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A twist of nature-the significance of atropisomers in biological systems

Journal Article


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Abstract


  • Recently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A–F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized.

Authors


  •   Smyth, Jamie (external author)
  •   Butler, Nicholas (external author)
  •   Keller, Paul A.

Publication Date


  • 2015

Citation


  • Smyth, J. E., Butler, N. M. & Keller, P. A. (2015). A twist of nature-the significance of atropisomers in biological systems. Natural Product Reports: a journal of current development in bioorganic chemistry, 32 (11), 1562-1583.

Scopus Eid


  • 2-s2.0-84945253100

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=4391&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3368

Number Of Pages


  • 21

Start Page


  • 1562

End Page


  • 1583

Volume


  • 32

Issue


  • 11

Abstract


  • Recently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A–F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized.

Authors


  •   Smyth, Jamie (external author)
  •   Butler, Nicholas (external author)
  •   Keller, Paul A.

Publication Date


  • 2015

Citation


  • Smyth, J. E., Butler, N. M. & Keller, P. A. (2015). A twist of nature-the significance of atropisomers in biological systems. Natural Product Reports: a journal of current development in bioorganic chemistry, 32 (11), 1562-1583.

Scopus Eid


  • 2-s2.0-84945253100

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=4391&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3368

Number Of Pages


  • 21

Start Page


  • 1562

End Page


  • 1583

Volume


  • 32

Issue


  • 11