dc.contributor.author |
Hanna, Cameron C |
|
dc.contributor.author |
Hermant, Yann O |
|
dc.contributor.author |
Harris, Paul WR |
|
dc.contributor.author |
Brimble, Margaret A |
|
dc.coverage.spatial |
United States |
|
dc.date.accessioned |
2023-03-09T04:19:37Z |
|
dc.date.available |
2023-03-09T04:19:37Z |
|
dc.date.issued |
2021-04 |
|
dc.identifier.citation |
(2021). Accounts of Chemical Research, 54(8), 1878-1890. |
|
dc.identifier.issn |
0001-4842 |
|
dc.identifier.uri |
https://hdl.handle.net/2292/63247 |
|
dc.description.abstract |
The rise of multidrug resistant bacteria has significantly compromised our supply of antibiotics and poses an alarming medical and economic threat to society. To combat this problem, it is imperative that new antibiotics and treatment modalities be developed, especially those toward which bacteria are less capable of developing resistance. Peptide natural products stand as promising candidates to meet this need as bacterial resistance is typically slow in response to their unique modes of action. They also have additional benefits including favorable modulation of host immune responses and often possess broad-spectrum activity against notoriously treatment resistant bacterial biofilms. Moreover, nature has provided a wealth of peptide-based natural products from a range of sources, including bacteria and fungi, which can be hijacked in order to combat more dangerous clinically relevant infections.This Account highlights recent advances in the total synthesis and development of a range of peptide-based natural product antibiotics and details the medicinal chemistry approaches used to optimize their activity.In the context of antibiotics with potential to treat Gram-positive bacterial infections, this Account covers the synthesis and optimization of the natural products daptomycin, glycocin F, and alamethicin. In particular, the reported synthesis of daptomycin highlights the utility of on-resin ozonolysis for accessing a key kynurenine residue from the canonical amino acid tryptophan. Furthermore, the investigation into glycocin F analogues uncovered a potent lead compound against <i>Lactobacillus plantarum</i> that bears a non-native thioacetal linkage to a <i>N-</i>acetyl-d-glucosamine (GlcNAc) sugar, which is otherwise <i>O</i>-linked in its native form.For mycobacterial infections, this Account covers the synthesis and optimization of teixobactin, callyaerin A, lassomycin, and trichoderin A. The synthesis of callyaerin A, in particular, highlighted the importance of a (<i>Z</i>)-2,3-diaminoacrylamide motif for antimicrobial activity against <i>Mycobacterium tuberculosis</i>, while the synthesis of trichoderin A highlighted the importance of (<i>R</i>)-stereoconfiguration in a key 2-amino-6-hydroxy-4-methyl-8-oxodecanoic acid (AHMOD) residue.Lastly, this Account covers lipopeptide antibiotics bearing activity toward Gram-negative bacterial infections, namely, battacin and paenipeptin C. In both cases, optimization of the N-terminal lipid tails led to the identification of analogues with potent activity toward <i>Escherichia coli</i> and <i>Pseudomonas aeruginosa</i>. |
|
dc.format.medium |
Print-Electronic |
|
dc.language |
eng |
|
dc.publisher |
American Chemical Society (ACS) |
|
dc.relation.ispartofseries |
Accounts of chemical research |
|
dc.rights |
Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. |
|
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
|
dc.subject |
Gram-Positive Bacteria |
|
dc.subject |
Ozone |
|
dc.subject |
Alamethicin |
|
dc.subject |
Daptomycin |
|
dc.subject |
Peptides |
|
dc.subject |
Bacteriocins |
|
dc.subject |
Anti-Bacterial Agents |
|
dc.subject |
Microbial Sensitivity Tests |
|
dc.subject |
Drug Evaluation, Preclinical |
|
dc.subject |
Drug Resistance, Multiple, Bacterial |
|
dc.subject |
Amino Acid Sequence |
|
dc.subject |
Structure-Activity Relationship |
|
dc.subject |
Lipopeptides |
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dc.subject |
Rare Diseases |
|
dc.subject |
Tuberculosis |
|
dc.subject |
Emerging Infectious Diseases |
|
dc.subject |
Antimicrobial Resistance |
|
dc.subject |
Vaccine Related |
|
dc.subject |
Infectious Diseases |
|
dc.subject |
2 Aetiology |
|
dc.subject |
5 Development of treatments and therapeutic interventions |
|
dc.subject |
5.1 Pharmaceuticals |
|
dc.subject |
2.2 Factors relating to the physical environment |
|
dc.subject |
Infection |
|
dc.subject |
3 Good Health and Well Being |
|
dc.subject |
Science & Technology |
|
dc.subject |
Physical Sciences |
|
dc.subject |
Chemistry, Multidisciplinary |
|
dc.subject |
Chemistry |
|
dc.subject |
SOLID-PHASE SYNTHESIS |
|
dc.subject |
CYCLIC LIPOPEPTIDE |
|
dc.subject |
CHEMICAL-SYNTHESIS |
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dc.subject |
GLYCOPEPTIDE |
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dc.subject |
AMINOLIPOPEPTIDES |
|
dc.subject |
INFECTIONS |
|
dc.subject |
03 Chemical Sciences |
|
dc.title |
Discovery, Synthesis, and Optimization of Peptide-Based Antibiotics. |
|
dc.type |
Journal Article |
|
dc.identifier.doi |
10.1021/acs.accounts.0c00841 |
|
pubs.issue |
8 |
|
pubs.begin-page |
1878 |
|
pubs.volume |
54 |
|
dc.date.updated |
2023-02-28T07:11:17Z |
|
dc.rights.holder |
Copyright: The authors |
en |
dc.identifier.pmid |
33750106 (pubmed) |
|
pubs.author-url |
https://www.ncbi.nlm.nih.gov/pubmed/33750106 |
|
pubs.end-page |
1890 |
|
pubs.publication-status |
Published |
|
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RetrictedAccess |
en |
pubs.subtype |
Journal Article |
|
pubs.elements-id |
844733 |
|
pubs.org-id |
Science |
|
pubs.org-id |
Chemistry |
|
pubs.org-id |
Science Research |
|
pubs.org-id |
Maurice Wilkins Centre (2010-2014) |
|
dc.identifier.eissn |
1520-4898 |
|
pubs.record-created-at-source-date |
2023-02-28 |
|
pubs.online-publication-date |
2021-03-22 |
|