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.

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
Creators	Beauchard, A., Twum, E. A., Lloyd, M. D. and Threadgill, M. D.
DOI	10.1016/j.tetlet.2011.08.017
Departments	Faculty of Science > Pharmacy & Pharmacology
Publisher Statement	Threadgill_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
Refereed	Yes
Status	Published
ID Code	28015

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