Date of Award

6-1971

Document Type

Union College Only

Degree Name

Bachelor of Science

Department

Chemistry

Language

English

Abstract

The formation of a carbamate on hemoglobin is one method proposed for carbon dioxide transport in the blood. As of yet, no direct method has been reported for quantitatively determining to what extent carbamate formation occurs. The phosphorescence of glycine carbamate is of interest in this problem. Glycine is structurally similar to the globin endings, so that it presents a model that is simpler and more easily studied but still contains a sufficient degree of similarity to hemoglobin for the purpose of studying this reaction. Phosphorescence spectroscopy has been proposed a possible method for direct quantitative analysis of glycine carbamate. To gain information about the contribution of the various substituents, it was decided that N-carbomethoxy glycine, N-carbomethoxy glycine methylester, and N-carbomethoxy- N-methyl glycine should be synthesized so that they could be checked for any change in phosphorescence from glycine carbamate. The diesters were synthesized by condensation of the appropriate amino acid methylester in the case of N-carbomethoxy glycine methylester and amino acid in the case of the N-methyl carbamate with methyl chloroformate. The N-carbomethoxy-N-methyl glycine was converted through esterification with methanol to the methyl ester. Both products were successfully synthesized and purified. Synthesis of N-carbomethoxy glycine was attempted by saponification of the methyl ester as reported by Petri and Staverman. (1) No product has been obtained yet due to problems in separation. Both products obtained showed phosphorescence consistent with the phosphorescence spectrum obtained for glycine carbamate. Identification was substantiated with infrared and nuclear magnetic resonance spectroscopy. Purity was determined by thin layer chromatography.

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