Bioorganic Chemistry of the Amino Acids

Abstract

Bioorganic chemistry provides a link between the work of the organic chemist and biochemist, and this chapter is intended to serve as a link between organic chemistry, biochemistry, and protein and medicinal chemistry or pharmacology. The emphasis is chemical and one is continually reminded to compare and contrast biochemical reactions with mechanistic and synthetic counterparts. The organic synthesis and biosynthesis of the peptide bond and the phosphate ester linkage (see Chapter 3) are presented “side-by-side”; this way, a surprising number of similarities are readily seen. Each amino acid is viewed separately as an organic entity with a unique chemistry. Dissociation behavior is related in terms of other organic acids and bases, and the basic principles are reviewed so that one is not left with the impression of the amino acid as being a peculiar species. The chemistry of the amino acids is presented as if part of an organic chemistry text, (alkylations, acylations, etc.), and biochemical topics are then discussed in a chemical light.

“L’ imagination est plus importante que le savoir.”

A. Einstein