Synthesis and Absolute Configuration of Wybutine, the Fluorescent Minor Base from Phenylalanine Transfer Ribonucleic Acids

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概要

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• The phosphonium chloride 6 having an optically active amino acid moiety was synthesized from (S)-serine benzylester tosylate (2b) through a six-step route. The utility of 6 as a reagent for the Witting reaction was exemplified in the olefination with benzaldehyde, affording the (E)-β, γ-unsaturated amino acid derivative 11 as a sole geometrical ispmer. This new method of amino acid homologation was successuflly employed for the first chiral synthesis of wybutine (1c), the minor base isolated from yeast phenylalanine transfer ribonucleic acids : the Wittig reaction between 6 and the tricyclic aldehyde 16 followed successively by methylation and catalytic reduction afforded 1c. Comparison of wybutine with synthetic 1c has unequivocally established that wybutine has an S configuration.

• 公益社団法人日本薬学会の論文
• 1991-06-25

著者

• 飯田 剛彦

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 板谷 泰助

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 板谷 泰助

  金沢大学薬学部

• 水谷 朱見

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 水谷 朱見

  Faculty Of Pharmaceutical Sciences Kanazawa University

関連論文

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• Purines. LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides
• Purines. LXVIII. Trifluoroperoxyacetic Acid Oxidation of N^6-Benzyladenine : Formation of the N(3)-Oxide and N(7)-Oxide, and Their Cytokinin Activities
• Purines. LXVII. An Alternative Synthesis of Adenine 7-Oxide : N-Oxidation of the Adenine Ring Utilizing Blocking/Deblocking at the 1-Position
• Purines. LXVI. Adenine 7-Oxide : Its Synthesis, Chemical Properties, and X-ray Molecular Structure
• Purines. LII. Synthesis and Biological Evaluation of 8-Methylguanine 7-Oxide and Its 9-Arylmethyl Derivatives
• Purines. LI. Synthesis and Biological Activity of Hypoxanthine 7-N-Oxide and Related Compounds
• Purines. L. Synthesis and Antileukemic Activity of the Antibiotic Guanine 7-Oxide and Its 9-Substituted Derivatives
• FORMATION OF CYCLIC CARBONATES IN THE REACTIONS OF 1,2-GLYCOLS WITH OXALYL CHLORIDE
• Purines. XXI. Synthesis of Adenine 1-Oxides Carrying an Allylic Side Chain at the 9-Position
• Synthesis of 3-β-D-Ribofuranosylwye, the Most Probable Structure for Wyosine from Torulopsis utilis Phenylalanine Transfer Ribonucleic Acid
• Synthesis of 5-(Methylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide, a Synthetic Intermediate for 3-Methyl-9-β-D-ribofuranosylpurines
• An Improved Procedure for the Synthesis of 1-Alkyl-5-(alkylamino)-imidazole-4-carboxamides, Synthetic Intermediates for 3,9-Dialkylpurine Derivatives
• Synthesis of N, N, 3,9-Tetraalkyladeninium Halides by Alkylations of N, N, 3- and N, N, 9-Trialkyladenines
• Purines. XXXV. : Synthesis and Cytokinin Activity of Racemic 1'-Methylzeatin
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• Wittig Reaction with N-Protected 3-(Triphenylphosphonio)alaninates : Synthesis of Optically Active (E)-(2-Arylvinyl)glycine Derivatives
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• Purines. XX. Synthesis of 1-Substituted 5-Aminoimidazole-4-carboxamidines and Related Compounds
• Syntheses of N, N, 3- and N, N, 9-Trialkyladenines by Alkylation of N, N-Dialkyladenines
• Studies towards the Synthesis of the Fluorescent Bases of Phenylalanine Transfer Ribonucleic Acids : Synthesis of 7-Methylwye Isolated from Extremely Thermophilic Archaebacteria
• Ind. -N-Alkylation of Tryptophan and Synthesis of 1-Alkyltryptophan Hydrazides
• フェニルアラニン転移リボ核酸超修飾ヌクレオシドの合成をめぐって
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• Syntheses of Optically Active, Protected and Unprotected Vinylglycines
• 3-Methylisoguanosine : Synthesis and Acidic Hydrolysis of the Glycosyl Bond
• Synthesis of 7-Methyl-3-β-D-ribofuranosylwye, the Putative Structure for the Hypermodified Nucleoside Isolated from Archaebacterial Transfer Ribonucleic Acids
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