The intertwining of human and technological in a digital native community

Strength by Joining Methods: Combining Synthesis with NMR, IR, and Vibrational Circular Dichroism Spectroscopy for the Determination of the Relative Configuration in Hemicalide

“…However, we see no reason not to use this algorithm on the comparison of two experimental model compounds (samples I and II) with the natural product. [2] The analysis shows that there is a 98.5 % chance that sample I has the same relative configuration as hemicalide, confirming the manual assignment ( Table 2).…”

“…Recently, researchers of the CNRS-Pierre Fabre Laboratories, in collaboration with the Institut de Recherche pour le DØveloppement (IRD), isolated for the first time a complex bioactive polyketide from the marine sponge Hemimycale sp., collected in deep water around the Torres Islands (Vanuatu). [2] This new natural product, called hemicalide, is a highly potent mitotic blocker that, at subnanomolar concentrations and by a unique mechanism, exhibits antiproliferative activity against several human cancer cell lines. [2] Extensive NMR studies enabled the determination of the structure of hemicalide, which features a 46-carbon-atom backbone containing 21 stereocenters (Figure 1).…”

“…[2] This new natural product, called hemicalide, is a highly potent mitotic blocker that, at subnanomolar concentrations and by a unique mechanism, exhibits antiproliferative activity against several human cancer cell lines. [2] Extensive NMR studies enabled the determination of the structure of hemicalide, which features a 46-carbon-atom backbone containing 21 stereocenters (Figure 1). [2] Unfortunately, due to the extremely limited supply of hemicalide (< 1 mg), degradation and derivatization experiments could not be carried out, and hence the configuration of the stereocenters could not be assigned.…”

“…[2] Extensive NMR studies enabled the determination of the structure of hemicalide, which features a 46-carbon-atom backbone containing 21 stereocenters (Figure 1). [2] Unfortunately, due to the extremely limited supply of hemicalide (< 1 mg), degradation and derivatization experiments could not be carried out, and hence the configuration of the stereocenters could not be assigned. However, the promising biological activity of hemicalide stimulated further studies concerning the assignment of the relative configuration of the stereocenters in the key structural subunits, as part of an ambitious program devoted to the total synthesis of this natural product and analogues thereof.…”

Marine natural products

“…This potent (sub-nM) inhibitor of mitosis was sourced from a deep water sponge collected at the Torres Islands, Vanuatu, but to date has only been reported in a patent. 516,517 A series of peroxides 768-773, 518 halogenated alkenes 774 and 775, 519 and an amide 776 520 have been reported from Plakortis simplex, Dysidea sp. and Anoxycalyx (Scolymastra) joubini, respectively.…”