An efficient route towards a new branched tetrahydrofurane δ-sugar amino acid from a pyrolysis product of cellulose

Amino Acids
Andrea DefantDaniele Fabbri

Abstract

(1R,5S)-1-hydroxy-3,6-dioxa-bicyclo[3.2.1]octan-2-one, is a bicyclic lactone obtained in gram-scale by catalytic pyrolysis of the renewable source cellulose. Now it has been used as a chiral building block in the preparation of the new δ-sugar amino acid, (3R,5S)-5-(aminoethyl)-3-hydroxytetrahydrofurane-3-carboxylic acid, by an efficient synthesis in five steps with a 67% overall yield. The structure of this tetrahydrofurane amino acid, isolated in protonated form, was assigned by extensive mono- and bidimensional (1)H- and (13)C-NMR analysis and mass spectrometry, including measurements by electrospray and matrix-assisted laser desorption ionization techniques, the latter one for high-resolution experiments. This amino acid is an isoster of dipeptide glycine-alanine (H-Gly-Ala-OH), with a potential use in the access of new peptidomimetics with conformationally restricted structures due to the presence of tetrahydrofurane ring. As a preliminary study in order to disclose this effect, density functional theory calculation performed in water using polar continuum model was applied to the new amino acid and H-Gly-Ala-OH dipeptide, so that to evaluate and compare the relative torsional angles for the energy-minimized structures.

References

Jan 1, 1997·Annual Review of Physical Chemistry·C L Perrin, J B Nielson
Dec 2, 1999·Journal of Peptide Science : an Official Publication of the European Peptide Society·M D Smith, G W Fleet
Feb 14, 2002·Chemical Reviews·Sibylle A W GrunerHorst Kessler
Mar 9, 2004·Journal of Combinatorial Chemistry·Alison A EdwardsGeorge W J Fleet
Dec 21, 2006·Journal of the American Chemical Society·Rebecca A JockuschJohn P Simons

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Citations

Sep 20, 2016·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Tainah Dorina MarforioFrancesco Zerbetto
May 15, 2015·Organic & Biomolecular Chemistry·Andrea DefantDaniele Fabbri

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