By Erhard Gross, Johannes Meienhofer

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38 Erhard Gross and Johannes Meienhofer carboxylic acids on the aminolysis of activated esters in dioxane were studied and reaction rates and activation enthalpies and entropies determined (Muzalewski, 1973). General acid catalysis of ester aminolysis by carboxylic acids is most effective in nonpolar solvents such as tetrahydrofuran and negligible in dimethylformamide. , p-nitrophenyl and 2,4,5-trichlorophenyl esters in polar solvents such as dimethylformamide and dimethylacetamide, presumably via intermediate addition complexes (structure 10, Scheme 15), see König N R-COO- N 0 2 + H 2 NR' + > (9) OH R' H i NO, ^ 1 0 ,Ν (10) N RCO-NHR' + HO NO, + HOBt Scheme 15 and Geiger (1972, 1973a,b).

In its 15 years of development, the solid phase method has provided enormous and unprecedented stimuli to peptide synthesis and has been used to prepare hundreds of peptides of varying sizes and functions. The most remarkable achievement has been the synthesis of a ribonuclease A preparation with 78 % of the activity of the native enzyme (Gutte and Merrifield, 1969, 1971). The main attractive features of the method are: (a) high speed, permitting up to six amino acid residues to be coupled per day, (b) no insolubility problems of the kind that hamper solution synthesis, (c) ease and convenience of operation, and (d) mechanization and automation.

The preservation of chiral integrity during coupling is a cardinal criterion for judging the relative merits of synthetic methods. 1% (Izumiya et al, 1971) of Denantiomer have become available in recent years. The carboxyl component is mainly at risk, since both its preparation and its subsequent use in coupling may lead to 5(4H)-oxazolone formation (compound 12a, Scheme 19) which constitutes the main pathway of peptide racemization (see Kemp, (12a) Scheme 19 this volume, Chapter 7). Another significant racemization mechanism involves hydrogen abstraction from the α-carbon followed by enolization (Scheme 20) (Goodman and Glaser, 1970; Kemp and Rebek, 1970).

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