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Related Experiment Videos

Activity difference between alpha-COOH and beta-COOH in N-phosphorylaspartic acids.

Zhong-Zhou Chen1, Bo Tan, Yan-Mei Li

  • 1Key Laboratory for Bioorganic Phosphorus Chemistry of Education Ministry, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.

The Journal of Organic Chemistry
|May 10, 2003
PubMed
Summary

N-phosphorylamino acids show biomimic activity. N-phosphorylation selectively activates the alpha-COOH group in N-phosphorylaspartic acid, facilitating direct peptide formation without coupling reagents.

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Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Computational Chemistry

Background:

  • N-phosphorylamino acids exhibit biomimic activities, with alpha-carboxyl (COOH) groups playing a crucial role in biochemical processes and the origin of life.
  • Understanding the differential reactivity of alpha-COOH versus beta-COOH in these molecules is key to elucidating their biological functions.

Purpose of the Study:

  • To investigate the distinct activities of alpha-COOH and beta-COOH in the peptide formation of phosphoryl amino acids.
  • To determine the preferred site of activation upon N-phosphorylation in aspartic acid.

Main Methods:

  • Utilized 1D and 2D Nuclear Magnetic Resonance (NMR) spectroscopy (1H, 13C, 31P) for experimental analysis.
  • Employed ab initio and Density Functional Theory (DFT) calculations for theoretical investigations.

Related Experiment Videos

  • Studied direct phosphoryl dipeptide formation from phosphoryl aspartic acids without coupling agents.

    • Main Results:

    • Direct formation of phosphoryl dipeptides from phosphoryl aspartic acids was observed without coupling reagents.
    • Experimental NMR data exclusively identified the alpha-dipeptide ester.
    • Theoretical calculations predicted pentacoordinate phosphorane intermediates with five-membered rings to be more stable than those with six-membered rings.

    Conclusions:

    • N-phosphorylation selectively activates the alpha-COOH group in N-phosphorylaspartic acid under mild conditions.
    • Both experimental and theoretical findings consistently support the preferential activation of the alpha-COOH group.
    • This selective activation mechanism is crucial for understanding peptide bond formation in N-phosphorylated amino acids.