First Total Synthesis of Vialinin A, a Novel and Extremely Potent Inhibitor of TNF-α Production

Ye, Yue Qi; Koshino, Hiroyuki; Onose, Jun‐ichi; Yoshikawa, Kunie; Abe, Naoki; Takahashi, Shigetoshi

doi:10.1021/ol701590b

Cited by 36 publications

(21 citation statements)

References 22 publications

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“…Starting from sesamol 6 , we optimized the synthetic route to the methoxymethyl (MOM)‐protected catechol 9 used before for acyl‐DBD dyes, and managed to introduce the desired ethyl esters ( 10 a ) 13. After cleavage, catechol 11 a was cyclized with benzyl‐protected propiolic acid by using 4‐dimethylaminopyridine (DMAP) 9.…”

Section: Resultsmentioning

confidence: 99%

“…The 17-and 32-labelled Gly 13 Cys variant displays fluorescence lifetime changes ( Figure 12) that suggest that the envi-ronment changes from apolar to polar as the lobes of MBP close, because the fluorescence lifetime of 32 decreases by 1.3 ns and that of 17 increases by about 3 ns after the addition of maltose. The reciprocal behavior of the two male-A C H T U N G T R E N N U N G imide labels provides internal confirmation of the consistency of these data, which is consistent with the shift of the emission maxima to longer wavelengths by 4 nm with 32 in the closed conformation, whereas those of 17 remain constant.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

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DBD Dyes as Fluorescence Lifetime Probes to Study Conformational Changes in Proteins

Wawrzinek

Ziomkowska

Heuveling

et al. 2013

Chemistry A European J

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Previously, [1,3]dioxolo[4,5‐f][1,3]benzodioxole (DBD)‐based fluorophores used as highly sensitive fluorescence lifetime probes reporting on their microenvironmental polarity have been described. Now, a new generation of DBD dyes has been developed. Although they are still sensitive to polarity, in contrast to the former DBD dyes, they have extraordinary spectroscopic properties even in aqueous surroundings. They are characterized by long fluorescence lifetimes (10–20 ns), large Stokes shifts (≈100 nm), high photostabilities, and high quantum yields (>0.56). Here, the spectroscopic properties and synthesis of functionalized derivatives for labeling biological targets are described. Furthermore, thio‐reactive maleimido derivatives of both DBD generations show strong intramolecular fluorescence quenching. This mechanism has been investigated and is found to undergo a photoelectron transfer (PET) process. After reaction with a thiol group, this fluorescence quenching is prevented, indicating successful bonding. Being sensitive to their environmental polarity, these compounds have been used as powerful fluorescence lifetime probes for the investigation of conformational changes in the maltose ATP‐binding cassette transporter through fluorescence lifetime spectroscopy. The differing tendencies of the fluorescence lifetime change for both DBD dye generations promote their combination as a powerful toolkit for studying microenvironments in proteins.

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Section: Resultsmentioning

confidence: 99%

Section: Wwwchemeurjorgmentioning

confidence: 99%

DBD Dyes as Fluorescence Lifetime Probes to Study Conformational Changes in Proteins

Wawrzinek

Ziomkowska

Heuveling

et al. 2013

Chemistry A European J

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“…Recently, Takahashi et al have reported the total synthesis of a similar compound vialinin A, by a similar cross-coupling strategy. 4 O O…”

Section: Introductionmentioning

confidence: 99%

Synthesis of ustalic acid, an inhibitor of Na+,K+-ATPase

2008

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“…Preparation of quinone coupling partner 20c was based primarily on the Suzuki coupling strategy charted recently in syntheses of the terphenyl natural products terprenin48 and vialinin A49 (Scheme 6). The tetrabenzyl ether 64 was brominated,50 then coupled48 with boronic acid 66 to form the biaryl 67 .…”

Section: Results and Discusssionmentioning

confidence: 99%

Synthesis-Guided Structure Revision of the Sarcodonin, Sarcoviolin, and Hydnellin Natural Product Family

et al. 2011

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A sweeping structural revision of the sarcodonin natural product family (published structures: 1a–13a) is proposed after extensive studies aimed at their chemical synthesis. Key features of revised structure 1b include replacement of the N,N-dioxide moiety with an oxime, ring opening of the central diketopiperazine, and transposition of the terphenyl wing from the 1β-2β position of 1a to the 2β-3β position of 1b. This structure revision arose from the serendipitous synthesis of a benzodioxane aminal (44) whose structure was unambiguously determined by X-Ray crystallography and whose spectral properties bore considerable resemblance to the published data for the sarcodonins. A versatile new method for O-arylation of hydroxamic acids is also reported herein, as well as a manganese(III)-mediated α-oxidation of hydroxamic acids to aminals.

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First Total Synthesis of Vialinin A, a Novel and Extremely Potent Inhibitor of TNF-α Production

Cited by 36 publications

References 22 publications

DBD Dyes as Fluorescence Lifetime Probes to Study Conformational Changes in Proteins

DBD Dyes as Fluorescence Lifetime Probes to Study Conformational Changes in Proteins

Synthesis of ustalic acid, an inhibitor of Na+,K+-ATPase

Synthesis-Guided Structure Revision of the Sarcodonin, Sarcoviolin, and Hydnellin Natural Product Family

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