Beilstein J. Org. Chem.2024,20, 589–596, doi:10.3762/bjoc.20.51
Michael O. Akintubosun Melanie A. Higgins Department of Biological Sciences, The University of Alabama, 3314 Science and Engineering Complex, Tuscaloosa, AL 35487, USA 10.3762/bjoc.20.51 Abstract HygromycinA is a broad-spectrum antibiotic that contains a furanose, cinnamic acid, and
family containing Hyg17 and discuss genome mining strategies that target this protein family to identify biosynthetic clusters for natural product discovery.
Keywords: aminocyclitol; biosynthesis; hygromycinA; inositol dehydrogenase; myo-inositol; Introduction
HygromycinA is a natural product that
peptidyl transferase activity while the furanose group does not appear to be important for target inhibition [6][7]. In addition, hygromycinA contains a unique methylenedioxy group found on the aminocyclitol that is not required for ribosome interaction and in vitro inhibition [8]. Instead, it is
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Graphical Abstract
Figure 1:
Proposed biosynthetic pathway for the aminocyclitol from hygromycin A.
Beilstein J. Org. Chem.2018,14, 1619–1636, doi:10.3762/bjoc.14.138
of hygromycinA, Donohoe et al. used a Mitsunobu glycosylation of 84 with the arabinose derivative 83. This reaction could be tuned to deliver the required β-arabinofuranoside building block 85 with high stereoselectivity and under the assistance of triisopropylsilyl (TIPS) protecting groups (Scheme
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Graphical Abstract
Scheme 1:
Left: The Mitsunobu reaction is essentially a nucleophilic substitution of alcohols occurring with ...