Synthesis of pentaarabinofuranosyl structure motif A of Mycobacterium tuberculosis

Abstract

The first synthesis of motif A, the branched chain arabinofuranosyl pentasaccharide [t-β-Araf-(1 → 2)-α-D-Araf]₂-3,5-α-D-Araf-(1 → 5) which constitutes the major humoral immunological epitope in the arabinogalactan cell wall of Mycobacterium tuberculosis is described.

References

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9. Selected data for 9: δ_H(200 MHz, CDCl₃) for anomeric protons: 5.05 (d, J 4.6), 5.15 (d, J 4.1); δ_C(50 MHz, CDCl₃) for anomeric carbons: 98.5, 100.2; FABMS: 823 (M + Na)⁺. For 10: δ_H(200 MHz, CDCl₃) for anomeric protons: 4.90 (d, J 4.6), 5.05 (s), 5.76 (d, J 4.6); δ_C(50 MHz, CDCl₃) for anomeric carbons: 100.1, 105.3, 105.5; FABMS: 928 (M + Na)⁺. For 11a: δ_H(200 MHz, CDCl₃) for anomeric protons: 4.92 (d, J 4.6), 5.04 (s), 5.18 (d, J 4.7), 5.29 (s), 5.70 (d, J 4.8); δ_C(50 MHz, CDCl₃) for anomeric carbons: 100.1, 100.4, 105.2, 105.5, 106.0; FABMS: 1643 (M + Na)⁺. For 11b: δ_H(200 MHz, CDCl₃) for anomeric protons: 4.90 (d, J 4.70), 5.02 (s), 5.09 (d, J 4.65), 5.29 (d, J 4.8), 5.70 (d, J 4.7); δ_C(50 MHz, CDCl₃) for anomeric carbons: 98.3, 100.2, 100.6, 105.1, 105.5; FABMS: 1643 (M + Na)⁺. For 1a: δ_H(400 MHz, D₂O) for anomeric protons: 4.90 (d, J 4.20), 5.10 (d, J 4.65), 5.15 (s), 5.28 (s), 6.00 (d, J 4.8); δ_C(50 MHz, D₂O) for anomeric carbons: 102.0, 102.1, 106.3, 106.5, 106.9; FABMS: 741 (M + Na)⁺.