Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2008 May;108(5):1708-31.
doi: 10.1021/cr078215f. Epub 2008 May 2.

The chemical neurobiology of carbohydrates

Heather E Murrey  1 , Linda C Hsieh-Wilson
Affiliations
Review

The chemical neurobiology of carbohydrates

Heather E Murrey et al. Chem Rev. 2008 May.
No abstract available

PubMed Disclaimer

Figures

Figure 1
Figure 1
Common structures of sialic acid derivatives: neuraminic acid (Neu), N-acetylneuraminic acid (Neu5Ac), N-glycolylneuraminic acid (Neu5Gc), and deaminoneuraminic acid (KDN).
Figure 2
Figure 2
Structures of gangliosides that bind to MAG. Neu5Ac = N-acetylneuramic acid; Gal = galactose; GalNAc = N-acetylgalactosamine; Glc = glucose; Cer = ceramide.
Figure 3
Figure 3
Synthetic sialic acid analogues tested for binding to MAG. Positions important for MAG interactions are shown in red.
Figure 4
Figure 4
Structure of (A) a potent disialyl MAG inhibitor and (B) a simplified mimic of the ganglioside GQ1bα with enhanced binding affinity to MAG relative to Neu5Acα(2–3)Galβ(1–3)-GalNAc.
Figure 5
Figure 5
(A) Mannosamine derivatives used for metabolic labeling (R = H or Ac) and (B) chemoselective labeling reaction after treatment of cells with ManLev (R = biotin).
Figure 6
Figure 6
Structures of various fucose derivatives and 2-dGal.
Figure 7
Figure 7
Inhibition of Fucα(1–2)Gal linkages with 2-dGal leads to stunted neurite outgrowth in hippocampal neurons cultured for 4 days in vitro (DIV). D-Gal is able to rescue the effects of 2-dGal. 3-dGal has no effect. White bar indicates 45 μm. Images courtesy of C. Gama.
Figure 8
Figure 8
Chemical probe for imaging lectin receptors (top) and staining of hippocampal neurons in culture (bottom panels) with the probe demonstrating the presence of Fucα(1–2)Gal lectins along the cell body and neurites. Cells were treated with 3 mM of the imaging probe (A) or biotin (B), labeled with a streptavidin–dye conjugate, and imaged by fluorescence microscopy. Images courtesy of C. Gama.
Figure 9
Figure 9
O-GlcNAc glycosylation.
Figure 10
Figure 10
(A) Chemoenzymatic approach for tagging O-GlcNAc glycosylated proteins, (B) UDP–azidogalactose probe for [3 + 2] cycloaddition chemistry using the chemoenzymatic approach, and (C) GlcNAz and biotin phosphine probe for metabolic labeling of O-GlcNAc-modified protein using the Staudinger ligation.
Figure 11
Figure 11
BEMAD approach for mapping O-GlcNAc glycosylation sites.
Figure 12
Figure 12
A fluorescence resonance energy transfer (FRET)-based sensor to detect O-GlcNAc glycosylation levels.
Figure 13
Figure 13
QUIC-Tag approach for quantifying dynamic changes in glycosylation.
Figure 14
Figure 14
Small-molecule OGA inhibitors.
Figure 15
Figure 15
Structures of GAG subclasses. Potential sulfation sites are indicated in red. R = SO3− or H; R1 = SO3−, H, or Ac; n = ~10–200.
Figure 16
Figure 16
CS-E, -A, -C, and -R tetrasaccharides. Only the CS-E tetrasaccharide promotes neurite outgrowth.
See this image and copyright information in PMC

References

    1. Becker DJ, Lowe JB. Glycobiology. 2003;13:41–53. - PubMed
    1. Gama CI, Hsieh-Wilson LC. Curr Opin Chem Biol. 2005;9:609–619. - PubMed
    1. Rampal R, Luther KB, Haltiwanger RS. Curr Mol Med. 2007;7:427–445. - PubMed
    1. Gabius HJ, Andre S, Kaltner H, Siebert HC. Biochim Biophys Acta. 2002;1572:165–177. - PubMed
    1. Nishihira J. Int J Mol Med. 1998;2:17–28. - PubMed

Publication types