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Selectivity in abiotic condensations of amino acids remains controversial and stereochemically little explored. We find that competitive activated couplings of N-acyl derivatives of glycine, alanine, valine, proline and phenylalanine with binary, ternary and quaternary mixtures of amides and esters of the same group of amino acids show little selectivity among the reactants, except with respect to configuration, where a consistent and significant preference for heterochiral outcomes, mostly > 80%, is observed. One possible explanation of this selectivity predicts a predisposition to homochiral coupling under conditions that would require the two carboxyl functions to be co-facial in the activated complex.
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Graham E Jeffs, and
Michael North
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Roger R Hill, and
David Birch, and
Graham E Jeffs, and
Michael North
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Science (New York, N.Y.),
Roger R Hill, and
David Birch, and
Graham E Jeffs, and
Michael North
May 2008,
Chemistry & biology,
Roger R Hill, and
David Birch, and
Graham E Jeffs, and
Michael North
September 1949,
Federation proceedings,
Roger R Hill, and
David Birch, and
Graham E Jeffs, and
Michael North
January 1995,
Progress in nucleic acid research and molecular biology,
Roger R Hill, and
David Birch, and
Graham E Jeffs, and
Michael North
June 2021,
Angewandte Chemie (International ed. in English),
Roger R Hill, and
David Birch, and
Graham E Jeffs, and
Michael North
September 1969,
The Biochemical journal,
Roger R Hill, and
David Birch, and
Graham E Jeffs, and
Michael North
January 2001,
Science (New York, N.Y.),
Roger R Hill, and
David Birch, and
Graham E Jeffs, and
Michael North
January 2001,
Science (New York, N.Y.),
Roger R Hill, and
David Birch, and
Graham E Jeffs, and
Michael North
September 2002,
Proceedings of the National Academy of Sciences of the United States of America,
