Chemoenzymatic synthesis of uridine diphosphate-GlcNAc and uridine diphosphate-GalNAc analogs for the preparation of unnatural glycosaminoglycans

Journal of Organic Chemistry

Volumn 77, Issue 3, 2012, Pages 1449-1456

  Masuko, Sayaka ^a   Bera, Smritilekha ^a   Green, Dixy E ^b   Weïwer, Michel ^d   Liu, Jian ^c   Deangelis, Paul L ^b   Linhardt, Robert J ^a  

^a Rensselaer Polytechnic Institute   (United States)

^b UNIVERSITY OF OKLAHOMA COLLEGE OF MEDICINE   (United States)

^c UNC Hamner Institute for Drug Safety Sciences   (United States)

^d BROAD INSTITUTE OF MIT AND HARVARD   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE LINKAGES; CHEMO-ENZYMATIC SYNTHESIS; DIPHOSPHATES; GLYCOSAMINOGLYCANS; GLYCOSYLTRANSFERASES; IN-VITRO; SUGAR NUCLEOTIDES;

AMIDES; ENZYMES;

SUGARS;

4' [2 (1 OXO 2 PROPYN 1 YL)AMINO 2 DEOXY ALPHA DEXTRO GALACTOPYRANOSYL]ESTER URIDINE 5' (TRIHYDROGEN DIPHOSPHATE); 4' [2 (1 OXO 2 PROPYN 1 YL)AMINO 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSYL]ESTER URIDINE 5' (TRIHYDROGEN DIPHOSPHATE); 4' [2 (ACETYLAMINO) 2 DEOXY ALPHA DEXTRO GALACTOPYRANOSYL]ESTER URIDINE 5' (TRIHYDROGEN DIPHOSPHATE); 4' [2 (ACETYLAMINO) 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSYL]ESTER URIDINE 5' (TRIHYDROGEN DIPHOSPHATE); 4' [2 DEOXY 2 [(1 OXO 2 ETHEN 1 YL)AMINO] 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSYL]ESTER URIDINE 5' (TRIHYDROGEN DIPHOSPHATE); 4' [2 DEOXY 2 [(2,2,2 TRIFLUOROACETYL)AMINO] ALPHA DEXTRO GLUCOPYRANOSYL]ESTER URIDINE 5' (TRIHYDROGEN DIPHOSPHATE); 4' [2 DEOXY 2 [(FLUORENYLMETHOXYCARBONYL)AMINO] ALPHA DEXTRO GLUCOPYRANOSYL]ESTER URIDINE 5' (TRIHYDROGEN DIPHOSPHATE); 4' [2 DEOXY 2 [[(1,1 DIMETHYLETHOXY)CARBONYL]AMINO] ALPHA DEXTRO GLUCOPYRANOSYL]ESTER URIDINE 5' (TRIHYDROGEN DIPHOSPHATE); 4' [2 DEOXY 2 [[5 (HEXAHYDRO 2 OXO 1H THIENO [3,4 D]IMIDAZOL 4 YL) 1 OXOPENTYL]AMINO] ALPHA DEXTRO GLUCOPYRANOSYL]ESTER URIDINE 5' (TRIHYDROGEN DIPHOSPHATE); GLYCOSAMINOGLYCAN; GLYCOSYLTRANSFERASE; N ACETYLGALACTOSAMINE 1 PHOSPHATE DERIVATIVE; N ACETYLGLUCOSAMINE 1 PHOSPHATE DERIVATIVE; PHOSPHATE; POLYSACCHARIDE; RESIN; SUGAR NUCLEOTIDE; UNCLASSIFIED DRUG; URIDINE DERIVATIVE; URIDINE DIPHOSPHATE; URIDINE DIPHOSPHATE N ACETYLGALACTOSAMINE; URIDINE DIPHOSPHATE N ACETYLGLUCOSAMINE;

ARTICLE; CARBOHYDRATE SYNTHESIS; COMPARATIVE STUDY; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME IMMOBILIZATION; ENZYME SUBSTRATE; IN VITRO STUDY;

CHEMISTRY TECHNIQUES, SYNTHETIC; ESCHERICHIA COLI PROTEINS; MULTIENZYME COMPLEXES; POLYMERIZATION; URIDINE DIPHOSPHATE N-ACETYLGLUCOSAMINE;

EID: 84863011654     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202322k     Document Type: Article

References (24)

1. van Heijenoort, J. Glycobiology 2001, 11 (3) 25R-36R
2. Wu, A. M. Neurochem. Res. 2002, 27 (7-8) 593-600
3. Capila, I.; Linhardt, R. J. Angew. Chem., Int. Ed. 2002, 41 (3) 391-412
4. Watkins, W. M. Carbohyd. Res. 1986, 149 (1) 1-12
5. Sismey-Ragatz, A. E.; Green, D. E.; Otto, N. J.; Rejzek, M.; Field, R. A.; DeAngelis, P. L. J. Biol. Chem. 2007, 282 (39) 28321-7
6. Karst, N. A.; Linhardt, R. J. Curr. Med. Chem. 2003, 10 (19) 1993-2031
7. Xu, Y.; Masuko, S.; Takieddin, M.; Xu, H.; Liu, R.; Jing, J.; Mousa, S. A.; Linhardt, R. J.; Liu, J. Science 2011, 334 (6055) 498-501
8. Guan, W.; Cai, L.; Fang, J.; Wu, B.; Wang, P. G. Chem. Commun. 2009, 45, 6976-8
9. Guan, W.; Cai, L.; Wang, P. G. Chem.-Eur. J. 2010, 16 (45) 13343-13345
10. Chen, Y.; Thon, V.; Li, Y.; Yu, H.; Ding, L.; Lau, K.; Qu, J.; Hie, L.; Chen, X. Chem. Commun. 2011, 47 (38) 10815-10817
11. Yan, R. B.; Yang, F.; Wu, Y. F.; Zhang, L. H.; Ye, X. S. Tetrahedron Lett. 2005, 46 (52) 8993-8995
12. MacDonald, D. L. J. Org. Chem. 1966, 31 (2) 513-6
13. Ikeda, S.; Shibuya, M.; Iwabuchi, Y. Chem. Commun. 2007, 5, 504-506
14. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41 (14) 2596-2599
15. Liu, T.; Xu, Y.; Chen, M.; Weïwer, M.; Zhou, X.; Bridges, A. S.; DeAngelis, P. L.; Zhang, Q.; Linhardt, R. J.; Liu, J. J. Biol. Chem. 2010, 285 (44) 34240-9
16. Curphey, T. J. J. Org. Chem. 1979, 44 (15) 2805-2807
17. Dondoni, A. Angew. Chem., Int. Ed. 2008, 47 (47) 8995-7
18. Mengin-Lecreulx, D.; van Heijenoort, J. J. Bacteriol. 1994, 176 (18) 5788-95
19. Bintein, F.; Auge, C.; Lubineau, A. Carbohyd. Res. 2003, 338 (11) 1163-1173
20. Faijes, M.; Saura-Valls, M.; Perez, X.; Conti, M.; Planas, A. Carbohyd. Res. 2006, 341 (12) 2055-2065
21. Sala, R. F.; MacKinnon, S. L.; Palcic, M. M.; Tanner, M. E. Carbohyd. Res. 1998, 306 (1-2) 127-136
22. Jing, W.; DeAngelis, P. L. Glycobiology 2003, 13 (10) 661-71
23. Jing, W.; DeAngelis, P. L. Glycobiology 2000, 10 (9) 883-89
24. Chen, M.; Bridges, A.; Liu, J. Biochemistry 2006, 45 (40) 12358-12365