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Mechanism of intramolecular mixed anhydride formation as intermediates in the reactions of N-phosphorylamino-acids —An MNDO research

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Chinese Science Bulletin

Abstract

N-phosphoryl-α-amino acids can react to form esters, peptides, phosphoryl ester-exchanged products and phosphoryl group migration products under mild conditions, which are very important in researches on arohebiont. It has been proposed that intramolecular mixed carboxylic-phosphoric anhydrides (IMCPAs) might be the common intermediates of the reactions, which are difficult to be experimentally observed because of their high activity. In this note, it has been revealed, by means of MNDO, that the IMCPAs arc situated at the relatively minimal points of the potential surface and can form in a non-synchronous concerted reaction pathway that passes through a transition state with a hydrogen-bond-bridge structure. The results give a successful explanation to the structure and formation of IMCPAs and their ability to promote the various reactions mentioned above.

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Authors and Affiliations

  1. Bioorganic Phosphorus Chemistry Laboratory, Department of Chemistry, Tsinghua University, 100022, Beijing, China

    Zhong Rugang & Zhao Yufen

  2. Center for Chemistry and Bioengineering of Cancer Research, Beijing Polytechnic University, 100022, Beijing, China

    Zhong Rugang & Dai Qianhuan

Authors
  1. Zhong Rugang
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  2. Zhao Yufen
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  3. Dai Qianhuan
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Rugang, Z., Yufen, Z. & Qianhuan, D. Mechanism of intramolecular mixed anhydride formation as intermediates in the reactions of N-phosphorylamino-acids —An MNDO research. Chin. Sci. Bull. 43, 917–921 (1998). https://doi.org/10.1007/BF02884612

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  • DOI: https://doi.org/10.1007/BF02884612

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