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Download Bioorganic Chemistry: A Chemical Approach to Enzyme Action by Hermann Dugas PDF

By Hermann Dugas

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Extra info for Bioorganic Chemistry: A Chemical Approach to Enzyme Action

Sample text

Further, due to the excellent nucleophilicity of the sulfur atom, such compounds are readily prepared, as is illustrated in the following model reaction: E9/ CH 3 Ph-S I ,--------: 0-- CH Nu ~ nucleophile E9 Ph-S-CH 3 + CH 3-Nu In biological systems, the universal methyl group donor is the sulfonium compound S-adenosyl methionine (SAM). In turn this is synthesized from the amino acid methionine and another biologically important compound (a "high-energy" compound or biological energy store) adenosine triphosphate (ATP).

CI .. +H N-R' 2 ------+ o I R-C-NH-R' + HCI '"-v---' peptide bond formation Within the biological context, an anhydride structure, as indicated below, is a high-energy structure or potential energy store. The definition of high- o II •• Z I (-C-X-y-) energy for biological systems and more background into the chemistry of anhydrides is presented in Chapter 3 on bioorganic phosphorus. 0 kcaljmol). Examples include acetic anhydride, acetyl phosphate, and acetyl imidazole. The biological energy store ATP also possesses the anhydride structure in its triphosphate side o I 0 I CH3-C-0-C-CH3 acetic anhydride acetyl phosphate acetyl imidazole chain.

CH 3 " N /CH 3 ~ yv dansyl chloride dabsyl chloride One reaction type that merits special consideration is the acylation of amino acids. Other reactions of the amino acids are biologically important. For example, it will be seen later that it is Schiff base formation of the amino function with an aldehyde that provides the basis for all reactions with vitamin B6 (see Chapter 7). However, it is acylation of the amino function of one amino acid with the carboxyl (activated) of another amino acid that leads to formation of the peptide bond and subsequent protein, or polymer formation.

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