Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2014 Aug 11;20(33):10204-12.
doi: 10.1002/chem.201402804. Epub 2014 Jul 10.

Natural product synthesis at the interface of chemistry and biology

Jiyong Hong  1
Affiliations

Natural product synthesis at the interface of chemistry and biology

Jiyong Hong. Chemistry. .

Abstract

Nature has evolved to produce unique and diverse natural products that possess high target affinity and specificity. Natural products have been the richest sources for novel modulators of biomolecular function. Since the chemical synthesis of urea by Wöhler, organic chemists have been intrigued by natural products, leading to the evolution of the field of natural product synthesis over the past two centuries. Natural product synthesis has enabled natural products to play an essential role in drug discovery and chemical biology. With the introduction of novel, innovative concepts and strategies for synthetic efficiency, natural product synthesis in the 21st century is well poised to address the challenges and complexities faced by natural product chemistry and will remain essential to progress in biomedical sciences.

Keywords: chemical biology; drug discovery; natural products; organic synthesis; synthetic efficiency.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Examples of natural product or natural product-derived drugs.
Figure 2
Figure 2
Examples of natural products that have contributed to chemical biology.
Figure 3
Figure 3
Structure of vancomycin and amidinated vancomycin
Figure 4
Figure 4
Structure of diazonamide A and its biotinylated derivative.
Figure 5
Figure 5
Structure of duocarmycins, yatakemycin, and CC-1065.
Figure 6
Figure 6
DNA alkylation model of (+)-duocarmycin SA.
Figure 7
Figure 7
Site-selective functionalization of teicoplanin.
Scheme 1
Scheme 1
The Novartis gram-scale synthesis of (+)-discodermolide.
Scheme 2
Scheme 2
The Eisai synthesis of eribulin mesylate (Halaven®).
Scheme 3
Scheme 3
The Baran synthesis of ingenol.
Scheme 4
Scheme 4
Synthesis of (−)-aromadendranediol by MacMillan and co-workers.
Scheme 5
Scheme 5
Examples of C H functionalization in natural product synthesis.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

  • Towards the sustainable discovery and development of new antibiotics.
    Miethke M, Pieroni M, Weber T, Brönstrup M, Hammann P, Halby L, Arimondo PB, Glaser P, Aigle B, Bode HB, Moreira R, Li Y, Luzhetskyy A, Medema MH, Pernodet JL, Stadler M, Tormo JR, Genilloud O, Truman AW, Weissman KJ, Takano E, Sabatini S, Stegmann E, Brötz-Oesterhelt H, Wohlleben W, Seemann M, Empting M, Hirsch AKH, Loretz B, Lehr CM, Titz A, Herrmann J, Jaeger T, Alt S, Hesterkamp T, Winterhalter M, Schiefer A, Pfarr K, Hoerauf A, Graz H, Graz M, Lindvall M, Ramurthy S, Karlén A, van Dongen M, Petkovic H, Keller A, Peyrane F, Donadio S, Fraisse L, Piddock LJV, Gilbert IH, Moser HE, Müller R. Miethke M, et al. Nat Rev Chem. 2021 Oct;5(10):726-749. doi: 10.1038/s41570-021-00313-1. Epub 2021 Aug 19. Nat Rev Chem. 2021. PMID: 37118182 Review.
  • Endless Resistance. Endless Antibiotics?
    Fisher JF, Mobashery S. Fisher JF, et al. Medchemcomm. 2016 Jan 1;7(1):37-49. doi: 10.1039/C5MD00394F. Epub 2015 Nov 3. Medchemcomm. 2016. PMID: 27746889 Free PMC article.
  • Synthesis and Biological Evaluation of Manassantin Analogues for Hypoxia-Inducible Factor 1α Inhibition.
    Kwon DY, Lee HE, Weitzel DH, Park K, Lee SH, Lee CT, Stephenson TN, Park H, Fitzgerald MC, Chi JT, Mook RA Jr, Dewhirst MW, Lee YM, Hong J. Kwon DY, et al. J Med Chem. 2015 Oct 8;58(19):7659-71. doi: 10.1021/acs.jmedchem.5b01220. Epub 2015 Sep 22. J Med Chem. 2015. PMID: 26394152 Free PMC article.
  • Grafting (S)-2-Phenylpropionic Acid on Coordinatively Unsaturated Metal Centers of MIL-101(Al) Metal-Organic Frameworks for Improved Enantioseparation.
    Zhao R, Bai X, Yang W, Fan K, Zhang H. Zhao R, et al. Materials (Basel). 2022 Nov 27;15(23):8456. doi: 10.3390/ma15238456. Materials (Basel). 2022. PMID: 36499951 Free PMC article.
  • Towards the sustainable discovery and development of new antibiotics.
    Miethke M, Pieroni M, Weber T, Brönstrup M, Hammann P, Halby L, Arimondo PB, Glaser P, Aigle B, Bode HB, Moreira R, Li Y, Luzhetskyy A, Medema MH, Pernodet JL, Stadler M, Tormo JR, Genilloud O, Truman AW, Weissman KJ, Takano E, Sabatini S, Stegmann E, Brötz-Oesterhelt H, Wohlleben W, Seemann M, Empting M, Hirsch AKH, Loretz B, Lehr CM, Titz A, Herrmann J, Jaeger T, Alt S, Hesterkamp T, Winterhalter M, Schiefer A, Pfarr K, Hoerauf A, Graz H, Graz M, Lindvall M, Ramurthy S, Karlén A, van Dongen M, Petkovic H, Keller A, Peyrane F, Donadio S, Fraisse L, Piddock LJV, Gilbert IH, Moser HE, Müller R. Miethke M, et al. Nat Rev Chem. 2021;5(10):726-749. doi: 10.1038/s41570-021-00313-1. Epub 2021 Aug 19. Nat Rev Chem. 2021. PMID: 34426795 Free PMC article. Review.
See all "Cited by" articles

References

    1. Wohler F. Ann Phys. 1828;88:253–256.
    1. Hoffmann RW. Angew Chem Int Ed. 2013;52:123–130. - PubMed
    1. Firn RD, Jones CG. Nat Prod Rep. 2003;20:382–391. - PubMed
    1. Bon RS, Waldmann H. Acc Chem Res. 2010;43:1103–1114. - PubMed
    1. Newman DJ, Cragg GM. J Nat Prod. 2012;75:311–335. - PMC - PubMed

Publication types

MeSH terms

LinkOut - more resources