The Complete Structure of Maitotoxin, Part I: Configuration of the C1C14 Side Chain

Molecular Knots

“…The 268 C. Dietrich-Buchecker et al One-pot preparation of the first metallo-catenane (=catenate) 11 + [43] latter reacts with two equivalents of di-iodo derivative of pentaethylene glycol under high-dilution conditions in the presence of cesium carbonate in dimethylformamide. By this very convenient one-pot synthesis, the expected copper(I) [2]catenate 11 + could be obtained in 27% yield. It should be noted that, more recently, two different, also highly efficient template catenane syntheses have been developed; one of them, first introduced by Stoddart and his coworkers [45] is based on the p-donor/p-acceptor gathering effect between aromatic nuclei, whereas in the second one, mainly developed by Hunter and Vögtle and their coworkers, gathering and orientation of the various subunits of the future catenane are induced by hydrogen bondings [46][47][48].…”

“…The same authors also attempted the directed synthesis of a trefoil knot, which relied on the use of a benzo-acetal central core [32,33]. These syntheses are closely related to the ones that this group had already used successfully to prepare various [2]-and [3]catenanes [34][35][36][37][38].…”

“…Due to its sophisticated topology, this synthesis must be based on a reliable template intermediate. The work of Vögtle and coworkers on the templated synthesis of [2]catenanes based on hydrogen bonds serendipitously led to a very efficient preparation of a molecular knot [88]. In the course of the synthesis of [n]catenanes, the macrocycle 21, presenting two concave 278 C. Dietrich-Buchecker et al 18 Templated synthesis of molecular trefoil knot 25 based on hydrogen bond-sets sites for hydrogen bonding interactions, was identified as a good intermediate.…”

“…b Escher: the trefoil knot [4] Fig. 2 First fifteen prime knots and interlaces closely related to modern molecular sciences. The simplicity of his view of the trefoil knot makes it particularly attractive (Fig.…”

Bioorganic Studies Utilizing Rationally Designed Synthetic Molecules: Absolute Configuration of Ciguatoxin and Development of Immunoassay Systems

“…More importantly, mAb 10C9 bound tightly to CTX3C itself with a comparable K d value of 2.8 nM, and it showed no cross-reactivity with the other IJKLM-ring 45 or with structurally related marine toxins (Fig. 11) including brevetoxin A (BTX A), 22 brevetoxin B (BTX B), 44 okadaic acid (OA), 45 and maitotoxin (MTX). 46 Furthermore, we determined that the K d values of 10C9 for the ABCD-ring 40 and the ABC-ring 32 were 1.8 and 74 mM, respectively, and that for the ABCDE-ring 41 was 0.8 nM (Table 2).…”