Parallel chemoenzymatic synthesis of sialosides containing a C5-diversified sialic acid

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 20, 2009, Pages 5869-5871

  Cao, Hongzhi ^a   Muthana, Saddam ^a   Li, Yanhong ^a   Cheng, Jiansong ^a   Chen, Xi ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Carbohydrates; Chemoenzymatic synthesis; Enzymes; Parallel synthesis; Sialic acid; Sialosides

Indexed keywords

2 AZIDO 2 DEOXY MANNOSE; CARBOHYDRATE DERIVATIVE; N ACETOXYACETYLNEURAMINIC ACID; N ACETYLNEURAMINIC ACID; N AZIDOACETYLNEURAMINIC ACID; N GLYCOLOYLNEURAMINIC ACID; N METHOXYACETYLNEURAMINIC ACID; NEURAMINIC ACID; SIALIC ACID; SIALOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; QUANTITATIVE ASSAY; REACTION TIME; SIALYLATION;

BIOCATALYSIS; GLYCOSIDES; N-ACETYLNEURAMINIC ACID; N-ACYLNEURAMINATE CYTIDYLYLTRANSFERASE; OXO-ACID-LYASES; SIALYLTRANSFERASES;

EID: 70349202122     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.08.078     Document Type: Article

References (41)

1. Schauer R. Adv. Carbohydr. Chem. Biochem. 40 (1982) 131
2. Angata T., and Varki A. Chem. Rev. 102 (2002) 439
3. Hedlund M., Padler-Karavani V., Varki N.M., and Varki A. Proc. Natl. Acad. Sci. U.S.A. 105 (2008) 18936
4. Padler-Karavani V., Yu H., Cao H., Chokhawala H., Karp F., Varki N., Chen X., and Varki A. Glycobiology 18 (2008) 818
5. Varki A. Trends Mol. Med. 14 (2008) 351
6. Seeberger P.H., and Werz D.B. Nature 446 (2007) 1046
7. Dube D.H., and Bertozzi C.R. Nat. Rev. Drug Disc. 4 (2005) 477
8. Ress D.K., and Linhardt R.J. Curr. Org. Synth. 1 (2004) 31
9. Ando H., and Imamura A. Trends Glycosci. Glycotech. 16 (2004) 293
10. Halcomb R.L., and Chappell M.D. J. Carbohydr. Chem. 21 (2002) 723
11. Boons G.J., and Demchenko A.V. Chem. Rev. 100 (2000) 4539
12. Okamoto K., and Goto T. Tetrahedron 46 (1990) 5835
13. Varki A. Biochimie 83 (2001) 615
14. Malykh Y.N., Schauer R., and Shaw L. Biochimie 83 (2001) 623
15. Baskin J.M., Prescher J.A., Laughlin S.T., Agard N.J., Chang P.V., Miller I.A., Lo A., Codelli J.A., and Bertozzi C.R. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 16793
16. Laughlin S.T., Baskin J.M., Amacher S.L., and Bertozzi C.R. Science 320 (2008) 664
17. Prescher J.A., Dube D.H., and Bertozzi C.R. Nature 430 (2004) 873
18. Pan Y.B., Chefalo P., Nagy N., Harding C., and Guo Z.W. J. Med. Chem. 48 (2005) 875
19. Jacobs C.L., Goon S., Yarema K.J., Hinderlich S., Hang H.C., Chai D.H., and Bertozzi C.R. Biochemistry 40 (2001) 12864
20. Pan Y.B., Ayani T., Nadas J., Wen S.M., and Guo Z.W. Carbohydr. Res. 339 (2004) 2091
21. De Meo C., and Priyadarshani U. Carbohydr. Res. 343 (2008) 1540
22. Ando H., Koike Y., Ishida H., and Kiso M. Tetrahedron Lett. 44 (2003) 6883
23. Hanashima S., Tomiya T., Ishikawa D., Akai S., and Sato K.-I. Carbohydr. Res. 334 (2009) 959
24. Crich D., and Wu B. Org. Lett. 10 (2008) 4033
25. Laurent N., Voglmeir J., and Flitsch S.L. Chem. Commun. (2008) 4400
26. Stevens J., Blixt O., Paulson J.C., and Wilson I.A. Nat. Rev. Microbiol. 4 (2006) 857
27. Huang C.Y., Thayer D.A., Chang A.Y., Best M.D., Hoffmann J., Head S., and Wong C.H. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 15
28. Blixt O., and Razi N. Methods Enzymol. 415 (2006) 137
29. Yu H., and Chen X. Org. Biomol. Chem. 5 (2007) 865
30. Mehta S., Gilbert M., Wakarchuk W.W., and Whitfield D.M. Org. Lett. 2 (2000) 751
31. Hayashi M., Tanaka M., Itoh M., and Miyauchi H. J. Org. Chem. 61 (1996) 2938
32. Cao H.Z., Huang S.S., Cheng J.S., Li Y.H., Muthana S., Son B., and Chen X. Carbohydr. Res. 343 (2008) 2863
33. Ito Y., and Paulson J.C. J. Am. Chem. Soc. 115 (1993) 1603
34. Yu H., Chokhawala H.A., Huang S., and Chen X. Nat. Protoc. 1 (2006) 2485
35. Yu H., Huang S., Chokhawala H., Sun M., Zheng H., and Chen X. Angew. Chem., Int. Ed. 45 (2006) 3938
36. Yu H., Chokhawala H., Karpel R., Yu H., Wu B., Zhang J., Zhang Y., Jia Q., and Chen X. J. Am. Chem. Soc. 127 (2005) 17618
37. Yu H., Yu H., Karpel R., and Chen X. Bioorg. Med. Chem. 12 (2004) 6427
38. Alper P.B., Hung S.C., and Wong C.H. Tetrahedron Lett. 37 (1996) 6029
39. Muthana S., Yu H., Cao H.Z., Cheng J.S., and Chen X. J. Org. Chem. 74 (2009) 2928
40. Bayley H., Standring D.N., and Knowles J.R. Tetrahedron Lett. 19 (1978) 3633
41. Cao H., and Yu B. Tetrahedron Lett. 46 (2005) 4337