title: Natural macrocyclic molecules have a possible limited structural diversity.
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.
authors.affiliation: Departments of Chemistry, The Graduate Center and City University of New York, Brooklyn College, Brooklyn, NY 11210, USA.
authors.forename: Aaron T
authors.initials: AT
authors.lastname: Frank
authors.forename: Nicola S
authors.initials: NS
authors.lastname: Farina
authors.forename: Nahed
authors.initials: N
authors.lastname: Sawwan
authors.forename: Orrette R
authors.initials: OR
authors.lastname: Wauchope
authors.forename: Mo
authors.initials: M
authors.lastname: Qi
authors.forename: Edyta M
authors.initials: EM
authors.lastname: Brzostowska
authors.forename: Wang
authors.initials: W
authors.lastname: Chan
authors.forename: Frank W
authors.initials: FW
authors.lastname: Grasso
authors.forename: Paul
authors.initials: P
authors.lastname: Haberfield
authors.forename: Alexander
authors.initials: A
authors.lastname: Greer
mesh_terms: D001688:Biological Products / Q000737:chemistry*; D003500:Cyclization; D005227:Fatty Acids / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009792:Oceans and Seas
chemical_list: D001688:Biological Products; D005227:Fatty Acids; D047028:Macrocyclic Compounds