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Bailey peptide synthesis

Organic chemistry From Wikipedia, the free encyclopedia

Bailey peptide synthesis
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The Bailey peptide synthesis is a name reaction in organic chemistry developed 1949 by J. L. Bailey.[1][2] It is a method for the synthesis of a peptide from α-amino acid-N-carboxylic acid anhydrides (NCAs) and amino acids or peptide esters.[2][3] The reaction is characterized by short reaction times and a high yield of the target peptide.[2]

The reaction can be carried out at low temperatures in organic solvents.[2] The residues R1 and R2 can be organic groups or hydrogen atoms, R3 is the used amino acid or peptide ester:[2]

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Übersichtsreaktion der Bailey-Peptid-Synthese
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Reaction mechanism

The reaction mechanism is not known in detail. Supposedly, the reaction begins with a nucleophilic attack of the amino group on the carbonyl carbon of the anhydride group of the N-carboxylic acid anhydride (1). After an intramolecular proton migration, a 1,4-proton shift and the cleavage of carbon dioxide follows, resulting in the peptide bond in the final product (2):[2]

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Übersichtsreaktion der Bailey-Peptid-Synthese
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Atom economy

The advantage in atom economy of using NCAs for peptide formation is that there is no need for a protecting group on the functional group reacted with the amino acid.[4] For example, the Merrifield synthesis depends on the use of Boc and Bzl protecting groups, which need be removed after the reaction.[5] In the case of Bailey peptide synthesis, the free peptide is directly obtained after the reaction.[4] However, unwanted and difficult to remove by-products may be formed.[4] An N-substitution of the NCA (for example, by an o-nitrophenylsulfenyl group) can simplify the subsequent purification process, but on the other hand deteriorates the atom economy of the reaction. [4] The synthesis of NCAs can be carried out by the Leuchs reaction[6] or by the reaction of N-(benzyloxycarbonyl)-amino acids with oxalyl chloride.[7] In the latter case, again the procedure is less efficient in the sense of atom economy.

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Synthesized peptides

The following peptides were synthesized using this method by 1949:[3]

Literature

  • P. Katsoyannis: The Chemistry of Polypeptides. Springer Science & Business Media, 2012, ISBN 978-1-461-34571-8, S. 129.

References

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