Synthesis of branched arabinofuranose pentasaccharide fragment of mycobacterial arabinans as 2-azidoethyl glycoside

Carbohydrate Research

Volumn 357, Issue , 2012, Pages 62-67

  Fedina, Ksenia G ^a,b   Abronina, Polina I ^a   Podvalnyy, Nikita M ^a   Kondakov, Nikolay N ^a   Chizhov, Alexander O ^a   Torgov, Vladimir I ^a   Kononov, Leonid O ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b RUSSIAN ACADEMY OF SCIENCES   (Russian Federation)

Author keywords

1,2 cis Glycosylation; Aglycon; Arabinofuranose; Azide; Pentasaccharide

Indexed keywords

1,2-CIS-GLYCOSYLATION; AGLYCON; ARABINOFURANOSE; AZIDE; PENTASACCHARIDES;

ESTERIFICATION; GLYCOSYLATION;

SUGARS;

2 AZIDOETHYL GLYCOSIDE; ARABINOSE DERIVATIVE; ARABINOXYLAN; PENTASACCHARIDE; THIOGLYCOSIDE; TRIFLUOROACETAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BENZYLATION; CATALYSIS; CHROMATOGRAPHY; CLICK CHEMISTRY; DIASTEREOISOMER; GLYCOSIDATION; GLYCOSYLATION; HYDROGENOLYSIS; MYCOBACTERIUM; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

ARABINOSE; AZIDES; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; CELL WALL; GLYCOSYLATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; MYCOBACTERIUM TUBERCULOSIS; OLIGOSACCHARIDES, BRANCHED-CHAIN; POLYSACCHARIDES;

EID: 84863724268     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2012.05.021     Document Type: Article

References (59)

1. Health Topics: Tuberculosis; World Health Organization: Geneva, 2012. http://www.who.int/topics/tuberculosis/en (accessed March 15 2012).
2. Tuberculosis Fact Sheet No. 104; World Health Organization: Geneva, November 2010. http://www.who.int/mediacentre/factsheets/fs104/en/index.html (accessed March 15 2012).
3. C. Chiang, and W.W. Yew Int. J. Tuberc. Lung Dis. 13 2009 304 311
4. P.J. Brennan, and H. Nikaido Annu. Rev. Biochem. 64 1995 29 63
5. P.J. Brennan Tuberculosis 83 2003 91 97
6. D. Kaur, M.E. Guerin, H. Skovierová, P.J. Brennan, and M. Jackson Adv. Appl. Microbiol. 69 2009 23 78
7. M. Joe, Y. Bai, R.C. Nacario, and T.L. Lowary J. Am. Chem. Soc. 129 2007 9885 9901
8. A. Ishiwata, H. Akao, and Y. Ito Org. Lett. 8 2006 5525 5528
9. Y.J. Lee, K. Lee, E.H. Jung, H.B. Jeon, and K.S. Kim Org. Lett. 7 2005 3263 3266
10. B. Fraser-Reid, J. Lu, K.N. Jayaprakash, and J.C. Lopez Tetrahedron: Asymmetry 17 2006 2449 2463
11. X.-Y. Liang, L.-M. Deng, X. Liu, and J.-S. Yang Tetrahedron 66 2010 87 93
12. K. Marotte, S. Sanchez, T. Bamhaoud, and J. Prandi Eur. J. Org. Chem. 2003 3587 3598
13. H. Yin, F.W. D'Souza, and T.L. Lowary J. Org. Chem. 67 2002 892 903
14. R.R. Gadikota, C.S. Callam, B.J. Appelmelk, and T.L. Lowary J. Carbohydr. Chem. 22 2003 459 480
15. Tam, P.-H.; Lowary, T. L. In Carbohydr. Chem.; Rauter, A. P.; Lindhorst, T. K., Eds.; the Royal Society of Chemistry, 2010; Vol. 36, pp 38-63, and references cited therein.
16. H.B. Mereyala, S. Hotha, and M.K. Gurjar Chem. Commun. 1998 685 686
17. F.W. D'Souza, and T.L. Lowary Org. Lett. 2 2000 1493 1495
18. S. Sanchez, T. Bamhaoud, and J. Prandi Tetrahedron Lett. 41 2000 7447 7452
19. A. Ishiwata, H. Akao, Y. Ito, M. Sunagawa, N. Kusunose, and Y. Kashiwazaki Bioorg. Med. Chem. 14 2006 3049 3061
20. Ito, Y. 16th European Carbohydrate Symposium Eurocarb 16, Sorrento, Italy, July 3-7, 2011. E-Book of Abstracts, p 27, IL 01.
21. A. Ishiwata, and Y. Ito J. Am. Chem. Soc. 133 2011 2275 2291
22. P.I. Abronina, N.M. Podvalnyy, T.M. Melnikova, A.I. Zinin, K.G. Fedina, V.V. Kachala, V.I. Torgov, L.O. Kononov, E.A. Panfertsev, E.V. Baranova, V.V. Mochalov, V.I. Dyatlova, and S.F. Biketov Russ. Chem. Bull. 59 2010 2333 2337
23. G. Magnusson, A.Y. Chernyak, J. Kihlberg, and L.O. Kononov Y.C. Lee, R.T. Lee, Neoglycoconjugates: Preparation and Application 1994 Academic Press Inc. San Diego, California 53 143
24. S. Dedola, S.A. Nepogodiev, and R.A. Field Org. Biomol. Chem. 5 2007 1006 1017
25. P. Cheshev, A. Marra, and A. Dondoni Org. Biomol. Chem. 4 2006 3225 3227
26. S. Hotha, and S. Kashyap J. Org. Chem. 71 2006 364 367
27. A. Dondoni Chem. Asian J. 2 2007 700 708
28. A. Marra, L. Moni, D. Pazzi, A. Corallini, D. Bridi, and A. Dondoni Org. Biomol. Chem. 6 2008 1396 1409
29. C.W. Tornoe, C. Christiensen, and M. Meldal J. Org. Chem. 67 2002 3057 3064
30. A. Dondoni Angew. Chem., Int. Ed. 47 2008 8995 8997
31. D. Macmillan, and J. Blanc Org. Biomol. Chem. 4 2006 2847 2850
32. K.D. Bodine, D.Y. Gin, and M.S. Gin J. Am. Chem. Soc. 126 2004 1638 1639
33. M. Meldal, and C.W. Tornoe Chem. Rev. 108 2008 2952 3015
34. B.L. Wilkinson, L.F. Bornaghi, S.-A. Poulsen, and T.A. Houston Tetrahedron 62 2006 8115 8125
35. C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004 2021
36. V. Hong, S.I. Presolski, C. Ma, and M.G. Finn Angew. Chem., Int. Ed. 48 2009 9879 9883
37. F. Fazio, M.C. Bryan, O. Blixt, J.C. Paulson, and C.-H. Wong J. Am. Chem. Soc. 124 2002 14397 14402
38. X. Zhang, X. Yang, and S. Zhang Synth. Commun. 39 2009 830 844
39. C.R. Becer, R. Hoogenboom, and U.S. Schubert Angew. Chem., Int. Ed. 48 2009 2 11
40. V.D. Bock, H. Hiemstra, and J.H. van Maarseveen Eur. J. Org. Chem. 2006 51 68
41. V. Rostovstev, L.G. Green, V.V. Fokin, and B.K. Sharpless Angew. Chem., Int. Ed. 41 2002 2596 2599
42. J.-F. Lutz Angew. Chem., Int. Ed. 47 2008 2182 2184
43. N.J. Agard, J.A. Prescher, and C.R. Bertozzi J. Am. Chem. Soc. 126 2004 15046 15047
44. N.E. Mbua, J. Guo, M.A. Wolfert, R. Steet, and G.-J. Boons ChemBioChem 12 2011 1912 1921
45. A.Y. Chernyak, G.V.M. Sharma, L.O. Kononov, P. Radha Krishna, A.B. Levinsky, N.K. Kochetkov, and A.V. Rama Rao Carbohydr. Res. 223 1992 303 309
46. B.L. Wilkinson, H. Long, E. Sim, and A.J. Fairbanks Bioorg. Med. Chem. Lett. 18 2008 6265 6267
47. M. Wilstermann, L.O. Kononov, U. Nilsson, A.K. Ray, and G. Magnusson J. Am. Chem. Soc. 117 1995 4742 4754
48. P.J. Garegg, P. Konradsson, I. Kvarnström, T. Norberg, S.C.T. Svensson, and B. Wigilius Acta Chem. Scand. B39 1985 569 577
49. A.V. Kornilov, A.A. Sherman, L.O. Kononov, A.S. Shashkov, and N.E. Nifant'ev Carbohydr. Res. 329 2000 717 730
50. O.N. Yudina, A.A. Sherman, and N.E. Nifantiev Carbohydr. Res. 332 2001 363 371
51. Y. Wang, S. Maguire-Boyle, R.T. Dere, and X. Zhu Carbohydr. Res. 343 2008 3100 3106
52. N.M. Podvalnyy, S.L. Sedinkin, P.I. Abronina, A.I. Zinin, K.G. Fedina, V.I. Torgov, and L.O. Kononov Carbohydr. Res. 346 2011 7 15
53. P.I. Abronina, N.M. Podvalnyy, S.L. Sedinkin, K.G. Fedina, A.I. Zinin, A.O. Chizhov, V.I. Torgov, and L.O. Kononov Synthesis 44 2012 1219 1225
54. P.I. Abronina, S.L. Sedinkin, N.M. Podvalnyy, K.G. Fedina, A.I. Zinin, V.I. Torgov, and L.O. Kononov Tetrahedron Lett. 52 2011 1794 1796
55. X. Zhu, S. Kawatkar, Y. Rao, and G.-J. Boons J. Am. Chem. Soc. 128 2006 11948 11957
56. D. Crich, C.M. Pedersen, A.A. Bowers, and D.J. Wink J. Org. Chem. 72 2007 1553 1565
57. P.G.M. Wuts, and T.W. Greene Protective Groups in Organic Synthesis 4th ed. 2007 John Wiley & Sons Hoboken, New Jersey pp 406-410
58. P.J. Kocienski Protecting Groups 3rd ed. 2004 Georg Thieme Stuttgart pp 28-41, 110-114
59. A. Imamura, and T.L. Lowary Org. Lett. 12 2010 3686 3689