Synthesis of C-3 nitrogen-containing derivatives of N-acetyl-alpha,beta-D-mannosamine as substrates for N-acetylneuraminic acid aldolase.
The synthesis of 3-azido-3-deoxy, 3-amino-3-deoxy and 3-N-tert-butyloxycarbonyl-3-deoxy derivatives of 2-acetamido-2-deoxy-alpha,beta-D-mannose (N-acetyl-alpha,beta-D-mannosamine, ManNAc), is presented. The 3-azido-3-deoxy- and 3-N-tert-butyloxycarbonyl compounds were further characterised as their peracetates. A preliminary study has found that these C-3 nitrogen-substituted derivatives of ManNAc not to be substrates for Neu5Ac aldolase.
Kok
G B
GB
Department of Medicinal Chemistry, Monash University, Victoria, Australia.
Campbell
M
M
Mackey
B L
BL
von Itzstein
M
M
D006595:Hexosamines / Q000138:chemical synthesis* / Q000378:metabolism; D009584:Nitrogen / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D007652:Oxo-Acid-Lyases / Q000378:metabolism*; D013379:Substrate Specificity
D006595:Hexosamines; D007652:Oxo-Acid-Lyases; C018728:N-acetylneuraminate lyase; D009584:Nitrogen; C002022:N-acetylmannosamine