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Total Synthesis of Natural Products with Antimicrobial Activity

  • Book
  • © 2018

Overview

Authors:
  1. Andrew Giltrap

    1. School of Chemistry, The University of Sydney, Sydney, Australia

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  • 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
  • Describes the total synthesis of two antimicrobial non-ribosomal peptides (NRPs) classes: teixobactin and skyllamycins
  • Demonstrates how synthetic NRPs’ natural products can be used to inhibit the growth of biofilms and combat bacterial pathogens

Part of the book series: Springer Theses (Springer Theses)

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Table of contents (5 chapters)

  1. Front Matter

    Pages i-xxiv
    Download chapter PDF

  2. Introduction

    • Andrew Giltrap
    Pages 1-31

  3. Total Synthesis of Teixobactin

    • Andrew Giltrap
    Pages 33-69

  4. Synthesis of Deshydroxy Skyllamycins A–C

    • Andrew Giltrap
    Pages 71-117

  5. Total Synthesis of Skyllamycins A–C

    • Andrew Giltrap
    Pages 119-150

  6. Experimental

    • Andrew Giltrap
    Pages 151-223

  7. Back Matter

    Pages 225-268
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Keywords

About this book

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.

Authors and Affiliations

  • School of Chemistry, The University of Sydney, Sydney, Australia

    Andrew Giltrap

About the author

Andrew M. Giltrap was raised in Sydney, Australia and carried out his Bachelor of Science majoring in chemistry at the University of Sydney. During this time, Andrew undertook his final year undergraduate research project under the supervision of Professor Richard J. Payne, receiving the University Medal for undergraduate excellence. Andrew continued in the laboratory of Professor Payne, commencing his PhD studies in 2013 funded by an Australian Postgraduate Award, the Sydney University Vice-Chancellor’s Research Scholarship and the John A. Lamberton Scholarship. During his PhD, Andrew’s research focused on the total synthesis of antimicrobial peptide natural products, notably completing the first total syntheses of teixobactin and skyllamycins A-C. He is currently a postdoctoral research associate at the University of Sydney.

Bibliographic Information

  • Book Title: Total Synthesis of Natural Products with Antimicrobial Activity

  • Authors: Andrew Giltrap

  • Series Title: Springer Theses

  • DOI: https://doi.org/10.1007/978-981-10-8806-3

  • Publisher: Springer Singapore

  • eBook Packages: Chemistry and Materials Science, Chemistry and Material Science (R0)

  • Copyright Information: Springer Nature Singapore Pte Ltd. 2018

  • Hardcover ISBN: 978-981-10-8805-6Published: 14 May 2018

  • Softcover ISBN: 978-981-13-4245-5Published: 14 February 2019

  • eBook ISBN: 978-981-10-8806-3Published: 02 May 2018

  • Series ISSN: 2190-5053

  • Series E-ISSN: 2190-5061

  • Edition Number: 1

  • Number of Pages: XXIV, 268

  • Number of Illustrations: 85 b/w illustrations, 59 illustrations in colour

  • Topics: Medicinal Chemistry, Medical Biochemistry, Drug Resistance

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