Synthesis of UDP-GlcNAc derivatives modified at OH-4 as potential chain-terminators of chitin biosynthesis

A series of UDP-GlcNAc derivatives and precursors that have been modified at the 4-position were synthesised from N-acetyl glucosamine as potential chain terminators of chitin biosynthesis. None of the UDP-derivatives or the precursors tested displayed any significant anti-fungal activity in cell adhesion or germination assays on the dermatophyte Trichophyton rubrum.

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Dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2-deoxy-4-O-methyl-α-d-glucopyranosideC37H38NO11PEe = 100%[α]D23=+46.3 (c 1.0, CHCl3)Source of chirality: N-acetyl-d-glucosamine

Dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy- α-d-xylo-hexopyranosideC36H36NO10PEe = 100%[α]D23=+58.5 (c 1.0, CHCl3)Source of chirality: N-acetyl-d-glucosamine

Dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-d-glucopyranosideC36H35FNO10PEe = 100%[α]D23=+59.9 (c 1.0, CHCl3)Source of chirality: N-acetyl-d-glucosamine

Dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-azido-α-d-glucopyranosideC36H35N4O10PEe = 100%[α]D20=+90.2 (c 0.5, MeOH)Source of chirality: N-acetyl-d-glucosamine

Uridinediphosphoryl-2-acetamido-2,4-dideoxy-4-O-methyl-α-d-glucopyranoside, ditriethylammonium saltC30H59N5O17P2Ee = 100%[α]D18=+40.8 (c 1.0, MeOH)Source of chirality: N-acetyl-d-glucosamine, d-uridine

Uridinediphosphoryl-2-acetamido-2,4-dideoxy-α-d-xylo-hexopyranoside, ditriethylammonium saltC29H57N5O16P2Ee = 100%[α]D18=+40.2 (c 1.0, MeOH)Source of chirality: N-acetyl-d-glucosamine, d-uridine

Uridinediphosphoryl-2-acetamido-2,4-dideoxy-4-fluoro-α-d-glucopyranoside, ditriethylammonium saltC29H56FN5O16P2Ee = 100%[α]D18=+45.0 (c 0.1, MeOH)Source of chirality: N-acetyl-d-glucosamine, d-uridine

Uridinediphosphoryl-2,4-diacetamido-2,4-dideoxy-α-d-glucopyranoside, ditriethylammonium saltC31H60N6O17P2Ee = 100%[α]D18=+41.6 (c 0.5, MeOH)Source of chirality: N-acetyl-d-glucosamine, d-uridine