CHEM564 Lecture Notes - Lecture 13: Hydrazine, Sulfur, Tetrahedron Letters

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We will be concerned with labeling biomolecules, and the issue of specificity will be a recurring problem. We may want to label a specific functional group (e. g. an amine), however in a biopolymer there may be many instances of this group. We will explore strategies for tackling this problem, and they will break down into two general areas: (1) exploitation of microenvironments or (2) introduction of, or use of unique functional groups. One could imagine that strategy (2) has some inherent advantages, but may face limitations in many situations. For example, cys-based reactivity is often the most commonly used strategy as the thiol group is easily differentiated from other common protein nucleophiles. However, if our protein of interest contains multiple. Cys residues, we are less likely to have site-specific control of the reaction (only functional- group control. ) In some situations this issue may not matter, however in other instances it may be critical.