誌] Y.Maki: "Farnesyl Diphosphate Synthetase Reaction of Articifial Substrates with Oxygen" Chemistry Letters.

[文献書誌] H.Kakisawa: "Absolute Configuration of Marine Diterpenes Possessing a Xenicane Skeleton" Tetrahedron Letters. 30. 3147-3150 (1989)

[文献書誌] H.Kakisawa: "The Absolute Configuration at 8- and 9-Carbons of Adda, an Amino Acid Component of Hepatotoxin,Cyanoviridin RR" Tetrahedron Letters. 30. 4245-4248 (1989)

[文献書誌] U.Sankawa: "Nonstereospecific Proton Removal in the Enzymatic Formation of Orsellinic Acid from Chiral Malonate" J.Am.Chem.Soc.111. 5498-5500 (1989)

[文献書誌] A.Kawaguchi: "Binding site of Cerulenin in fatty acid synthetase" J.Biochem.105. 751-755 (1989)

[文献書誌] Y.Shizuri: "Potasium Lespedezate and Potassium Isolespedezate,Bioactive Substances concerned with Circadian Rhythem in Nyctinastic Plants" Tetrahedron Letters. 30. 3991-3994 (1989)

[文献書誌] Y.Shizuri: "Total Syntheses of Potassium Lespedezate and Potassium Isolespedezate,Bioactive Substances Concerned with Circadian Rhythm in Nyctinastic Plants" Tetrahedron Letters. 30. 6389-6392 (1989)

[文献書誌] Y.Shizuri: "Bioactive Substances from Lespedeza Cuneata L.G.Don and Their Biological Activities" Tetrahedron. 46. 383-394 (1990)

[文献書誌] D.Uemura: "Structure-Activity Studies of the Nonphorbol Tumor Promoter Palytoxin in Swiss 3T3 Cells" Cancer Res.49. 5837-5842 (1989)

[文献書誌] T.Goto: "Structure of Anthocyanins in Scarlet,Purple, and Blue Flowers of Salvia" Tetrahedron Lettrs. 30. 6729-6732 (1989)

[文献書誌] T.Goto: "Structure of Lobel-nin A and B,Novel Anthocyanins Acylated with Three and Four Different Organic Acids,Respectively" Tetrahedron Lettrs. 30. 6055-6058 (1989)

[文献書誌] T.Goto: "Structure of Malonylshisonin,a Genuine Pigment in Purple Leaves of Perilla ocimoides L.var.crispa Benth" Agric.Biol.Chem.53. 797-800 (1989)

[文献書誌] H.Niwa: "An Efficient Enantioselective Synthesis of(+)-Indicine N-Oxide,an Antitumor Pyrrolizidine Alkaloid" Tetrahedron Letters. 30. 4985-4986 (1989)

[文献書誌] K.Fuji: "Chiral Total Synthesis of Indole Alkaloids of the Aspidosperma and Hunteria Types" J.Org.Chem.55. 517-521 (1990)

[文献書誌] T.Tokoroyama: "Synthetic Studies on Terpenoid compounds Part 27.Total Synthesis of Calodendrolide" J.Chem.Soc.,Chem.Commun.

[文献書誌] T.Tokuyama: "Alkaloids from Dendrobatid Poison Frogs:Further(allo)-pumiliotoxins and a Ressignment of the Keto Function in Pumiliotoxin 307F" Tetrahedron.

[文献書誌] T.Suga: "Glycinoprenols:Novel Polyprenols Possessing a.Phythyl Residue from the Leaves of Soybean" J.Org.chem. 54. 3390-3393 (1989)

[文献書誌] T.Suga: "Sesquiterpene Glycosides and other Terpene Constituents from the Flowers of Pittosporum Tobira" Phytochemistry. 28. 3085-3091 (1989)

[文献書誌] T.Suga: "Synthesis of 4- and 5-Regioselectively Deuterated Geranyl Diphosphates" J.Chem.Soc.,Perkin Trans.l. 1811-1814 (1989)

[文献書誌] S.Ito: "Azaclaisen Rearrangement of Amide Enolates.Stereoselective Syntheses of 2,3-Disubstituted Carboxamides" Tetrahedron Letters. 31. 727-730 (1990)

[文献書誌] S.Ito: "An Efficient Method for Hydrolysis of N-Monosubstituted Amides via Acetoxypivalimides." Tetrahedron Letters. 31. 731-734 (1990)

[文献書誌] S.Ito: "A few new Method for Asymmetric Synthesis" Pure and Appl.Chem.

[文献書誌] T.Katsuki: "Stereoelectronically Controlled[2,3]Witting Rearrangement of Isopropyl 2'-Heterosubstituted 2'-Alkenyloxyacetates" Tetrahedron Letters.

1989 年度実績報告書

村井章夫北海道大学, 理学部, 教授 (20000838)