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Title: Studies in peptide synthesis
Author: Williams, M. W.
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 1961
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One of the most important considerations in peptide synthesis is the avoidance of loss of optical activity at the asymmetric centres of the amino-acids when these are condensed together. This racemisation is undesirable not only because it limits the yield of required product but also because the presence of even traces of racemates or disaster- eoisomers may inhibit crystallisation of a peptide, thus rendering purification more difficult. The most commonly employed amino protecting group, the benzyloxycarbonyl group, confers a remarkable optical stability upon the amino-acid which it protects, and the observation that a benzyloxycarbonyl amino-acid may be coupled without danger of racemisation under conditions which may cause considerable loss of activity when the benzyloxycarbonyldi- peptide, so formed, is coupled further, led to a much greater awareness of the problem. Thus, in 1955, North and Young initiated a study of coupling reactions from the point of view of racemisation, using the condensation of acetyl- L-leucine with glycine ester as a model reaction. They found that the azide procedure was remarkably free from the danger of racemisation but other procedures, including those which have been postulated to involve amino-activation, may result in considerable loss of activity.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available