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Sensing the anomeric effect in a solvent-free environment

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  • Emilio J. Cocinero

    (Physical and Theoretical Chemistry Laboratory, University of Oxford
    Present addresses: Departamento de Quimica Fisica, Facultad de Ciencia y Tecnologia, Universidad del Pais Vasco (UPV-EHU), Apartado 644, E-48940, Bilbao, Spain (E.J.C.); Institut des Sciences Moleculaires d’Orsay ? CNRS, Universite Paris Sud, F91405 Orsay Cedex, France (P.C.); Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Road, Glassboro, New Jersey 08028, USA (T.D.V.).)

  • Pierre Carcabal

    (Physical and Theoretical Chemistry Laboratory, University of Oxford
    Present addresses: Departamento de Quimica Fisica, Facultad de Ciencia y Tecnologia, Universidad del Pais Vasco (UPV-EHU), Apartado 644, E-48940, Bilbao, Spain (E.J.C.); Institut des Sciences Moleculaires d’Orsay ? CNRS, Universite Paris Sud, F91405 Orsay Cedex, France (P.C.); Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Road, Glassboro, New Jersey 08028, USA (T.D.V.).)

  • Timothy D. Vaden

    (Physical and Theoretical Chemistry Laboratory, University of Oxford
    Present addresses: Departamento de Quimica Fisica, Facultad de Ciencia y Tecnologia, Universidad del Pais Vasco (UPV-EHU), Apartado 644, E-48940, Bilbao, Spain (E.J.C.); Institut des Sciences Moleculaires d’Orsay ? CNRS, Universite Paris Sud, F91405 Orsay Cedex, France (P.C.); Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Road, Glassboro, New Jersey 08028, USA (T.D.V.).)

  • John P. Simons

    (Physical and Theoretical Chemistry Laboratory, University of Oxford)

  • Benjamin G. Davis

    (Chemistry Research Laboratory, University of Oxford)

Abstract

The anomeric effect: C2 in the ring The anomeric effect is a chemical phenomenon that refers to an observed stabilization of six-membered carbohydrate rings when they contain an electronegative substituent at the C1 position of the ring. This stereo-electronic effect influences the three-dimensional shapes of many biological molecules, but its underlying physical origin is still not clear. Cocinero et al. use a combination of laser spectroscopy and computational analysis to create a peptidic sensor that can bind the archetypal carbohydrate D-galactose in two different anomeric forms. Complexes formed between the truncated peptide motif and isolated D-galactose in the gas phase are nearly identical structurally, although the strength of the polarization of their interactions with the peptide differs greatly. These results suggest that it will be important to re-evaluate the influence, and biological effects, of substituents at the C2 position of the six-membered carbohydrate rings.

Suggested Citation

  • Emilio J. Cocinero & Pierre Carcabal & Timothy D. Vaden & John P. Simons & Benjamin G. Davis, 2011. "Sensing the anomeric effect in a solvent-free environment," Nature, Nature, vol. 469(7328), pages 76-79, January.
    • Handle: RePEc:nat:nature:v:469:y:2011:i:7328:d:10.1038_nature09693
    DOI: 10.1038/nature09693
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