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Volumn 20, Issue 5, 2009, Pages 582-585

Synthesis of di- and tetrasaccharide containing 6-deoxytalose from the O-antigenic polysaccharide of B. pseudomallei strain 304b

Author keywords

6 Deoxytalose; Glucose; Oligosaccharide; Rhamnose

Indexed keywords

EID: 62849111260 PISSN: 10018417 EISSN: None Source Type: Journal
DOI: 10.1016/j.cclet.2009.01.007 Document Type: Article

Times cited : (11)

References (18)

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14
- 62849092769
- Crystallographic data of 6 have been deposited with the Cambridge Crystallographic Data Centre as Supplementary Publication with CCDC No. 694597. Copies of the data can be obtained free of charge on application with the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK fax: +44 1223 336 033. email: deposit@ccdc.cam.ac.uk.
- Crystallographic data of 6 have been deposited with the Cambridge Crystallographic Data Centre as Supplementary Publication with CCDC No. 694597. Copies of the data can be obtained free of charge on application with the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336 033. email: deposit@ccdc.cam.ac.uk.

15
- 62849102629
- 12: Foamy solid; 83, α]D25, 204.2 (c 1.0 CHCl3, 1H NMR (300 MHz,CDCl3, δ ppm, 0.86 (d, 3H, J 6.3 Hz, CH3, 3.78 (s, 3H, OCH3, 4.14 (m, 1H, H-5Glup, 4.24 (m, 1H, H-5Talp, 4.53-4.65 (m, 2H, 4.78 (dd, 1H, J2,3, J3,4, 3.9 Hz, H-3Talp, 5.30 (d, 1H, J1,2 7.8 Hz, H-1Glup, 5.48 (dd, 1H, J1,2 7.8 Hz, J2,3 9.6 Hz, H-2Glup, 5.54-5.62 (m, 3H, 5.67 (d, 1H, J1,21.2 Hz, H-1Talp, 5.91 (dd, 1H, J2,3, J3,4, 9.6 Hz, H-3Glup, 6.77-8.02 m, 34H, MALDI-TOF MS calcd. for C61H52O17: 1056.3 [M, found: 1079.1 [M, Na, anal. Calcd. for C61H52O17: C 69.31, H 4.96; found: C 69.19, H 5.12
- 17: C 69.31, H 4.96; found: C 69.19, H 5.12.

16
- 62849112109
- 14: Foamy solid; 70, α]D25, 216.0 (c 1.0 CHCl3, 1H NMR (300 MHz, D2O, δ ppm, 0.64 (d, 3H, J 6.2 Hz, H-6Talp, 1.08 (d, 3H, J 6.4 Hz, H-6Talp, 3.79 (s, 3H, OCH3, 4.19 (dd, 1H, J2,3, J3,4, 3.8 Hz, H-3Talp, 4.66 (d, 1H, J1,2 8.0 Hz, H-1Glup, 4.74 (dd, 1H, J2,3, J3,4, 3.6 Hz, H-3Talp, 5.14 (d, 1H, J1,2 1.0 Hz, H-1Talp, 5.22 (d, 1H, J1,2 7.8 Hz, 1H, H-1Glup, 5.67 (s, 1H, H-1Talp, 13C NMR (300 MHz, D2O, δ ppm, δ 15.5, 16.2 (2 C-6Talp, 97.38, 97.65, 99.16, 99.87 4 C-1, MALDI-TOF MS calcd. for C108H92O31: 1884.6 [M, found: 1907.5 [M, Na, anal. calcd. for C108H92O31: C 68.78, H 4.92; found: C 68.80
- 31: C 68.78, H 4.92; found: C 68.80, H 4.66.

17
- 62849126851
- II: Foamy solid; 80, α]D25, 45.8 (c 0.5 H2O, 1H NMR (300 MHz, D2O, δ ppm, δ 1.15 (d, J 6.2 Hz, 3H, H-6Talp, 3.73 (s, 3H, OCH3, 4.63 (d, J 7.8 Hz, 1H, H-1Glup, 5.45 (s, 1H, H-1Talp, 6.89-7.04 m, 4H, MALDI-TOF MS calcd. for C19H28O11: 432.2 [M, found: 455.1 [M, Na, ESIMS m/z calcd. for [C19H28O11]Na, 455.1529. Found: 455.1532
- +: 455.1529. Found: 455.1532.

18
- 62849114768
- III: Foamy solid; 75, α]D25, 55.8 (c 1.0 H2O, 1H NMR (300 MHz, D2O, δ ppm, 1.15 (d, 3H, J 6.2 Hz, H-6Talp, 1.20 (d, 3H, J 6.4 Hz, H-6Talp, 3.75 (s, 3H, OCH3, 4.60 (d, 1H, J 7.8 Hz, H-1Glup, 4.65 (d, 1H, J 7.8 Hz, H-1Glup, 5.47 (s, 1H, H-1Talp, 5.47 (s, 1H, H-1Talp, 6.90-7.05 (m, 4H, 13C NMR (300 MHz, D2O, δ ppm, 15.6, 15.7 (2 C-6Talp, 99.85 101.28, 101.34, 101.43 4 C-1, MALDI-TOF MS calcd. for C31H48O20: 740.3 [M, found: 763.5 [M, Na, ESIMS m/z calcd. for [C31H48O20]Na, 763.2637. Found: 763.2635
- +: 763.2637. Found: 763.2635.

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