Key words (±)-saxitoxin - paralytic shellfish toxins Eschenmoser sulfide contraction Biginelli reaction Curtius rearrangement Meerwein's salt

In a simple procedure, the intramolecular hydroarylation of N-propargyl-pyrrole-2-carboxamides was accomplished with the aid of gold(III) catalysis. The reaction led to differently substituted pyrrolo[2,3-c]pyridine and pyrrolo[3,2-c]pyridine derivatives arising either from direct cyclization or from a formal rearrangement of the carboxamide group. Terminal alkynes are essential to achieve bicy...

The integration of electro and bio-catalysis offers new ways making molecules under very mild, environmentally benign conditions. We show that TEMPO mediated electro-catalytic oxidation alcohols can be adapted to work in aqueous buffers, with minimal organic co-solvent, enabling biocatalytic reductive amination using the AdRedAm enzyme. combined process a approach amine alkylation native alcoho...

Although several methods for the preparation of 4o propargyl indole derivatives have been published, this synthetic transformation is complicated by the tendency of 3o propargyl alcohols to form allenium intermediates in acidic media.  It is therefore a challenge to find an efficient method for the C-3 propargylation of indoles with 3° propargylic alcohols.  In this pa...

Introduction The discovery that complex chiral diacetylene derivatives can self-assemble into nanostructures 1 has led to a search for simpler molecules that retain that activity. The search for novel materials is complicated because the factors governing self-assembly are complex and until the simple system is identified the underlying mechanisms are difficult to discover. Unlike spherical lip...

The formation of gold nanoparticle–lipid composite films by glucose-induced reduction of chloroaurate ions entrapped in thermally evaporated fatty amine films is described. Simple immersion of films of the salt of octadecylamine and chloroaurate ions (formed by immersion of thermally evaporated fatty amine films in chloroauric acid solution) in glucose solution leads to the facile in-situ reduc...

We show that salt bridges involving lysines can be detected by deuterium isotope effects on NMR chemical shifts of the sidechain amine. Lys27 in the ribonuclease barnase is salt bridged, and mutation of Arg69 to Lys retains a partially buried salt bridge. The salt bridges are functionally important.

although several methods for the preparation of 4o propargyl indole derivatives have been published, this synthetic transformation is complicated by the tendency of 3o propargyl alcohols to form allenium intermediates in acidic media.  it is therefore a challenge to find an efficient method for the c-3 propargylation of indoles with 3° propargylic alcohols.  in this paper we wish to report on t...

Despite the prevalence of head-to-side chain threonine linkages in natural products, their incorporation has been underexplored in synthetic cyclic peptides. Herein we investigate a cyclic peptide scaffold able to undergo an N-O acyl rearrangement. Upon acylation of the amine with diverse carboxylic acids, the resulting cyclic depsipeptides displayed favorable cellular permeability and a confor...