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Extra info for Methods of Peptide Synthesis. The Peptides, Volume 1
Thiele and Dent (2307) used chloroform as solvent and carried out the reaction in a sealed tube at 60°-65°C. The compounds can be more readily obtained, ac cording to Carpenter and Gish (463), in dioxane at room temperature. p-Nitrocarbobenzoxy chloride is a stable crystalline compound. The blocked amino acids can be prepared by the standard procedures. The acid chloride is added in dioxane solution (463). The derivatives of serine, threonine, and tyrosine are best obtained in a dioxane-water mixture in the presence of equimolar amounts of alkali and sodium 32 I.
The same difficulties in purification and isolation are encountered. g. oxytocin or vasopressin). Birkhofer et al. (243) have described a decarbobenzoxylation by reduction with triethylsilane. It has been applied successfully to carbobenzoxy-S-benzylcysteine, with preservation of the S-benzyl protection. In addition to the protection of amino groups, phenolic hydroxyls (see Chapter IV,F,l,b,y) and the mercapto function (see Chapter IV, G,l,e) can also be blocked by the carbobenzoxy group. 2. Modified Carbobenzoxy Groups a.
This side reaction can be prevented by the addition of such compounds as phenol, resorcinol, or anisole that are very easily substituted. The reaction time varies from 12 to 150 minutes, depending on the amino acid used. Yields are 40-98%. g. O-benzyltyrosine) as well as benzyl esters. According to Khosla and Anand (1224b), decarbobenzoxylation occurs under even milder conditions (3 hours, 38°C). The benzyl, jo-nitrobenzyl, and methyl esters are cleaved in addition to the carbobenzoxy group, if a mixture of trifluoro acetic acid and hydrochloric acid is applied (4 hours, 40°C).