Total synthesis of (+)-tautomycin

Ichikawa, Yoshiyasu; Tsuboi, Kazuma; Jiang, Yimin; Naganawa, Atsushi; Isobe, Mitsuaki

doi:10.1016/0040-4039(95)01436-l

Cited by 44 publications

(14 citation statements)

References 27 publications

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“…We used a library of 958 small–molecular weight compounds that consists of 209 known inhibitors (including anticancer drugs), three natural compounds, and 746 chemically synthesized compounds. The chemically synthesized compounds were designed to consist of unbiased compounds ( Kusumoto and Oikawa, 2001 ; Oikawa et al. , 1995 , 2005 ; Oikawa, 2010 ).…”

Section: Resultsmentioning

confidence: 99%

Damnacanthal, an effective inhibitor of LIM-kinase, inhibits cell migration and invasion

Ohashi

Sampei

Nakagawa

et al. 2014

MBoC

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Section: Resultsmentioning

confidence: 99%

Damnacanthal, an effective inhibitor of LIM-kinase, inhibits cell migration and invasion

Ohashi

Sampei

Nakagawa

et al. 2014

MBoC

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“…The retrosynthetic analysis of the attenol A shows that the spiroketal moiety 311 can be obtained from ketone diol 312 , which in turn can be accessed from silicon tethered ring-closing metathesis of fragments 314 and 316 . Fragment 314 is prepared from ( tert -butyl-diphenylsiloloxy)-acetaldehyde 315 [ 138 ]. On the other hand the fragment 316 is prepared from known diepoxide 319 via C 2-symmetric diol 318 ( Scheme 70 ) [ 139 ].…”

Section: Asymmetric Total Synthesis Of Natural Spiroketalsmentioning

confidence: 99%

Asymmetric Synthesis of Naturally Occuring Spiroketals

Raju

Saikia

2008

Molecules

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“…TM was purified from a culture of S. spiro erticillatus by the method described previously [14,21]. TM1 and 22-O-methyl TM1 were synthesized by a slight modification of the method that we developed for total synthesis of TM [22,23]. TM2 was synthesized by a method described elsewhere [24].…”

Section: Experimental Materialsmentioning

confidence: 99%

Effects of modification of the hydrophobic C-1‒C-16 segment of tautomycin on its affinity to type-1 and type-2A protein phosphatases

Takai¹,

TSUBOI²,

KOYASU³

et al. 2000

Biochem. J.

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Among the naturally occurring toxins that are known to have specific inhibitory effects on type-1 and type-2A protein phosphatases (PP1 and PP2A), tautomycin (TM) is unique in that it exhibits significantly higher affinity to PP1 than to PP2A. The ratio of the dissociation constant for the PP1-TM interaction to that for the PP2A-TM interaction (the PP1/PP2A ratio) is 0.01-0.03. The aim of the present study was to evaluate the possible contributions of the C-1-C-16 segment of TM to the affinity characteristics of the toxin. The relatively hydrophobic segment contains a spiroketal motif whose enantiomeric form is present in okadaic acid (OA), which exhibits exceedingly higher affinity to PP2A than to PP1. We therefore synthesized two TM analogues: TM1 in which the side chains of the spiroketal motif of TM were removed but its absolute configuration was retained, and TM2 in which the spiroketal motif of TM1 was replaced with its enantiomeric form. The effects of TM, TM1 and TM2 on the activities of the native catalytic subunits of PP1 (PP1C) and PP2A and a recombinant gamma isoform of PP1 (PP1gamma) were examined. The PP1/PP2A ratio determined thereby was 0.2-0.5 for TM1 and 5-10 for TM2. Both the presence of the side chains and the stereochemistry of the spiroketal moieties may be major determining factors for the affinity characteristics of TM. We also show that a monoclonal antibody raised against OA binds to TM2 albeit with much lower affinity than to OA, whereas it exhibits no measurable affinities to TM and TM1.

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Total synthesis of (+)-tautomycin

Cited by 44 publications

References 27 publications

Damnacanthal, an effective inhibitor of LIM-kinase, inhibits cell migration and invasion

Damnacanthal, an effective inhibitor of LIM-kinase, inhibits cell migration and invasion

Asymmetric Synthesis of Naturally Occuring Spiroketals

Effects of modification of the hydrophobic C-1‒C-16 segment of tautomycin on its affinity to type-1 and type-2A protein phosphatases

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