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Related Experiment Video

Updated: Jul 10, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Natural macrocyclic molecules have a possible limited structural diversity.

Aaron T Frank¹, Nicola S Farina, Nahed Sawwan

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

Molecular Diversity

|November 21, 2007

Summary

Natural product macrocycles frequently feature 14-, 16-, and 18-membered rings. This study questions the limited diversity in macrocycle ring sizes and their underlying constraints, finding no link to fatty acid odd-even frequencies.

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Area of Science:

Natural Product Chemistry
Chemical Biology
Organic Chemistry

Background:

Macrocycles are large cyclic molecules prevalent in natural products.
Understanding the structural diversity and formation preferences of natural macrocycles is crucial for drug discovery and chemical biology.
Previous studies have hinted at non-random distributions in macrocycle ring sizes.

Purpose of the Study:

To investigate ring size patterns in naturally occurring macrocycles.
To identify frequently occurring ring sizes in natural product macrocycles.
To explore potential constraints limiting the diversity of macrocycle ring sizes.

Main Methods:

Data mining of natural product macrocycle structures.
Statistical analysis of ring size distribution.
Comparison with natural fatty acid chain lengths.

Main Results:

Natural product macrocycles with 14-, 16-, and 18-membered rings are frequently observed.
The observed ring size distribution does not correlate with the odd-even frequency of natural fatty acids.
A limited diversity in macrocycle ring sizes was identified.

Conclusions:

The prevalence of specific ring sizes (14, 16, 18) suggests underlying biosynthetic or structural preferences.
The observed patterns are not explained by simple analogies to fatty acid synthesis.
Further investigation into the constraints governing natural macrocycle formation is warranted.