I. The Benzylation of Carbohydrates. II. The Preparation of Fluorinated Analogues of Tyrosine and Thyronine. III. The Preparation of Isomers and Analogues of Thyroxine with Relation to a Proposed Hypothesis of the Relationship Between Structure and Thyroxine-Like Activity. IV. A Carotenoid from Bovine Spinal Cord. V. Studies on the Structure of Sphingosine. VI. The Length Muscles of the Holothurians (a Summary)

Citation

Mead, James Franklyn (1942) I. The Benzylation of Carbohydrates. II. The Preparation of Fluorinated Analogues of Tyrosine and Thyronine. III. The Preparation of Isomers and Analogues of Thyroxine with Relation to a Proposed Hypothesis of the Relationship Between Structure and Thyroxine-Like Activity. IV. A Carotenoid from Bovine Spinal Cord. V. Studies on the Structure of Sphingosine. VI. The Length Muscles of the Holothurians (a Summary). Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/MND7-0F42. https://resolver.caltech.edu/CaltechTHESIS:10062017-104405641

Abstract

Part I

A new method for the determination of the structure of polysaccharides has been proposed. A method for the benzylation of sugars has been found, since the benzylation of the polysaccharides is necessary as the first step in the proposed method.

Part II

In connection with the physiological action of organic fluorine compounds, a number of fluorinated amino acids have been prepared. The synthesis of 3-fluoro-dl-tyrosine, 3-fluoro-5-iodo-dl-tyrosine, 3-fluoro-dl-phenlalanine, 3'-fluoro-dl-thyronine, 3'-fluoro-3,5- diiodo-dl-thyronine and 3'-fluoro-5'-iodo-3,5-diiodo-dl-thyronine has been described.

In connection with the synthesis of 3,5-difluoro-dl-thyronine, the preparation of the necessary starting materials has been described.

Part III

The synthesis of dl-3,5-diiodo-4-(3',5'diiodo-2'-hydroxy-phenoxy)-phenylalanine, an isomer of thyroxine, is described. This compound is physiologically active, the activity being approximately one twenty-fifth of that of dl-thyroxine. This finding is in accordance with a prediction relating thyroxine-like activity to chemical structure.

The attempted synthesis of dl-diiodo-4-(3',5'-diiodo-4'- aminophenoxy)-phenylalanine is described.

Part IV

The separation of the carotenoid, β-carotene, from bovine spinal cord is described.

Part V

The separation of large amounts of cerebrodise-sphinogomylin fraction from bovine spinal cord is described. The separation of sphingosine and sphingosine derivatives, and reactions proposed to lead to a determination of the structure of sphingosine are given.

Thesis Files