S-2-Amino-4-cyanobutanoic acid (β-cyanomethyl-L-Ala) as an atom-efficient solubilising synthon for L-glutamine

Anne Beauchard, Elvis A Twum, Matthew D Lloyd, Michael D Threadgill

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Abstract

Glutamine (Gln) is often a difficult amino acid to incorporate during solution-phase peptide synthesis, owing to poor solubility and unwanted dehydrations as side-reactions. Current approaches to solving these problems are highly atom-inefficient. N(alpha)-Cbz-beta-cyanomethyl-L-Ala is readily accessible by dehydration of Cbz-L-Gln. beta-Cyanomethyl-L-Ala can be incorporated into short peptides easily by conventional methods. The nitrite is stable to the hydrogenolysis conditions used to remove Cbz and to acidic deprotection but is quantitatively hydrated to the gamma-carboxamide of L-Gln with hydrogen peroxide. Thus beta-cyanomethyl-L-Ala may represent a new, soluble, perfectly atom-efficient synthon for L-Gln.
Original languageEnglish
Pages (from-to)5311-5314
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number41
DOIs
Publication statusPublished - 12 Oct 2011

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