The Chemical Synthesis of Peptides

Curtius (1881) and Fischer (1902) were the first to synthesize simple peptide derivatives (2:1-8). About that time, Hofmeister (1902) and Fischer (1906) additionally recognized that proteins actually consist of amino acids linked together by amide bonds. Subsequent peptide research generally involved the synthesis of "small, well-defined peptides" which were used to study certain proteolytic enzymes (2:1-8).

Around the mid-20th century, researchers discovered biologically active peptides. Oxytocin was isolated in 1952. Shortly thereafter, investigators (du Vigneaud et al. 1953, Tuppy 1953) determined oxytocin's structure. In fact, the total synthesis of polypeptide (du Vigneaud et al. 1953) eventually helped motivate the development of more advanced synthetic procedures.

It wasn't until Sanger and associates (1953) demonstrated the structure of insulin, however, that the study of peptides became more pragmatic. Researchers recognized that they could synthesize significant qu

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hdrawing X-groups which can be used to create peptide bonds (2:9-14). In addition to electron-withdrawing groups, peptide synthesis also requires easily removable protecting groups. During synthesis, those amino groups and carboxyl groups which are not supposed to be part of the amide bond must be protected. Otherwise, the activated carboxyl-component (A) may acylate not only the amino-component (B), but also some unreacted molecules of A. Rather than produce the desired compound AB, such reactions would also produce a derivative AA. Furthermore, other products which may be created under such conditions might include a cyclic dipeptide AA, as well as peptides with sequences AAB, AAAB, and so on (2:63-74). The general process of protection may be described schematically as follows: Y-NH-CHR-CO-X + H2N-CHR'-COOY' -> Y-NH-CHR-CO-NH-CHR'-COOY' + HX The first easily removable protecting groups were discovered in 1932. Bergmann and Zervas (1932) found that benzyloxycarbonyl groups could be removed at room temperatures and pressures through catalytic hydrogenation (2:63-74). There are a number of different specific approaches to chemical peptide synthesis. For one, the most classical procedure may be the azide method. First de
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Approximate Word count = 2665
Approximate Pages = 11 (250 words per page)

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