Synthesis, Formation Mechanism And Properties Of Pentacoordinated Spirophosphoranes Derived From Amino Acids

Pentacoordinated spirophosphoranes derived from amio acids are very important in organic phosphorus chemistry and biological chemistry. N-phospho-α-amio acids are obtained by phospholation of amio acids, and they can take place many kinds of bioorganic reactions in water/alcohol media. For example, peptide formation, the ester formation, the ester exchange on phosphorus and N O phosphoryl migration reactions are observed. The synthesis of peptide is one of the most crucial reactions in origin of life. And then the peptide formation from N-phospho-α-amio acids plays a significant role in the model of the coevolution of protein and nucleotides. Hence, it is very important to study the synthesis and reactivity of the pentacoordinated spirophosphoranes containing amino acid moiety. To obtain the unambiguous structure characterization is not only important for comprehending the biosynthesis of proteins but also for the study origin of life.In this thesis, the synthesis, physic and chemical characters, the bioactivity and the reaction mechanism were studied with assistance of NMR, ESI-MS, X-ray diffraction and theoretical chemistry technology. The results are illustrated as following:Two types of amino acid spirophosphoranes were synthesized. The products were characterized by using many kinds of technology. The method is very simple and convenient with reasonable yield. To study the mechanism, the reaction was traced by 31P NMR spectroscopy. It was found that onlyα-amino acids could be converted into spirophosphoranes...