Brendan A. Burkett

N-Fmoc-dehydroalanine: a versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids

Abstract The synthesis of polymer-supported N-Fmoc-dehydroalanine starting from S-protected cysteine via an oxidation/elimination strategy is described. Cycloaddition with a range of dienes afforded a range of conformationally constrained amino acids in moderate yields. The potential applications of this methodology to combinatorial libraries is discussed.

The Diels-Alder Reactions of Polymer Bound Dehydroalanine Derivatives

Abstract The synthesis and Diels-Alder cycloadditions of a number of polymer bound dehydroalanine derivatives are described. The studies compare methodologies for accessing polymer bound dehydroalanines and establish the versatility and efficiency of solid phase Diels-Alder reactions in the synthesis of carbocyclic amino acids. These studies nicely complement the growing repertoire of methodologies for the functionalisation of amino acid derivatives.

Guidelines for stereocontrolled Diels–Alder reactions of chiral methylidene piperazine-2,5-diones with cyclopentadiene

Abstract The reactivities and stereoselectivities of Diels–Alder cycloaddition reactions of methylidene piperazine-2,5-diones with cyclopentadiene can be manipulated by appropriate choice of N- and α-carbon substituents. Good to excellent exo/endo and facial selectivities were obtained.

Synthesis of phosphine oxide based amphiphilic molecules via ring-opening Wittig olefination of a macrocyclic phosphoranylidene and their property study as non-ionic surfactants

A novel ring-opening Wittig olefination approach was developed for the synthesis of amphiphilic phosphine oxides (PO) as non-ionic surfactants. The approach concurrently introduces the crucial functional groups (lipophilic chain and phosphine oxide moiety) present in the known PO surfactants and additional hydrophilic group (i.e., ethylene glycol units) in one step via Wittig olefination of a macrocyclic phosphoranylidene. A series of novel PO compounds were obtained from a variety of aldehydes and selected compounds were examined for their physiochemical properties (surface tension, critical micelle concentration and interfacial tension) and also for their abilities to form emulsions as non-ionic surfactants.

Specific Targeting of Melanotic Cells with Peptide Ligated Photosensitizers for Photodynamic Therapy

A strategy combining covalent conjugation of photosensitizers to a peptide ligand directed to the melanocortin 1 (MC1) receptor with the application of sequential LED light dosage at near-IR wavelengths was developed to achieve specific cytotoxicity to melanocytes and melanoma (MEL) with minimal collateral damage to surrounding cells such as keratinocytes (KER). The specific killing of melanotic cells by targeted photodynamic therapy (PDT) described in this study holds promise as a potentially effective adjuvant therapeutic method to control benign skin hyperpigmentation or superficial melanotic malignancy such as Lentigo Maligna Melanoma (LMM).