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dc.contributor.authorHutt, Oliver E.
dc.contributor.authorInagaki, Jun
dc.contributor.authorReddy, Bollu S.
dc.contributor.authorNair, Sajiv K.
dc.contributor.authorReiff, Emily A.
dc.contributor.authorHenri, John T.
dc.contributor.authorGreiner, Jack F.
dc.contributor.authorVanderVelde, David G.
dc.contributor.authorChiu, Ting-Lan
dc.contributor.authorAmin, Elizabeth A.
dc.contributor.authorHimes, Richard H.
dc.contributor.authorGeorg, Gunda I.
dc.date.accessioned2017-05-04T19:10:31Z
dc.date.available2017-05-04T19:10:31Z
dc.date.issued2009-06-15
dc.identifier.citationHutt, O. E., Inagaki, J., Reddy, B. S., Nair, S. K., Reiff, E. A., Henri, J. T., … Georg, G. I. (2009). Total synthesis and evaluation of 22-(3-azidobenzoyloxy)methyl epothilone C for photoaffinity labeling of β-tubulin. Bioorganic & Medicinal Chemistry Letters, 19(12), 3293–3296. http://doi.org/10.1016/j.bmcl.2009.04.077en_US
dc.identifier.urihttp://hdl.handle.net/1808/23895
dc.description.abstractThe total synthesis of 22-(3-azidobenzoyloxy)methyl epothilone C is described as a potential photoaffinity probe to elucidate the β-tubulin binding site. A sequential Suzuki-aldol-Yamaguchi macrolactonization strategy was utilized employing a novel derivatized C1–C6 fragment. The C22-functionalized analog exhibited good activity in microtubule assembly assays, but cytotoxicity was significantly reduced. Molecular modeling simulations indicated that excessive steric bulk in the C22 position is accommodated by the large hydrophobic pocket of the binding site. Photoaffinity labeling studies were inconclusive suggesting non-specific labeling.en_US
dc.publisherElsevieren_US
dc.rightsThis article is made available under an Attribution-NonCommercial-NoDerivs 3.0 United States (CC BY-NC-ND 3.0 US) License.en_US
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/3.0/us/en_US
dc.subjectEpothiloneen_US
dc.subjectPhotoaffinity labelsen_US
dc.subjectMicrotubulesen_US
dc.titleTotal synthesis and evaluation of 22-(3-azidobenzoyloxy)methyl epothilone C for photoaffinity labeling of β-tubulinen_US
dc.typeArticleen_US
kusw.kuauthorHutt, Oliver E.
kusw.kuauthorInagaki, Jun
kusw.kuauthorReddy, Bollu S.
kusw.kuauthorNair, Sajiv K.
kusw.kuauthorReiff, Emily A.
kusw.kuauthorGreiner, Jack F.
kusw.kuauthorVanderVelde, David G.
kusw.kuauthorGeorg, Gunda I.
kusw.kuauthorHimes, Richard H.
kusw.kudepartmentMedicinal Chemistryen_US
kusw.kudepartmentMolecular Bioscienceen_US
kusw.oanotesPer SherpaRomeo on 05/04/2017: Author's Pre-print: green tick author can archive pre-print (ie pre-refereeing) Author's Post-print: green tick author can archive post-print (ie final draft post-refereeing) Publisher's Version/PDF: cross author cannot archive publisher's version/PDF General Conditions: Authors pre-print on any website, including arXiv and RePEC Author's post-print on author's personal website immediately Author's post-print on open access repository after an embargo period of between 12 months and 48 months Permitted deposit due to Funding Body, Institutional and Governmental policy or mandate, may be required to comply with embargo periods of 12 months to 48 months Author's post-print may be used to update arXiv and RepEC Publisher's version/PDF cannot be used Must link to publisher version with DOI Author's post-print must be released with a Creative Commons Attribution Non-Commercial No Derivatives Licenseen_US
dc.identifier.doi10.1016/j.bmcl.2009.04.077en_US
kusw.oaversionScholarly/refereed, author accepted manuscripten_US
kusw.oapolicyThis item meets KU Open Access policy criteria.en_US
dc.identifier.pmidPMC2803616en_US
dc.rights.accessrightsopenAccess


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This article is made available under an Attribution-NonCommercial-NoDerivs 3.0 United States (CC BY-NC-ND 3.0 US) License.
Except where otherwise noted, this item's license is described as: This article is made available under an Attribution-NonCommercial-NoDerivs 3.0 United States (CC BY-NC-ND 3.0 US) License.