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Synlett 2022; 33(17): 1695-1706
DOI: 10.1055/a-1885-4934
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A Decade of Research on Daptomycin

Scott D. Taylor
I am grateful to The Natural Sciences and Engineering Research Council of Canada (RGPIN 2012-155283 and RGPIN-2017-04233) and the Canadian Institutes for Health Research (398954-2011) for funding this research.
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Abstract

Daptomycin is a calcium-dependent cyclic lipodepsipeptide antibiotic that is used in the clinic for treating serious infections caused by Gram-positive bacteria. In this account, I present a summary of the research that has been conducted in my group on daptomycin’s total chemical synthesis, its structure–activity relationships, and its mechanism of action, since we began our studies a decade ago.

1 Introduction

2 Solid-Phase Synthesis of Daptomycin by an On-Resin Cyclization

3 α-Azido Acids and Alternative Routes to Daptomycin by On-Resin Cyclization

4 Synthesis of Daptomycin by an Off-Resin Cyclization

5 SAR Studies on Daptomycin

6 Oligomerization of Daptomycin on Membranes

7 The Chiral Target of Daptomycin

8 SAR Studies on Phosphatidylglycerol

9 Conclusions

Key words

antibiotics - daptomycin - solid-phase synthesis - mechanism - structure–activity relationships


Publication History

Received: 07 June 2022

Accepted: 27 June 2022

Accepted Manuscript online:
27 June 2022

Article published online:
29 July 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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