Since B-aminoethylphosphonic acid was discovered in the living organism, the biosynthesis and biological function of aminophosphonic acids have been extensively studied.
The purpose of this project consists in the two parts: 1)the preparation of DL-1-amino- 2-phenylethylphosphonic acid (Phenylalanine aminophosphonic acid) and DL-1-amino-3-methylbutyl-phosphonic acid (Isoleucine aminophosphonic acid) by the method of Chamber and Isbell. 2) the study of metabolism and biological functions of those synthetic materials by the animal experiment (white rats)
The importance of this project proved to be the first experience fed by animals for the elucidation of biochemical and metabolic functions in the animal body.
The following organic synthesis of DL-1-amino-3-methylbutylphosphonic acid and DL-1-amino-2-phenylethylphosphonic acid are studied.
1)Synthesis of DL-1-amino-3-methylbutylphosphonic acid
a) Synthesis of Iso-butylbromide
b) Synthesis of Ethyl iso-butylmalonate
c) Synthesis of Iso-caproic acid
d) Synthesis of Ethyl-a-bromo iso-caproate
e) Synthesis of Triethyl-a-phosphono iso-caproate
f) Synthesis of DL-1-amino-3-methylbutylphosphonic acid
2)Synthesis of DL-1-amino-2-phenvlethylphosphonic acid
a) Synthesis of Diethyl phosphite
b) Synthesis of Ethylchloro acetate
c) Synthesis of Triethyl phospho acetate
d) Synthesis of Triethyl benzyl phospho acetate
e) Synthesis of DL-1-amino-2-phenylethylphosphonic acid
The synthetic compounds; DL-1-amino-3-methylbutylphosphonic acid and DL-1-amino-2-phenyl ethylphosphonic acid which are essential amino acid (isoleucine, phenylalanine)analogue are supplemented to the animal diet at the level of 0.2 % and 0.4 o for isoleucine analogue and 0.35 5% and 0. 7,% for phenylalanine analogue.
The plain isoleucine and phenylalanine at the same level in the diet are fercilitated as comparable groups
in this study.
Two sets of experience including 100 male rats were carried out for seven weeks each total 14 weeks-During this, period, urine samples, and each big organs were collected for the analysis of total nitrogen, phosphorus, and glycogen contents in the individual samples by Micro Kjeldahl1´i Fisk & Subbarow"I and Nelson Somogyell 1s- method.
1) The result of the project
a) The yield of DL-1-amino-3-methylbutylphosphonic acid and DL-1-amino-2-phenylethylphosphonic acid showed low tendency at the level of 12.5". and 20% Melting point of those two compounds were very high and the a-amino group in the synthetic compounds showed positive reaction with ninhvdrin in the violet color.
b) All the experimental groups included in this study revealed statistically no significant difference in the organ weight, total body nitrogen retention and urinary phosphorus excretion This means isoleucine aminophosphonic acid and Phenylalanine aminophosphonic acid were utilized in the body as much as the plain amino acids, isoleucine and phenylalanine did.
c) The glycogen contents in the liver of the phenylalaine aminophosphonic acid gruop showed higher statistically significant (p>0.05) in the comparision with the group of the Phenylalanine and the Standard-2.
It was noteworthy that the higher glycogen content in the liver might indicate the significance in the incorporation of Phenylalanine aminophosphonic acid into the intermediate of tricarboxylic acid cycle as activated state.
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