The Synthesis and Structure of Threonine: Herbert E. Carter
Year: 2002
Type: article
Abstract: Synthesis of α-Amino-β-hydroxy-n-butyric Acids (Carter, H. E. (1935) J. Biol. Chem. 112, 769–773) As reported in a previous Journal of Biological Chemistry (JBC) Classic (1JBC Classics Rose W.C. J. Biol. Chem. 1931; 94: 155-165Google ScholarMcCoy R.H. Meyer C.E. Rose W.C. J. Biol. Chem. 1935; 112 (http://www.jbc.org/cgi/content/full/277/37/e25): 283-302Abstract Full Text PDF Google Scholar), William C. Rose and his colleagues at the University of Illinois discovered the amino acid threonine as the twentieth of the amino acids that are universal components of proteins. As also reported by Rose (1JBC Classics Rose W.C. J. Biol. Chem. 1931; 94: 155-165Google ScholarMcCoy R.H. Meyer C.E. Rose W.C. J. Biol. Chem. 1935; 112 (http://www.jbc.org/cgi/content/full/277/37/e25): 283-302Abstract Full Text PDF Google Scholar), they did not determine which isomer of threonine is the naturally occurring amino acid. Considering that threonine, α-amino-β-hydroxy-n-butyric acid, has two asymmetric carbons and thus four possible optical isomers, it was possible that one or more isomers might have satisfied the dietary requirement for threonine in the rats that Rose used as an assay. Herbert E. Carter, the author of this JBC Classic, was born in 1910. He received the A.B. degree from DePauw University in 1930 and M.S. and Ph.D. degrees in organic chemistry from the University of Illinois in 1931 and 1934, respectively. Although working for his Ph.D. with Professor C. S. Marvel in the chemistry department, Carter was prevailed upon by Rose to define the structure of the naturally occurring threonine that he had isolated. In 1934, Carter was appointed Assistant Professor of Biochemistry, a division within the chemistry department that Rose chaired, and was assigned to identify the isomeric form of this newest constituent of proteins. The results of Carter's first research project after his Ph.D. thesis work are reported in this JBC Classic, the first of a series of seven papers that ultimately demonstrate the structure of threonine as it occurs in nature. The experimental plan was to synthesize relevant model molecules and to determine and/or deduce the isomeric structures that had been produced. The mixtures of synthetic products were tested in the rat nutrition assay to determine whether or not they could replace the natural, isolated amino acid. Using the method of Abderhalden and Heyns (2Abderhalden E. Heyns K. Ber. Chem. Ges. 1934; 67: 530Crossref Google Scholar), Carter preparedα -amino-β-hydroxy-n-butyric acid and found that it did not support the growth of rats. Reasoning that this method yielded only one possible isomer, he converted the inactive form into the two possible epimers that did support growth. This work by Carter and his co-workers exemplifies an important general approach to the elucidation of structures of naturally occurring compounds that was widely used, i.e. the synthesis and evaluation of biological functions of candidate molecules. Following his appointment as Assistant Professor of Biochemistry in 1934, Carter had a long and distinguished career at the University of Illinois in Urbana. He rose through the academic ranks to Professor by 1945 and was Head of the Department of Chemistry and Chemical Engineering from 1954 to 1967. He also served as Vice Chancellor for Academic Affairs. In 1971, he moved to the University of Arizona as Coordinator of Interdisciplinary Programs where he continues to be active. Carter has made many important contributions, particularly in antibiotic chemistry and the biochemistry of complex lipids. In the latter area, he determined the structure of sphingosine and cerebrosides and identified novel lipids in plants including phytosphingosine, phytoglycolipids, and galactosylglycerides. Carter received many honors for his research, including election to the National Academy of Sciences in 1953. He was a member, and then chairman, of the National Science Board, and in recognition of his chairmanship, a mountain ridge in Antarctica, “Carter Ridge,” has been named. He served also as Chairman of the President's Committee on the National Medal of Science. He is a past President of the American Society of Biological Chemists. 1We thank Professor Carter for providing biographical information for this introduction to his Classic paper. 1We thank Professor Carter for providing biographical information for this introduction to his Classic paper.
Source: Journal of Biological Chemistry
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $3,430
OpenAlex ID: W1511071827