Opines: origins, roles, structures with a nomenclature proposal, and syntheses.

Abstract

Covering: 1927 to 2026.Although discovered almost a century ago, opines represent an ever-growing family of natural products, derived from a variety of organisms, including bacteria, fungi, plants, and marine invertebrates. Opines exhibit a wide variety of structures and play numerous biological roles, some of which have had significant implications in molecular biology, notably in the development of genetically modified organisms (GMOs) and in plant evolution with the recent discovery of natural GMOs. The opines structurally related to N-alkylated α-amino acids are useful chiral building blocks for the pharmaceutical and fine chemical industries, and some of the enzymes involved in their biosynthesis are now being exploited in these industries for drug development. This review first traces the history of opines from 1927 up to now in term of both chemical and biological views; then a new classification with clearer names is proposed mostly based on structural grounds. The various syntheses of opines are described and discussed according to this proposed classification, together with their known applications in biology, chemical biology and chemistry. Finally, several possible directions are highlighted as a roadmap for future research.