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Natural macrocyclic molecules have a possible limited structural diversity

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Abstract

This paper examines ring size patterns of natural product macrocycles. Evidence is presented that natural macrocycles containing 14-, 16-, and 18-membered rings are of frequent occurrence based on a data mining study. The results raise a question about the limited diversity of macrocycle ring sizes and the nature of the constraints that may cause them. The data suggest that the preference bears no relationship to the odd–even frequency in natural fatty acids. The trends reported here, along with those reported previously (Wessjohann et al. (2005) Mol Divers 9:171), may be generalized to better understand the possible structure preferences of natural macrocycles.

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Authors and Affiliations

  1. Departments of Chemistry, The Graduate Center and City, University of New York (CUNY), Brooklyn College, Brooklyn, NY, 11210, USA

    Aaron T. Frank, Nicola S. Farina, Nahed Sawwan, Orrette R. Wauchope, Mo Qi, Edyta M. Brzostowska, Wang Chan, Paul Haberfield & Alexander Greer

  2. Department of Psychology, The Graduate Center and City, University of New York (CUNY), Brooklyn College, Brooklyn, NY, 11210, USA

    Frank W. Grasso

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  1. Aaron T. Frank
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  2. Nicola S. Farina
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  3. Nahed Sawwan
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  4. Orrette R. Wauchope
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  5. Mo Qi
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  6. Edyta M. Brzostowska
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  7. Wang Chan
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  8. Frank W. Grasso
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  9. Paul Haberfield
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  10. Alexander Greer
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Correspondence to Alexander Greer.

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Frank, A.T., Farina, N.S., Sawwan, N. et al. Natural macrocyclic molecules have a possible limited structural diversity. Mol Divers 11, 115–118 (2007). https://doi.org/10.1007/s11030-007-9065-5

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  • DOI: https://doi.org/10.1007/s11030-007-9065-5

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