Potent Antibiotic Lemonomycin: A Glimpse of Its Discovery, Origin, and Chemical Synthesis

Abstract

Lemonomycin (1) was first isolated from the fermentation broth of Streptomyces candidus in 1964. The complete chemical structure was not elucidated until 2000 with extensive spectroscopic analysis. Lemonomycin is currently known as the only glycosylated tetrahydroisoquinoline antibiotic. Its potent antibacterial activity against Staphylococcus aureus and Bacillus subtilis and complex architecture make it an ideal target for total synthesis. In this short review, we summarize the research status of lemonomycin for biological activity, biosynthesis, and chemical synthesis. The unique deoxy aminosugar-lemonose was proposed to play a crucial role in biological activity, as shown in other antibiotics, such as arimetamycin A, nocathiacin I, glycothiohexide α, and thiazamycins. Given the self-resistance of the original bacterial host, the integration of biosynthesis and chemical synthesis to pursue efficient synthesis and further derivatization is in high demand for the development of novel antibiotics to combat antibiotic-resistant infections.

Enhanced catalytic performance of penicillin G acylase by covalent immobilization onto functionally-modified magnetic Ni0.4Cu0.5Zn0.1Fe2O4 nanoparticles

“…Nevertheless, until such alternatives are identified, antibiotics will maintain their pivotal role. Antibiotics are presently synthesized through various methods, including fermentation [9], chemical synthesis [10,11], and enzymatic (semi-synthetic) methods [12]. The fermentation method is susceptible to the influence of various factors, impacting the quality of the process, making product separation challenging, and often resulting in lower purity.…”

All-in-One Synthesis of 3,6-Dideoxysugars: An Olefin Metathesis–Isomerization Approach

“…During our recent efforts toward the synthesis of amino deoxysugars in prominent antibiotics via the nitroso–ene reaction, an initial attempt was made using the Grubbs-II (G-II) catalyst that resulted in olefin migration to afford ethyl ketone 3 and vinyl ether 4a (Scheme a). Olefin migration is a common and well-known phenomenon in metathesis and is considered to be a repellent and undesirable side process .…”