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Enantioselection in peptide bond formation

Hill, Roger R.; Birch, David; Jeffs, Graham and North, Michael (2003). Enantioselection in peptide bond formation. Organic and Biomolecular Chemistry, 1(6) pp. 965–972.

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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.

Item Type: Journal Article
ISSN: 1477-0520
Extra Information: Some of the symbols may not have transferred correctly into this bibliographic record and/or abstract.
Keywords: aromatic interactions; origin; life; racemization; condensation; polypeptides; efficiency; emergence; alumina; proline
Academic Unit/Department: Science > Life, Health and Chemical Sciences
Item ID: 6159
Depositing User: Astrid Peterkin
Date Deposited: 05 Jan 2007
Last Modified: 02 Dec 2010 19:55
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