Syntheses of TN building blocks Nα-(9- fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D- galactopyranosyl)-L-serine/L-threonine pentafluorophenyl esters: Comparison of protocols and elucidation of side reactions

Carbohydrate Research

Volumn 340, Issue 7, 2005, Pages 1273-1285

  Liu, Mian ^a,b   Young Jr , Victor G ^b   Lohani, Sachin ^a   Live, David ^a   Barany, George ^b  

^a UNIVERSITY OF MINNESOTA   (United States)

^b University of Minnesota   (United States)

Author keywords

Dehydroalanine; Glycopeptide synthetic building blocks; Glycosylation; Metal ion carbohydrate complexes; Side reactions; Z Dehydrothreonine

Indexed keywords

BYPRODUCTS; COLUMN CHROMATOGRAPHY; COMPLEXATION; ESTERS; LITHIUM COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

AZIDONITRATION; LITHIUM BROMIDE; LITHIUM IODIDE; SODIUM IODIDES;

ANTIGENS;

3,4,6 TRI O ACETYL 2 AZIDO 2 DEOXY ALPHA DEXTRO GALACTOPYRANOSYL BROMIDE; 3,4,6 TRI O ACETYL 2 AZIDO 2 DEOXY BETA DEXTRO GALACTOPYRANOSYL CHLORIDE; 3,4,6 TRI O ACETYL DEXTRO GALACTAL; ACETIC ACID DERIVATIVE; ACETONITRILE D3; ACETONITRILE DERIVATIVE; ANTIGEN; ESTER DERIVATIVE; LITHIUM BROMIDE; LITHIUM DERIVATIVE; LITHIUM IODIDE; N ACETYL 3,4,6 TRI O ACETYL 2 AZIDO 2 DEOXY ALPHA DEXTRO GALACTOPYRANOSYLAMINE; N ALPHA (9 FLUORENYLMETHOXYCARBONYL) O (3,4,6 TRI O ACETYL 2 AZIDO 2 DEOXY ALPHA DEXTRO GALACTOPYRANOSYL)SERINE PENTAFLUOROPHENYL ESTER; N ALPHA (9 FLUORENYLMETHOXYCARBONYL) O (3,4,6 TRI O ACETYL 2 AZIDO 2 DEOXY ALPHA DEXTRO GALACTOPYRANOSYL)THREONINE PENTAFLUOROPHENYL ESTER; N ALPHA (9 FLUORENYLMETHOXYCARBONYL)SERINE PENTAFLUOROPHENYL ESTER; N ALPHA (9 FLUORENYLMETHOXYCARBONYL)THREONINE PENTAFLUOROPHENYL ESTER; SODIUM IODIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; COMPARATIVE STUDY; COMPLEX FORMATION; GLYCOSYLATION; ISOLATION PROCEDURE; NITRATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; REACTION ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 18044391306     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2005.02.029     Document Type: Article

References (29)

1. P. Van den Steen, P.M. Rudd, R.A. Dwek, and G. Opdenakker Crit. Rev. Biochem. Mol. Biol. 33 1998 151 208
2. H. Kunz Angew. Chem., Int. Ed. Engl. 26 1987 294 308
3. D. Sames, X.T. Chen, and S.J. Danishefsky Nature 389 1997 587 591
4. S.D. Kuduk, J.B. Schwarz, X.T. Chen, P.W. Glunz, D. Sames, G. Ragupathi, P.O. Livingston, and S.J. Danishefsky J. Am. Chem. Soc. 120 1998 12474 12485
5. H. Hojo, and Y. Nakahara Curr. Protein Pept. Sci. 1 2000 23 48
6. T. Bielfeldt, S. Peters, M. Meldal, K. Bock, and H. Paulsen Angew. Chem., Int. Ed. Engl. 31 1992 857 859
7. B. Lüning, T. Norberg, and J. Tejbrant Glycoconjugate J. 6 1989 5 19
8. S. Peters, T. Bielfeldt, M. Meldal, K. Bock, and H. Paulsen J. Chem. Soc., Perkin Trans. 1 9 1992 1163 1171
9. H. Paulsen, T. Bielfeldt, S. Peters, M. Meldal, and K. Bock Liebigs Ann. Chem. 4 1994 369 379
10. J.E. Yule, T.C. Wong, S.S. Gandhi, D. Qiu, M.A. Riopel, and R.R. Koganty Tetrahedron Lett. 36 1995 6839 6842
11. T.L. Gururaja, N. Ramasubbu, and M.J. Levine Lett. Pept. Sci. 3 1996 79 88
12. M. Liu, D. Live, and G. Barany Chimica Oggi 22 2004 30 34
13. R.U. Lemieux, and R.M. Ratcliffe Can. J. Chem. 57 1979 1244 1251
14. A. Vargas-Berenguel, M. Meldal, H. Paulsen, and K. Bock J. Chem. Soc., Perkin Trans. 1 18 1994 2615 2619
15. H. Kunz, and S. Birnbach Angew. Chem., Int. Ed. Engl. 25 1986 360 362
16. H. Paulsen, S. Peters, T. Bielfedt, M. Meldal, and K. Bock Carbohydr. Res. 268 1995 17 34
17. H. Paulsen, A. Richter, V. Sinnwell, and W. Stenzel Carbohydr. Res. 64 1978 339 362
18. J. Broddefalk, U. Nilsson, and J. Kihlberg J. Carbohydr. Chem. 13 1994 129 132
19. O. Srinivas, B. Muktha, S. Radhika, T.N. Guru Row, and N. Jayaraman Carbohydr. Res. 339 2004 1447 1451
20. J.A. Rendleman Adv. Carbohydr. Chem. 21 1966 209 270
21. S.J. Angyal Pure Appl. Chem. 35 1973 131 146
22. S.J. Angyal Adv. Carbohydr. Chem. Biochem. 47 1989 1 43
23. J.F. Verchère, S. Chapelle, F. Xin, and D.C. Crans Prog. Inorg. Chem. 47 1998 837 945
24. S. Yano, and Y. Mikata Bull. Chem. Soc. Jpn. 75 2002 2097 2113
25. C. Somlai, S. Lovas, P. Forgó, R.F. Murphy, and B. Penke Synth. Commun. 31 2001 3633 3640
26. A.M. Jansson, M. Meldal, and K. Bock J. Chem. Soc., Perkin Trans. 1 13 1992 1699 1707
27. SAINT V6.2, Bruker analytical X-ray systems, Madison, WI, 2001
28. R.H. Blessing Acta Crystallogr., Sect. A: Found Crystallogr. 51 1995 33 38
29. SHELXTL V6.10, Bruker Analytical X-ray Systems, Madison, WI, 2000