The reduction of esters of simple peptides by metal hydrides

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Abstract
[beta]-Hydroxyamides corresponding to a number of peptide esters and their toluene-p-sulfonyl derivatives were prepared. Quantitative reduction of ester groups with lithium aluminum hydride (LiAlH4) was impossible in many cases owing to the formation of insoluble aluminium complexes. Both LiAlH4 and aluminium hydride (AlH3) reduce the peptide bond. Greater control of the reaction is possible with the latter reagent. Lithium borohydride (LiBH4) is the most suitable reagent for reducing peptide esters. Homogenous reaction mixtures are usually obtained and the minimum of side reactions take place.

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