Cell surface engineering by a modified Staudinger reaction

Science

Volumn 287, Issue 5460, 2000, Pages 2007-2010

  Saxon, Eliana ^a   Bertozzi, Carolyn R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; PHOSPHINE DERIVATIVE; SIALIC ACID;

ARTICLE; BIOSYNTHESIS; BIOTINYLATION; CELL INTERACTION; CHEMICAL REACTION; FLOW CYTOMETRY; HELA CELL; HUMAN; HUMAN CELL; LEUKEMIA CELL LINE; PRIORITY JOURNAL;

ACETYLATION; AZIDES; BIOTIN; BIOTINYLATION; CELL MEMBRANE; FLOW CYTOMETRY; FLUORESCENT DYES; GLYCOCONJUGATES; HELA CELLS; HEXOSAMINES; HUMANS; JURKAT CELLS; KETONES; OXIDATION-REDUCTION; PHOSPHINES; SOLUBILITY; SULFHYDRYL COMPOUNDS;

EID: 0034677879     PISSN: 00368075     EISSN: None     Source Type: Journal    
DOI: 10.1126/science.287.5460.2007     Document Type: Article

References (18)

1. K. A. Winans and C. R. Bertozzi, Chem. Biol. 5, R313 (1998).
2. L. K. Mahal, K. J. Yarema, C. R. Bertozzi, Science 276, 1125 (1997).
3. K. J. Yarema, L. K. Mahal, R. E. Bruehl, E. C. Rodriguez, C. R. Bertozzi, J. Biol. Chem. 273, 31168 (1998).
4. G. A. Lemieux, K. J. Yarema, C. L. Jacobs, C. R. Bertozzi, J. Am. Chem. Soc. 121, 4278 (1999).
5. J. H. Lee et al., J. Biol. Chem. 274, 21878 (1999).
6. B. A. Griffin, S. R. Adams, R. Y. Tsien, Science 281, 269 (1998).
7. H. Staudinger and J. Meyer, Helv. Chim. Acta 2, 635 (1919).
8. Y. G. Gololobov and L. F. Kasukhin, Tetrahedron 48, 1353 (1992).
9. 4 and concentrated. The crude product was purified by silica gel chromatography eluting with a gradient of 1:10 to 1:2 EtOAc/hexanes to afford 39 mg (95%) of acetylated 3.
10. 2O was added. The solution was cooled to 4°C for 2 hours and the resulting solid was collected by filtration. The pure product, compound 4, was isolated in 69% yield (245 mg). This compound can be coupled with amines by using standard procedures {such as EDC [1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride] or DCC (1.3-dicyclohexylcarbodiimide) coupling reactions}.
11. Acetylated monosaccharides are metabolized 200-fold more efficiently than the free sugars owing to improved cellular uptake, which is followed by deacetylation by cytosolic esterases [C. L Jacobs and C. R. Bertozzi unpublished results; A. K. Sarkar, T. A. Fritz, W. H. Taylor, J. D. Esko, Proc. Natl. Acad. Sci. U.S.A. 92, 3323 (1995)].
12. Acetylated monosaccharides are metabolized 200-fold more efficiently than the free sugars owing to improved cellular uptake, which is followed by deacetylation by cytosolic esterases [C. L Jacobs and C. R. Bertozzi unpublished results; A. K. Sarkar, T. A. Fritz, W. H. Taylor, J. D. Esko, Proc. Natl. Acad. Sci. U.S.A. 92, 3323 (1995)].
13. E. Saxon and C. R. Bertozzi, data not shown.
14. I. L. Cartwright, D. W. Hutchinson, V. W. Armstrong, Nucleic Acids Res. 3, 2331 (1976).
15. Retrovir (zidovudine), Glaxo Wellcome.
16. J. C. M vanHest and D. A. Tirrell, FEBS Lett. 428, 68 (1998).
17. M. W. Nowak et al., Science 268, 439 (1995).
18. We acknowledge generous funding from the W. M. Keck Foundation, Glaxo Wellcome, and the Burroughs Wellcome Fund. E.S. was supported by a Howard Hughes Medical Institute Predoctoral Fellowship. This research was supported by the Office of Naval Research, grant N00014-98-1-0605 and order N00014-98-F-0402 through the U.S. Department of Energy under contract DE-AC03-76SF00098, and by the National Institutes of Health (GM58867-01).