Recent advances in the field of bioactive tetronates

Abstract

Covering: up to mid-2014 Over the last several decades, the number of pharmacologically active natural products has significantly increased and several natural product families have taken shape. This review highlights the family of tetronate and spirotetronate compounds, which show a vast structural and functional diversity. The rapid growth of this group has created the need for a comprehensive overview and classification system, which we have devised based on structural characteristics. An updated overview is provided based on known tetronates, intended to spur further research in this field by identifying common structural features and general principles of their biosynthesis. We also compare a selection of chemical syntheses of representative compounds belonging to individual subtypes, both in terms of their efficiency as well as the extent to which they are biomimetic. This review also summarizes progress in unraveling some of the principles underlying the potent and varied bioactivities of natural tetronate antibiotics, and in identifying and better understanding their structure–activity relationships and modes of action.DFG, EXC 314, Unifying Concepts in Catalysi

29-Deoxymaklamicin, a new maklamicin analogue produced by a genetically engineered strain of Micromonospora sp. NBRC 110955

“…The biosynthetic mechanism of the spirotetronate-class antibiotics has been shown to include a polyketide assembly line, a glycerate utilization system, a sugar modification, and a novel [4 þ 2]-cycloaddition system for the spirotetronate skeleton (5,16).…”

Tetrodecamycin: An unusual and interesting tetronate antibiotic

“…This family was recently divided into three subfamilies: the linear tetronates, the spirotetronates, and the miscellaneous tetronates. 15 The linear tetronates are epitomized by molecules such as agglomerin A, 16 acaterin, 17 didehydro-acaterin, 18 RK-682, 12 pesthetoxin, 19 and tetronomycin 20 (Fig. 1B).…”

Characterization of the biosynthetic gene cluster for maklamicin, a spirotetronate-class antibiotic of the endophytic Micromonospora sp. NBRC 110955

“…The spirotetronate-class antibiotics are a growing family of polyketide natural products with a wide range of biological activities, including anti-bacterial, anti-tumor, and anti-viral activities (Vieweg et al 2014). The compounds in this family possess a characteristic tetronate moiety spiro-linked to a cyclohexene ring, sometimes conjugated with a trans-decalin moiety.…”