Date of Award

2012

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Harp, Julius L. Dr.

Abstract

The primary objective of this research involves the synthetic design of homologs of 3, 4-dihydroxyphenylalanine (dopa) in order to inhibit melanin formation, melanogenesis. These synthetic homologs are structured to have variations within their side chains and unto their aromatic ring when compared to the structure of dopa. Strategic structural variations are incorporated within the molecular framework of the homologs such that their dopa mimicking features are enhanced, and consequently inhibit the formation of melanins. The structural variations of the homologs are designed to exhibit specificity in the regulations of phase-I and phase –II of melanogenesis. Many studies have suggested a strong correlation between enhanced rates of melanin formation and many forms of malignant melanomas (e.g., skin cancers). In this work, a variety of dopa precursors and dopa homologs were successfully synthesized. The synthetic methods developed for the preparation of the dopa homologs were also designed for efficient entry into a variety of new amino acids and precursors. Structural validation of dopa and precursors were aided by the use of a variety of instrumentations; inclusive of GC/MS, FTIR and NMR. The ultimate success of this work is expected to lead to the development of a more comprehensive profile between strategic molecular designs and melanin inhibition.

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