Peter John Murray

The solid phase synthesis of a series of tri-substituted hydantoin ligands for the somatostatin SST5 receptor

A series of trisubstituted hydantoins has been prepared by a versatile solid phase route employing primary alcohols, amines and amino acids as the monomeric building blocks. Several compounds showed submicromolar affinity in binding assays at recombinant human somatostatin receptors.

A novel, chemically robust, amine releasing linker

Abstract A polymer supported sulfonamide 1, based on an amine protective group, has been developed as a novel linker for solid phase organic synthesis. The linker permits the immobilisation of alcohol substrates, and releases N-protected amines under mild nucleophilic cleavage conditions.

Rapid reaction scanning of solid phase chemistry using resins incocorporating analytical constructs

Abstract Two analytical constructs, based on orthogonally cleavable linkers, are reported which facilitate the mass spectral analysis of solid phase chemistry. The chemical compatibility and orthogonality of the linkers were established in a parallel reaction study using contructs prepared specifically for the purpose.

The enantiospecific synthesis of novel lysine analogues incorporating a pyrrolidine containing side chain

Two novel analogues of lysine have been prepared in high enantiomeric and diastereomeric purity. These unnatural α-amino acids possess modified aminoalkyl side chains incorporating a pyrrolidine nucleus as a cyclic constraint.

Versatile solid-phase synthesis of secondary amines from alcohols. Development of an N-Boc-(o-nitrobenzene)sulfonamide linker

The development of a versatile amine releasing linker based on the modified o-nitrobenzene sulfonamide protective group is described. This new N-Boc-o-nitrobenzenesulfonamide (Boc-ONBS) linker enables the elaboration on resin of primary and secondary amines by sequential substitution of the sulfonamide moiety using the Mitsunobu reaction. A 16-member array of secondary and Boc protected primary amines was then prepared using this linker.

A latent aryl hydrazine ‘safety-catch’ linker compatible with N-alkylation

Abstract The preparation and use of a latent aryl hydrazine ‘safety-catch’ linker for solid-phase chemistry, which is compatible with N -alkylation, is reported. Its use is exemplified by the preparation of mono-ketopiperazines, whereby release from resin is effected via an intramolecular cyclitive cleavage strategy.