- Versatile Synthetic Route to Cycloheximide and Analogues That Potently Inhibit Translation Elongation
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Cycloheximide (CHX) is an inhibitor of eukaryotic translation elongation that has played an essential role in the study of protein synthesis. Despite its ubiquity, few studies have been directed towards accessing synthetic CHX derivatives, even though such efforts may lead to protein synthesis inhibitors with improved or alternate properties. Described here is the total synthesis of CHX and analogues, and the establishment of structure–activity relationships (SAR) responsible for translation inhibition. The SAR studies aided the design of more potent compounds, one of which irreversibly blocks ribosomal elongation, preserves polysome profiles, and may be a broadly useful tool for investigating protein synthesis.
- Park, Yongho,Koga, Yumi,Su, Cindy,Waterbury, Amanda L.,Johnny, Christopher L.,Liau, Brian B.
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p. 5387 - 5391
(2019/03/26)
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- Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules
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Nitrogen heterocycles are ubiquitous in natural products and pharmaceuticals. Herein, we disclose a nitrogen complexation strategy that employs a strong Bronsted acid (HBF4) or an azaphilic Lewis acid (BF3) to enable remote, non-directed C(sp3)-H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization.
- Howell, Jennifer M.,Feng, Kaibo,Clark, Joseph R.,Trzepkowski, Louis J.,White, M. Christina
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supporting information
p. 14590 - 14593
(2015/12/08)
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- Syntheses and biological activities of (+/-)-streptovitacin A and E-73.
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(+/-)-Streptovitacin A (1) and its stereoisomers were synthesized by an aldol reaction of (+/-)-2,4-dimethyl-4-trimethylsiloxy-1-cyclohexanones (4b and 9) with 4-(2-oxoethyl)-2,6-piperidinedione (5). E-72 (2) was derived from synthetic 1. (+/-)-1 showed m
- Kondo,Oritani,Yamashita
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p. 1531 - 1536
(2007/10/02)
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