1192188-20-7Relevant academic research and scientific papers
Expedient synthesis of α,α-dimethyl-β-hydroxy carbonyl scaffolds via Evans' aldol reaction with a tertiary enolate
Nunnery, Joshawna K.,Suyama, Takashi L.,Linington, Roger G.,Gerwick, William H.
supporting information; experimental part, p. 2929 - 2932 (2011/06/23)
An efficient synthetic methodology for 3-hydroxy-2,2-dimethyloctynoic acid (DHOYA) and several variants, which are increasingly common fragments encountered in bioactive marine cyanobacterial metabolites, was developed. These fragments were obtained in three steps via a tertiary aldol reaction utilizing an Evans' chiral auxiliary to afford the desired stereochemistry at the β-hydroxy carbon. Thus far, this methodology has been successfully applied in determination of the absolute stereochemistry of eight cyanobacterial natural products, including the VGSC activator palymramide A.
Palmyramide a, a cyclic depsipeptide from a palmyra atoll collection of the marine cyanobacterium lyngbya majuscula
Taniguchi, Masatoshi,Nunnery, Josbawna K.,Engene, Niclas,Esquenazi, Eduardo,Byrum, Tara,Dorrestein, Pieter C.,Gerwick, William H.
experimental part, p. 393 - 398 (2010/07/06)
Bioassay-guided fractionation of the extract of a consortium of a marine cyanobacterium and a red alga (Rhodophyta) led to the discovery of a novel compound, palmyramide A, along with the known compounds curacin D and malyngamide C. The planar structure of palmyramide A. was determined by one- and two-dimensional NMR studies and mass spectrometry. Palmyramide A is a cyclic depsipeptide that features an unusual arrangement of three amino acids and three hydroxy acids; one of the hydroxy acids is the rare 2, 2-dimethyl-3- hydroxyhexanoic acid unit (Dmhha). The absolute configurations of the six residues were determined by Marfey's analysis, chiral HPLC analysis, and GC/MS analysis of the hydrolysate. Morphological and phylogenetic studies revealed the sample to be composed of a Lyngbya majuscula-Centroceras sp. association. MALDI-imaging analysis of the cultured L majuscula indicated that it was the true producer of this new depsipeptide. Pure palmyramide A showed sodium channel blocking activity in neuro-2a cells and cytotoxic activity in. H-460 human lung carcinoma cells.
