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Large-scale Asymmetric Synthesis of the Bioprotective Agent JP4-039 and Analogs

Overview
Journal Org Lett
Specialties Biochemistry
Chemistry
Date 2011 Apr 2
PMID 21452836
Citations 21
Authors
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Abstract

JP4-039 is a novel nitroxide conjugate capable of crossing lipid bilayer membranes and scavenging reactive oxygen species (ROS). An efficient and scalable one-pot hydrozirconation-transmetalation-imine addition methodology has been developed for its asymmetric preparation. Furthermore, this versatile methodology allows for the synthesis of cyclopropyl and fluorinated analogs of the parent lead structure.

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References
1.
Jiang J, Belikova N, Hoye A, Zhao Q, Epperly M, Greenberger J . A mitochondria-targeted nitroxide/hemigramicidin S conjugate protects mouse embryonic cells against gamma irradiation. Int J Radiat Oncol Biol Phys. 2008; 70(3):816-25. PMC: 2527544. DOI: 10.1016/j.ijrobp.2007.10.047. View

2.
Kagan V, Wipf P, Stoyanovsky D, Greenberger J, Borisenko G, Belikova N . Mitochondrial targeting of electron scavenging antioxidants: Regulation of selective oxidation vs random chain reactions. Adv Drug Deliv Rev. 2009; 61(14):1375-85. PMC: 2784017. DOI: 10.1016/j.addr.2009.06.008. View

3.
Wipf P, Xiao J, Stephenson C . Peptide-Like Molecules (PLMs): A Journey from Peptide Bond Isosteres to Gramicidin S Mimetics and Mitochondrial Targeting Agents. Chimia (Aarau). 2010; 63(11):764-775. PMC: 2922051. DOI: 10.2533/chimia.2009.764. View

4.
Xiao J, Weisblum B, Wipf P . Electrostatic versus steric effects in peptidomimicry: synthesis and secondary structure analysis of gramicidin S analogues with (E)-alkene peptide isosteres. J Am Chem Soc. 2005; 127(16):5742-3. DOI: 10.1021/ja051002s. View

5.
Wipf P, Pierce J . Expedient synthesis of the alpha-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000). Org Lett. 2006; 8(15):3375-8. DOI: 10.1021/ol0613057. View