Erythropoietin derived by chemical synthesis

Science

Volumn 342, Issue 6164, 2013, Pages 1357-1360

  Wang, Ping ^a   Dong, Suwei ^a   Shieh, Jae Hung ^a   Peguero, Elizabeth ^a   Hendrickson, Ronald ^a   Moore, Malcolm A S ^a   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARAGINE LINKED OLIGOSACCHARIDE; ASPARTIC ACID; CHITOBIOSE; CYSTEINE; ERYTHROPOIETIN; GLYCOPHORIN; MANNOSE; RECOMBINANT ERYTHROPOIETIN; SIALIC ACID;

BIOCHEMISTRY; CARBOHYDRATE; PEPTIDE; PROTEIN;

AMIDATION; AMINO ACID SEQUENCE; ARTICLE; CARBOHYDRATE SYNTHESIS; CELL PROLIFERATION; ELECTROPHORETIC MOBILITY; IN VIVO STUDY; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN GLYCOSYLATION; PROTEIN SYNTHESIS; RETICULOCYTE; SOLID;

MUS;

EID: 84890107812     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1245095     Document Type: Article

References (39)

1. S. Elliott, M. A. Foote, G. Molineux, Erythropoietins, Erythropoietic Factors, and Erythropoiesis (Birkhäuser, Basel, Switzerland, ed. 2, 2009).
2. A. J. Sytkowski, Erythropoietin (Wiley-VCH, Weinheim, Germany, 2004).
3. R. S. Rush et al., Anal. Chem. 67, 1442-1452 (1995).
4. P. Wang et al., Angew. Chem. Int. Ed. 51, 11576-11584 (2012).
5. R. M. Wilson, S. Dong, P. Wang, S. J. Danishefsky, Angew. Chem. Int. Chem. 52, 7646-7665 (2013).
6. During the course of these investigations, ongoing studies from other laboratories provided striking results in reaching congeners of various sorts with promising erthyropoietic activity. This work is summarized in (5) and includes references (31, 37, 38).
7. B. Wu et al., Tetrahedron Lett. 47, 5577-5579 (2006).
8. B. Wu et al., Tetrahedron Lett. 47, 8009-8011 (2006).
9. S. J. Danishefsky, M. T. Bilodeau, Angew. Chem. Int. Ed. Engl. 35, 1380-1419 (1996).
10. S. J. Danishefsky, J. R. Allen, Angew. Chem. Int. Ed. 39, 836-863 (2000).
11. J. B. Schwarz et al., J. Am. Chem. Soc. 121, 2662-2673 (1999).
12. There are over 50 glycoforms of recombinant EPO containing combinations of bi-, tri-, and tetraantennary carbohydrate domains, which have not been separated or fully characterized [see (13)].
13. H. Sasaki, B. Bothner, A. Dell, M. Fukuda, J. Biol. Chem. 262, 12059 -12076 (1987).
14. M. Takeuchi, A. Kobata, Glycobiology 1, 337-346 (1991).
15. S. R. Hamilton et al., Science 313, 1441-1443 (2006).
16. J. H. Nett et al ., J. Biotechnol. 157, 198-206 (2012).
17. P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. Kent, Science 266, 776-779 (1994).
18. Q. Wan, S. J. Danishefsky, Angew. Chem. Int. Ed. 46, 9248-9252 (2007).
19. L. Z. Yan, P. E. Dawson, J. Am. Chem. Soc. 123, 526-533 (2001).
20. J. D. Warren, J. S. Miller, S. J. Keding, S. J. Danishefsky, J. Am. Chem. Soc. 126, 6576 -6578 (2004).
21. G. Chen et al., J. Am. Chem. Soc. 128, 7460-7462 (2006).
22. S. Dong, S. Shang, Z. Tan, S. J. Danishefsky, Isr. J. Chem. 51, 968- 976 (2011).
23. P. Wang, B. Aussedat, Y. Vohra, S. J. Danishefsky, Angew. Chem. Int. Ed. 51, 11571-11575 (2012).
24. V. Ullmann et al., Angew. Chem. Int. Ed. 51, 11566-11570 (2012).
25. D. Bang, S. B. Kent, Angew. Chem. Int. Ed. 43, 2534-2538 (2004).
26. S. Sakakibara, Biopolymers 37, 17-28 (1995).
27. S. Liu, B. L. Pentelute, S. B. Kent, Angew. Chem. Int. Ed. 51, 993-999 (2012).
28. The mass spectrum of 10 (figs. S24 and S25) is supportive of the assignment. However, as is the case with previous attempts at obtaining high-quality readouts from extensively glycosylated polysialic acid-containing domains, this attempt has not been fully successful.
29. E. Llop, R. Gutiérrez-Gallego, J. Segura, J. Mallorquí, J. A. Pascual, Anal. Biochem. 383, 243-254 (2008).
30. V. P. Saxena, D. B. Wetlaufer, Biochemistry 9, 5015-5023 (1970).
31. G. G. Kochendoerfer et al., Science 299, 884-887 (2003).
32. L. O. Narhi et al., Protein Eng. 14, 135-140 (2001).
33. M. A. Recny, H. A. Scoble, Y. Kim, J. Biol. Chem. 262, 17156-17163 (1987).
34. R. S. Syed et al., Nature 395, 511-516 (1998).
35. R. B. Merrifield, J. Am. Chem. Soc. 85, 2149-2154 (1963).
36. T. Wang, S. J. Danishefsky, Proc. Natl. Acad. Sci. U.S.A. 110, 11708-11713 (2013).
37. K. Hirano, D. Macmillan, K. Tezuka, T. Tsuji, Y. Kajihara, Angew. Chem. Int. Ed. Engl. 48, 9557-9560 (2009).
38. M. Murakami, R. Okamoto, M. Izumi, Y. Kajihara, Angew. Chem. Int. Ed. Engl. 51, 3567-3572 (2012).
39. Information on materials and methods, including spectroscopic data of new compounds, is available on Science Online.