AN APPLICATION OF ORGANIC PHOSPHORUS COMPOUNDS IN THE PEPTIDE AND NUCLEOTIDE SYNTHESIS

Abstract

Organic trivalent phosphorus compounds, such as trialkyl phosphites and trialkyl- or triarylphosphines, are well known to be powerful deoxygenation reagents and have been used in various reduction reactions; for example, as illustrated in the following reactions developed in our laboratory.¹⁻³ However it is rather a new aspect to make use of their deoxygenative property for the generation of active acyl groups. Since the discovery of the reaction of mercuric acetate with trivalent phosphorus compounds to yield acetic anhydride,

our attention has been focused on the generations of acyl groups, and several novel reactions have been found which are applicable to the preparation of acid anhydride, peptide, and nucleotide linkages. In considering these reactions described herein, it is necessary to choose appropriate oxidation reagents together with reducing reagents (trivalent phosphorus compounds), because these dehydration reactions essentially proceed viu an oxidation-reduction process as depicted in the following scheme.