I. An Investigation of the Dakin-West Reaction. II. The Role of Peroxides in Mutagenesis

Citation

Cleland, George Horace (1951) I. An Investigation of the Dakin-West Reaction. II. The Role of Peroxides in Mutagenesis. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/A274-DG11. https://resolver.caltech.edu/CaltechTHESIS:10062017-132951069

Abstract

An investigation of the Dakin-West reaction has been made, as a result of which the scope of the reaction has been extended in a number of ways.

a. It has been found that a number of aliphatic, aromatic and heterocyclic acid anhydrides, acyl fluorides, and (with the proper choice of catalysts) acid chlorides can be used in place of acetic anhydride in the reaction. Several cyclic anhydrides of dibasic acids have been shown not to react; in­conclusive results were obtained with maleic anhydride.

b. The reaction has been shown not to depend on a specific catalytic action of the pyridine structure, but to be cata­lyzed also by such bases as sodium acetate.

c. Several unusual α-amino acids have been shown to undergo the reaction; conclusions have been drawn as to the failure of several other amino acids to react. It has been shown that dipeptides can be used in place of amino acids.

d. A mechanism for the reaction has been proposed, based on evidence now available.

e. Observations have been made on side reactions of importance to the reaction; a method of utility for purifying the products of the reaction has been developed.

The role of peroxides in mutagenesis has been investigated; several peroxides have proved to be effective for the induction of mutations.

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