Research

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


Reference:

Beauchard, A., Twum, E. A., Lloyd, M. D. and Threadgill, M. D., 2011. S-2-Amino-4-cyanobutanoic acid (β-cyanomethyl-L-Ala) as an atom-efficient solubilising synthon for L-glutamine. Tetrahedron Letters, 52 (41), pp. 5311-5314.

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    Official URL:

    http://dx.doi.org/10.1016/j.tetlet.2011.08.017

    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.

    Details

    Item Type Articles
    CreatorsBeauchard, A., Twum, E. A., Lloyd, M. D. and Threadgill, M. D.
    DOI10.1016/j.tetlet.2011.08.017
    DepartmentsFaculty of Science > Pharmacy & Pharmacology
    Publisher StatementThreadgill_Tetrahedron_Letters_2011_52_41_5311.pdf: NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron Letters. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron Letters, vol 52, issue 41, 2011, DOI 10.1016/j.tetlet.2011.08.017; Threadgill_Tetrahedron_Letters_2011_52_41_5311.doc: NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron Letters. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron Letters, vol 52, issue 41, 2011, DOI 10.1016/j.tetlet.2011.08.017
    RefereedYes
    StatusPublished
    ID Code28015

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