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2003 Fiscal Year Final Research Report Summary

Study of the Reaction of Unprotected Amino Acids in Aqueous Media and its Application for the Short-Step Synthesis of Ergot Alkaloids

Research Project

Project/Area Number 13672237
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionToho University

Principal Investigator

YOKOYAMA Yuusaku  Toho University, Department of Pharmaceutical Sciences, Associate Professor, 薬学部, 助教授 (10095325)

Project Period (FY) 2001 – 2003
KeywordsBemztrvptophan / Amino acids / Bromination / Racemization / N-Methvlamino acids / Protecting groups / Aqueous media / Tryptophan
Research Abstract

1)Several free amino acids, phrnylglycine, phenylalanine, tryptophan were heated at 100-130℃ under alkaline or acidic condition in water or various polar organic solvents.Although serious racemization and decomposition occurred in polar organic solvents such as DMF, DMSO, or ethylene glycol under alkaline condition (K_2CO_3, KOH, Et_3N), those phenomenon did not occur, or were largely decreased in water or water containing organic solvent under the same alkaline condition.
2)Bromination of unprotected phenylalanine with bromoisocyanuric acid sodium salt in strong acidic solution (60% H_2SO_4) gave the mixture of 2-bromo-and 4-bromophenylalanine in 31% and 58% yield, respectively.
3)The reaction of benz[e]-, benz[f]-, benz[g] indoles with dl-serine in the presence of Ac_2O in AcOH at 50-60℃ gave the corresponding dl-N-acetylbenztryptophanes in 42-59% yield accompanied with 2,3-di-subusituted derivatives as by-products. Kinetic resolution of the above dl-N-acetylbenztryptophans by Aspergillus acylase gave corresponding optically pure(S)-benztryptophans.

  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] Yuusaku Yokoyama: "Does Water Suppress the Racemization and Decomposition of Amino Acids?"J.Chem.Soc.,Perkin Trans.1. 1431-1434 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yuusaku Yokoyama: "N-Boc-4-Bromo-N-methyl-1 -tosyl-D-tryptophan Methyl Ester, A Key Intermediate In the Synthesis of Optically Active Ergot Alkaloids"Heterocycles. 55(4). 653-659 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yuusaku Yokoyama: "Synthetic Studies on Indoles and Related Compounds 50.Improved Synthesis of 7,9-Didecarboxymethoxthine"Heterocycles. 56. 515-518 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yuusaku Yokoyama: "A Study for Palladium-Catalyzed Chemoselective Vinylation at C-3 Position of 4-Bromo-1-Tosylindole."Heterocycles. 56. 525-529 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yuusaku Yokoyama: "Total Synthesis without Protection : Three-Step Synthesis of Optically Active Clavicipitic Acids by a Biomimetic Route"Eur.J.Org.Chem.. 1244-1253 (2004)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 横山 祐作: "保護基を用いない有機合成"ファルマシア. 39(12). 1163-1167 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Somei M, Yokoyama Y, Murakami Y, Ninomiya I, Kiguchi T: "Recent Synthetic Studies of the Ergot Alkaloids and Related Compounds."The Alkaloids Ed. (Cordell D.A.). 35. 193-253 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hikawa H, Yokoyama Y, Murakami Y: "A Short Synthesis of Optically Active γ,γ-Dimethylallyltryptophan (DMAT)."Synthesis. 214-216 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yokoyama Y, Osanai K, Mitsuhashi M, Kondo K, Murakami Y: "An Efficient Method of Synthesizing Optically Pure N-Boc-4-bromo-N-methyl-1-tosyl-D-tryptophan methyl Ester, A Key Intermediate in the Synthesis of Optically Active Ergot Alkaloids."Heterocycles. 55. 653-659 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yokoyama Y, Hi kawa H, Murakami Y: "Does Water Suppress the racemization and Decomposition of Amino Acids?"J.Chem.Soc., Perkin Trans. 1. 1432-1434 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yokoyama Y, Tsuruta K, Murakami Y: "A Study for Palladium-Catalyzed Chemoselective Vinylation at C-5 Position of 4-Bromo-1-tosylindoles"Heterocycles. 56. 525-529 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yokoyama Y, Hikawa H, Mitsuhashi M, Uyama A, Hiroki H, Murakami Y: "Total Synthesis without Protection: Three-Step Synthesis of Optically Active Clavicipitic Acids via a Biomimetic Route"Eur.J.Org.Chem.. 1244-1253 (2004)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2005-04-19  

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