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Total Synthesis of Natural Products with Antimicrobial Activity

  • Andrew Giltrap

Part of the Springer Theses book series (Springer Theses)

Table of contents

  1. Front Matter
    Pages i-xxiv
  2. Andrew Giltrap
    Pages 1-31
  3. Andrew Giltrap
    Pages 33-69
  4. Andrew Giltrap
    Pages 71-117
  5. Andrew Giltrap
    Pages 119-150
  6. Andrew Giltrap
    Pages 151-223
  7. Back Matter
    Pages 225-268

About this book

Introduction

This thesis focuses on the development of efficient and scalable total syntheses of natural products that can be used as preferred scaffolds for anti-infective drug discovery. It describes the total synthesis of two classes of antimicrobial non-ribosomal peptides (NRPs) – teixobactin and the skyllamycins – with subsequent biological evaluation. The first part describes the first total synthesis of teixobactin by means of a solid-phase peptide synthesis-macrolactamisation approach, yielding a synthetic natural product that can combat a number of clinically relevant Gram-positive bacterial pathogens. The second part describes the first total synthesis of skyllamycins A-C, a family of structurally complex cyclic NRPs, which inhibit the growth of the Pseudomonas aeruginosa biofilms that are responsible for significant mortality among cystic fibrosis patients.

Keywords

Non-Ribosomal Peptides (NRPs) Total Synthesis Teixobactin Skyllamycins A-C Proteinogenic Amino Acids Antimicrobial Resistance Deshydroxy Skyllamycin Gram-positive Bacterial Pathogens α-OH-Gly Pseudomonas aeruginosa Biofilms

Authors and affiliations

  • Andrew Giltrap
    • 1
  1. 1.School of ChemistryThe University of SydneySydneyAustralia

Bibliographic information

  • DOI https://doi.org/10.1007/978-981-10-8806-3
  • Copyright Information Springer Nature Singapore Pte Ltd. 2018
  • Publisher Name Springer, Singapore
  • eBook Packages Chemistry and Materials Science
  • Print ISBN 978-981-10-8805-6
  • Online ISBN 978-981-10-8806-3
  • Series Print ISSN 2190-5053
  • Series Online ISSN 2190-5061
  • Buy this book on publisher's site