75452-47-0Relevant articles and documents
Stereoselective synthesis of 17,18-epoxy derivative of EPA and stereoisomers of isoleukotoxin diol by ring opening of TMS-substituted epoxide with dimsyl sodium
Nanba, Yutaro,Shinohara, Riku,Morita, Masao,Kobayashi, Yuichi
, p. 8614 - 8626 (2017/10/27)
The reaction of TMS-substituted epoxy alcohols (and derivatives) with dimsyl sodium (NaDMSO) to give 1-alkene-3,4-diols was used for the synthesis of enantiomerically enriched 17(R),18(S)-EpETE and two diastereoisomers of isoleukotoxin diol. In the synthesis of 17(R),18(S)-EpETE, the α-ethoxyethyl ether (EE) of the epoxy alcohol derived from (R)-1-TMS-1-penten-3-ol underwent reaction with NaDMSO to give the mono EE-protected 1-hexene-3,4-diol. The aldehyde obtained by hydroboration/oxidation was subjected to Wittig reaction to afford a mono EE-protected diol. The corresponding mono mesylate was prepared and subjected to epoxide ring formation to afford 17(R),18(S)-EpETE stereoselectively. Similarly, a reaction of the anti epoxy alcohol derived from (R)-1-TMS-1-octen-3-ol with NaDMSO gave the anti form of 1-nonene-3,4-diol, which was converted to 12(S),13(R)-isoleukotoxin diol through Wittig reaction. 12(R),13(R)-Isoleukotoxin diol was synthesized in a similar manner.
Design, synthesis, and operation of small molecules that walk along tracks
Von Delius, Max,Geertsema, Edzard M.,Leigh, David A.,Tang, Dan-Tam D.
, p. 16134 - 16145 (2011/02/16)
The synthesis and system dynamics of a series of small-molecule walker-track conjugates, 3,4-Cn (n = 2, 3, 4, 5, and 8), based on dynamic covalent linkages between the "feet" of the walkers and the "footholds" of the track, is described. Each walker has one acyl hydrazide and one sulfur-based foot separated by a spacer chain of "n" methylene groups, while the track consists of four footholds of alternating complementary functionalities (aldehydes and masked thiols). Upon repeatedly switching between acid and base, the walker moiety can be exchanged between the footholds on the track, primarily through a "passing-leg gait" mechanism, until a steady state, minimum energy, distribution is reached. The introduction of a kinetically controlled step in the reaction sequence (redox-mediated breaking and reforming of the disulfide linkages) can cause a directional bias in the distribution of the walker on the track. The different length walker molecules exhibit very different walking behaviors: Systems n = 2 and 3 cannot actually "walk" along the track because their stride lengths are too short to bridge the internal footholds. The walkers with longer spacers (n = 4, 5, and 8) do step up and down the track repeatedly, but a directional bias under the acid-redox conditions is only achieved for the C 4 and C5 systems, interestingly in opposite directions (the C8 walker has insufficient ring strain with the track). Although they are extremely rudimentary systems, the C4 and C5 walker-track conjugates exhibit four of the essential characteristics of linear molecular motor dynamics: processive, directional, repetitive, and progressive migration of a molecular unit up and down a molecular track.
Synthesis and activity of nonhydrolyzable pseudomonic acid analogues
Klein,Yeung,Kurath,Mao,Fernandes,Lartey,Pernet
, p. 151 - 160 (2007/10/02)
Several series of pseudomonic acid analogues have been prepared that incorporate modified functionalities in place of the C1-C3 α,β-unsaturated ester group. The inhibition of isoleucyl-tRNA synthetase and the in vitro activity of these compounds against various Gram-positive and Gram-negative strains are described. Several derivatives showed enzyme inhibition equivalent to or better than that of methyl pseudomonate (3), while lacking the hydrolyzable ester group at C1. These analogues include the corresponding phenyl ketone and the ether 12. The long-chain ketone 24 exhibited similar in vitro activity as the parent ester.
