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Part I. Studies directed towards the asymmetric synthesis of amipurimycin. Part II. The development of novel peptide-based nucleic acid surrogates

Yoo, Ji Uk
http://rave.ohiolink.edu/etdc/view?acc_num=case1061231832

Abstract Details

1994, Doctor of Philosophy, Case Western Reserve University, Chemistry.
Part I. Studies directed towards the asymmetric synthesis of amipurimycin. A stereocontrolled approach to the antifungal antibiotic, amipurimycin, is described. Stereodivergent synthesis of erythro- and threo-6-amino-6-deoxyheptoulose derivatives via an optically active oxazolidine aldehyde has been optimized. Also, the stereo- and regiocontrolled synthesis of pyranosyl 2-aminopurine nucleosides is described. Coupling of bissilylated N2-acetyl-2-aminopurine with peracetylated glucopyranosides afforded good yields of the corresponding N9-β-2-aminopurine nucleosides. Glycosylation of N2-acetyl-2-amino-6-chloropurine could be made to produce either N9- or N7-nucleosides selectively and these were converted to their respective 2-aminopurine nucleosides by transfer hydrogenolysis. Various nucleosidation protocols were applied to the carbohydrate portion of amipurimycin, but the resulting nucleosides did not correlate with an authentic sample. Part II. The development of novel peptide-based nucleic and surrogates. Peptide-based nucleic acid surrogates incorporating Ser(CH2B)-Gly subunits were designed and synthesized. BOC-Ser(MTM)-OMe was prepared from serine and used for the coupling with silylated thymine to give acyclic nu cleosides. This methodology has been applied to the synthesis of three other natural nucleobases (A, G, & C) as well. It was further demonstrated that such units may be linked together using standard peptide coupling techniques without racemization or β-elimination
Philip Garner (Advisor)
225 p.
Chemistry, Organic
Asymmetric synthesis; Amipurimycin; Peptide-based nucleic acid

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Citations

  • Yoo, J. U. (1994). Part I. Studies directed towards the asymmetric synthesis of amipurimycin. Part II. The development of novel peptide-based nucleic acid surrogates [Doctoral dissertation, Case Western Reserve University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=case1061231832

    APA Style (7th edition)

  • Yoo, Ji. Part I. Studies directed towards the asymmetric synthesis of amipurimycin. Part II. The development of novel peptide-based nucleic acid surrogates. 1994. Case Western Reserve University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=case1061231832.

    MLA Style (8th edition)

  • Yoo, Ji. "Part I. Studies directed towards the asymmetric synthesis of amipurimycin. Part II. The development of novel peptide-based nucleic acid surrogates." Doctoral dissertation, Case Western Reserve University, 1994. http://rave.ohiolink.edu/etdc/view?acc_num=case1061231832

    Chicago Manual of Style (17th edition)

case1061231832
552
© 1994, all rights reserved.
This open access ETD is published by Case Western Reserve University School of Graduate Studies and OhioLINK.