1989 Fiscal Year Annual Research Report

生体機能物質の生合成機構とその応用に関する研究

Research Project

Project/Area Number	63303003
Research Institution	Hokkaido University
Principal Investigator	村井章夫北海道大学, 理学部, 教授 (20000838)
Co-Investigator(Kenkyū-buntansha)	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)
Keywords	グリシノエクレピンA / 生合成 / 生合成推定経路
Research Abstract	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)。

Research Products
(34 results)

All Other

All Publications (34 results)

[Publications] M.Takasugi: "Brassicanals A and B,Novel Sulfur-containing Phytoalexins from the Chinese Cabbage Brassica compestris L.ssp.pekinensis" Chemistry Letters. 209-210 (1990)
[Publications] M.Takasugi: "4-Methoxybrassinin,a Sulfur-containing Phytoalexin from Brassica oleraces" Phytochemistry.
[Publications] 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)
[Publications] K.Ogura: "The Biosynthesis of Dehydrolichyl Phosphates by Rat Liver Microsomes" Biochem.Biophys.Acta. 1002. 218-224 (1989)
[Publications] K.Ogura: "Artificially Elicited Capabilities of Enzymes and Their Application in Natural Product Chemistry" Pure Apple.Chem.61. 477-480 (1989)
[Publications] 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)
[Publications] K.Ogura: "Undecaprenyl Diphoshate Synthase Reaction with Artificial Substrate Homelogues---Novel Behavior in the Termination of Prenyl Chain Elongation" Tetrahedron. 45. 6145-6160 (1989)
[Publications] K.Ogura: "Kinetic Studies on th Prenyl Chain Elongation by Undecaprenyl Diphosphate Synthase with Artificial Substrate Homologues" FEBS Let.257. 71-74 (1989)
[Publications] S.Nozoe: "Chirospecific Synthesis of Amino Acids and Analogues" Amino Acids.
[Publications] S.Nozoe: "Synthesis of (3S,5R)-Carbapenam-3-carboxylate" J.Chem.soe.,chem.Commun.
[Publications] 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)
[Publications] Y.Maki: "Farnesyl Diphosphate Synthetase Reaction of Articifial Substrates with Oxygen" Chemistry Letters.
[Publications] H.Kakisawa: "Absolute Configuration of Marine Diterpenes Possessing a Xenicane Skeleton" Tetrahedron Letters. 30. 3147-3150 (1989)
[Publications] 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)
[Publications] U.Sankawa: "Nonstereospecific Proton Removal in the Enzymatic Formation of Orsellinic Acid from Chiral Malonate" J.Am.Chem.Soc.111. 5498-5500 (1989)
[Publications] A.Kawaguchi: "Binding site of Cerulenin in fatty acid synthetase" J.Biochem.105. 751-755 (1989)
[Publications] Y.Shizuri: "Potasium Lespedezate and Potassium Isolespedezate,Bioactive Substances concerned with Circadian Rhythem in Nyctinastic Plants" Tetrahedron Letters. 30. 3991-3994 (1989)
[Publications] 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)
[Publications] Y.Shizuri: "Bioactive Substances from Lespedeza Cuneata L.G.Don and Their Biological Activities" Tetrahedron. 46. 383-394 (1990)
[Publications] D.Uemura: "Structure-Activity Studies of the Nonphorbol Tumor Promoter Palytoxin in Swiss 3T3 Cells" Cancer Res.49. 5837-5842 (1989)
[Publications] T.Goto: "Structure of Anthocyanins in Scarlet,Purple, and Blue Flowers of Salvia" Tetrahedron Lettrs. 30. 6729-6732 (1989)
[Publications] 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)
[Publications] 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)
[Publications] H.Niwa: "An Efficient Enantioselective Synthesis of(+)-Indicine N-Oxide,an Antitumor Pyrrolizidine Alkaloid" Tetrahedron Letters. 30. 4985-4986 (1989)
[Publications] K.Fuji: "Chiral Total Synthesis of Indole Alkaloids of the Aspidosperma and Hunteria Types" J.Org.Chem.55. 517-521 (1990)
[Publications] T.Tokoroyama: "Synthetic Studies on Terpenoid compounds Part 27.Total Synthesis of Calodendrolide" J.Chem.Soc.,Chem.Commun.
[Publications] T.Tokuyama: "Alkaloids from Dendrobatid Poison Frogs:Further(allo)-pumiliotoxins and a Ressignment of the Keto Function in Pumiliotoxin 307F" Tetrahedron.
[Publications] T.Suga: "Glycinoprenols:Novel Polyprenols Possessing a.Phythyl Residue from the Leaves of Soybean" J.Org.chem. 54. 3390-3393 (1989)
[Publications] T.Suga: "Sesquiterpene Glycosides and other Terpene Constituents from the Flowers of Pittosporum Tobira" Phytochemistry. 28. 3085-3091 (1989)
[Publications] T.Suga: "Synthesis of 4- and 5-Regioselectively Deuterated Geranyl Diphosphates" J.Chem.Soc.,Perkin Trans.l. 1811-1814 (1989)
[Publications] S.Ito: "Azaclaisen Rearrangement of Amide Enolates.Stereoselective Syntheses of 2,3-Disubstituted Carboxamides" Tetrahedron Letters. 31. 727-730 (1990)
[Publications] S.Ito: "An Efficient Method for Hydrolysis of N-Monosubstituted Amides via Acetoxypivalimides." Tetrahedron Letters. 31. 731-734 (1990)
[Publications] S.Ito: "A few new Method for Asymmetric Synthesis" Pure and Appl.Chem.
[Publications] T.Katsuki: "Stereoelectronically Controlled[2,3]Witting Rearrangement of Isopropyl 2'-Heterosubstituted 2'-Alkenyloxyacetates" Tetrahedron Letters.

1989 Fiscal Year Annual Research Report

生体機能物質の生合成機構とその応用に関する研究

Principal Investigator

村井 章夫 北海道大学, 理学部, 教授 (20000838)

Research Products

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

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

[Publications] 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)

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

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

[Publications] 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)

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

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

[Publications] S.Nozoe: "Chirospecific Synthesis of Amino Acids and Analogues" Amino Acids.

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

[Publications] 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)

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

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

[Publications] 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)

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

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

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

[Publications] 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)

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

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

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

[Publications] 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)

[Publications] 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)

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

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

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

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

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

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

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

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

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

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

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

村井章夫北海道大学, 理学部, 教授 (20000838)